Name: 3923-52-2|1,1-Diphenylprop-2-yn-1-ol|97%
Brand: Ambeed
SKU: A157269
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1
[ 119-61-9 ]
[ 1066-26-8 ]
[ 3923-52-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran; xylene at -10 - 20℃;
	With ammonia
	In ammonia

	With ammonia In diethyl ether
	In dimethyl sulfoxide
	With acetylene In tetrahydrofuran; xylene at 20℃; for 16h;	1.1 Benzophenone (50 grams (g) ) was dissolved in a reaction flask containing 200 milliliters (mL) of anhydrous tetrahydrofuran (THF) saturated with acetylene and stirred at room temperature. An 18 weight percent suspension of sodium acetylide in xylene/mineral oil (0.3 mol of sodium acetylide) was added to the reaction flask and the mixture-was stirred. After stirring 16 hours at room temperature under a nitrogen atmosphere, the contents of the reaction flask mixture was added to a 5 weight percent aqueous hydrochloric acid and ice mixture. The resulting mixture was extracted with diethyl ether. The organic layer was separated, washed, and dried over anhydrous sodium sulfate. The solvents, diethylether and THF, were removed under vacuum to yield an oil product containing 1, l-diphenyl-2-propyn-1-ol, which was not purified further but used directly in the next step.
	Stage #1: benzophenone; sodium acetylide In tetrahydrofuran at 0 - 20℃; Stage #2: With water In tetrahydrofuran Cooling with ice;	4.2. Preparation of 3,3-diaryl-3H-naphtho[2,1-b]pyrans (4), general procedure General procedure: Preparation methods of 3,3-diaryl-3H-naphtho[2,1-b]pyrans were generally based on condensation reactions taking place in the apolar solvent as toluene under acid catalysis, which starting from suitable naphthols and propargyl alcohols.[26], [27] and [28]The propargyl alcohol (2) was prepared from the diaryl ketone (1) as outlined in Scheme 1. 10 mmol diaryl ketone (1) was dissolved in 50 mL dry THF and was added dropwise to a solution of 50 mmol sodium acetylide in THF below 0 °C. The mixture was then allowed to stir at room temperature for about 3 h until none of the diaryl ketone (1) remained by TLC examination of the reaction mixture. The reaction mixture was poured into iced water for separation. The organic phase was collected and followed by washing with water (3×50 mL) and then dried (anhyd Na2SO4). The propargyl alcohol was then obtained in the yield of about 80% after the short flash chromatography and was used for subsequent procedure directly.273 mmol propargyl alcohol (2), 3 mmol 2-naphthol derivative (3), and 1.0 g p-toluenesulfonic acid (TsOH) were dissolved in 50 mL toluene. The reaction mixture was refluxed for about 2 h until TLC examination indicated that none of the propargyl alcohol remained. The mixture was cooled to room temperature and washed with 1 mol L-1 NaOH solution (2×50 mL) and water. After drying with anhyd Na2SO4, removal of the toluene by vacuum evaporation gave a dark gum. The pure naphthopyran product was obtained by elution from silica using 10% ethyl acetate/hexane.
	In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; mineral oil at 0 - 20℃;

Reference： [1]Teral, Yannick; Roubaud, Gabriel; Aubert, Claude; Faure, Robert; Campredon, Mylene [Australian Journal of Chemistry, 2005, vol. 58, # 7, p. 517 - 521]
[2]Campbell; Campbell; Eby [Journal of the American Chemical Society, 1938, vol. 60, p. 2882]
[3]Landor,P.D.; Landor,S.R. [Journal of the Chemical Society, 1963, p. 2707 - 2711]
[4]Ried,W.; Koenig,E. [Justus Liebigs Annalen der Chemie, 1972, vol. 757, p. 153 - 169]
[5]Current Patent Assignee: APAX PARTNERS LLP - US6660727, 2003, B1 Location in patent: Page column 14
[6]Current Patent Assignee: ESSILORLUXOTTICA - WO2005/61514, 2005, A1 Location in patent: Page/Page column 40
[7]Location in patent: experimental part Wang, Zhen; Meng, Qinghua; Zhang, Zhihui; Fu, Dingliang; Zhang, Wanbin [Tetrahedron, 2011, vol. 67, # 12, p. 2246 - 2250]
[8]Matcha, Kiran; Antonchick, Andrey P. [European Journal of Organic Chemistry, 2019, vol. 2019, # 2, p. 309 - 312]

2
[ 108-24-7 ]
[ 3923-52-2 ]
[ 3848-49-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In dichloromethane for 16h; Reflux; Inert atmosphere;
72%	With dmap; triethylamine
	With sodium hydroxide; diethyl ether

	With sodium hydride In benzene
	With pyridine; dmap In dichloromethane at 0 - 20℃;
	With dmap; triethylamine In dichloromethane at 20℃;	2.1.1. 1,1-Dimethylpropargyl Acetate (B) General procedure: To a stirred solutionof compound a (5 ml, 51.28 mmol, 1 equiv.) in dryDCM(40 ml), triethyl amine (7.67 ml, 1.08 equiv.), acetic anhydride(6.0 ml, 1.15 equiv.), and DMAP (325 mg, 5 mol%) areadded sequentially at room temperature and stirred overnight(Scheme 1). After being monitored by TLC, the reactionmixture is diluted with saturated NH4Cl solution.Aqueous phase of the reaction mixture is extracted withDCM (2×25 ml). Organic phase obtained is washed with1 ml HCl twice and concentrated using vacuum, which givesthe crude compound, which is further puri?ed by ord b in 91% isolated yield (5.87 g).

Reference： [1]Lepronier, Aymeric; Achard, Thierry; Giordano, Laurent; Tenaglia, Alphonse; Buono, Gerard; Clavier, Herve [Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 631 - 642]
[2]Marion, Nicolas; Carlqvist, Peter; Gealageas, Ronan; De Fremont, Pierre; Maseras, Feliu; Nolan, Steven P. [Chemistry - A European Journal, 2007, vol. 13, # 22, p. 6437 - 6451]
[3]Cadiot [Annales de Chimie (Cachan, France), 1956, vol. <13> 1, p. 214,224]
[4]Hartzler,H.D. [Journal of the American Chemical Society, 1961, vol. 83, p. 4990 - 4996]
[5]Sabbasani, Venkata R.; Lee, Hyunjin; Xia, Yuanzhi; Lee, Daesung [Angewandte Chemie - International Edition, 2016, vol. 55, # 3, p. 1151 - 1155][Angew. Chem., 2015, vol. 128, # 3, p. 1163 - 1167,4]
[6]Alduhaish, Osamah; Varala, Ravi; Adil, Syed Farooq; Khan, Mujeeb; Siddiqui, Mohammed Rafiq H.; Alwarthan, Abdulrhman; Alam, M. Mujahid [Journal of Chemistry, 2020, vol. 2020]

3
[ 119-61-9 ]
[ 3923-52-2 ]
[ 1483-74-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; tetrabutylammomium bromide In toluene at 70℃; for 1h;
81%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: benzophenone In tetrahydrofuran; hexane at 20℃; for 22h;
81%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzophenone In tetrahydrofuran at 20℃; for 22h;

81%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: benzophenone In tetrahydrofuran; hexane at 20℃; for 22h;	1 General procedure for the synthesis of diols 2a-c General procedure: n-Butyllithium (2 eq, 3.85mL, 2.5M in hexane) was added dropwise to a solution of 1,1-diarylprop-2-yn-1-ol (1.00g; 4.8mmol) in dry THF (25mL) at 0°C and the cold mixture was maintained under constant stirring for 30min. The adequate benzophenone (1.1 eq) was added, at once, to the solution and the resulting mixture stirred at room temperature for 22h. The solvent was removed, HCl (5%, 30mL) was added and the aqueous phase was extracted with ethyl acetate (3×30mL). The combined organic phases were dried (Na2SO4) and the solvent removed under reduced pressure to give an oil which was purified by recrystallization from CH2Cl2/petroleum ether.
	With potassium hydroxide; N,N-dimethyl acetamide
	With 1-methyl-pyrrolidin-2-one; potassium hydroxide
	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzophenone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -78 - 20℃; for 14h;

Reference： [1]Dehmlow, Eckehard V.; Shamout, Abdul Rahman [Liebigs Annalen der Chemie, 1982, # 9, p. 1750 - 1752]
[2]Sousa, Ceu M.; Berthet, Jerome; Delbaere, Stephanie; Coelho, Paulo J. [Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 6956 - 6961]
[3]Sousa, Céu M.; Berthet, Jerome; Delbaere, Stephanie; Coelho, Paulo J. [European Journal of Organic Chemistry, 2018, vol. 2018, # 25, p. 3291 - 3297]
[4]Costa, Diogo; Sousa, Céu M.; Coelho, Paulo J. [Tetrahedron, 2018, vol. 74, # 51, p. 7372 - 7379]
[5]Chodkiewicz [Annales de Chimie (Cachan, France), 1957, vol. <13> 2, p. 819,861, 862]
[6]Chodkiewicz [Annales de Chimie (Cachan, France), 1957, vol. <13> 2, p. 819,861, 862]
[7]Xing, Junhao; Zhu, Yong; Lin, Xiao; Liu, Na; Shen, Yue; Lu, Tao; Dou, Xiaowei [Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1595 - 1599]

4
[ 3016-97-5 ]
[ 3923-52-2 ]
[ 15880-45-2 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 1849,1852

5
[ 3029-32-1 ]
[ 3923-52-2 ]
[ 122240-89-5 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 1223,1233

6
[ 39909-72-3 ]
[ 3923-52-2 ]
[ 40660-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrahydrofuran; diethyl ether; phenyllithium Behandeln des nach der Hydrolyse mit wss. HCl erhaltenen Reaktionsprodukts in Aether und THF mit SnCl₂ und HCl;

Reference： [1]Kuhn; Fischer [Chemische Berichte, 1959, vol. 92, p. 1849,1852]

7
[ 3923-52-2 ]
[ 1210-39-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid In 1,4-dioxane; water for 0.0833333h; Heating;
97%	With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate In water; ethyl acetate at 80℃; for 24h; Sealed tube; Green chemistry; chemoselective reaction;	General Procedure for ‘On-Water’ AlkyneHydration by Catalyst AgBAr^F Under Sealed Tube Conditions. General procedure: Calculated amount of AgBArF (97.1 mg, 0.1 mmol) was weighed into a long necked glass vessel, followed by addition of alkyne (1 mmol). 10 μL of EtOAc was added and stirred for 5 minutes. Internal standard n-dodecane (1 mmol) and 3 mL water was then added and the vessel was sealed under vacuum. The whole set-up was placed in an oil bath at 80 °C, stirred and heated for 12/24 hours. After the completion of reaction, the seal was broken and 3 mL EtOAc was added to it, stirred for 5 minutes and the organic layer was collected. The organic layer was passed through a very short column of silica to remove any impurities and subjected to GC-MS analysis. Products were purified by chromatography on a silica gel column using hexane/EtOAc as eluent. The isolated products were characterized by 1H and ESI-MSspectra.
96%	With ReOCl₃(SMe₂)(OPPh₃) In 1,2-dimethoxyethane at 80℃; for 20h;

95%	With trifluoroacetic acid In tetrahydrofuran for 0.166667h; Heating;
95%	With [Ag{μ²-N,S-(1,3,5-triaza-7-phosphaadamantane)=NP(=S)(OEt)₂}]_x[SbF₆]_x In water at 160℃; for 0.75h; Microwave irradiation;
94%	With [IrCp*(NCMe)₂(PPh₂Me)][hexafluorophosphate]₂ In dichloromethane-d2 at 20℃; for 2h; Inert atmosphere; Schlenk technique;
93%	With water In neat (no solvent) at 100℃; for 15h; Green chemistry;	General procedure for hydration of alkynes General procedure: Reactions were performed in a magnetically stirred round bot-tomed flask fitted with a condenser and placed in a temperature controlled oil bath. Zeolite (H) (100 mg) was added to the well stirred solution of alkyne (2 mmol) and H2O (8 mmol) and the reac-tion mixture was allowed to stir at 100 °C. After disappearance of the alkyne (monitored by TLC) or after an appropriate time, the reaction mixture was cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded residue. and it was further puri-fied by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products were identified on the basisof H1 and C13NMR spectral data.
91%	With indium(III) chloride In water at 160℃; for 0.0833333h; Microwave irradiation;
91%	With [Re(κ³-P,N,S-Ph₂PCH₂P{=NP(=S)(OPh)₂}Ph₂)(CO)₃]SbF₆ In tetrahydrofuran at 80℃; for 0.0833333h; Microwave irradiation; Inert atmosphere; regioselective reaction;
91%	With [Re(κ³-P,N,S-Ph₂PCH₂P{=NP(=S)(OPh)₂}Ph₂)(CO)₃]SbF₆ at 80℃; for 0.166667h; Inert atmosphere; Schlenk technique;
90%	With sulfuric acid In 1,4-dioxane for 2h; Reflux;
90%	With indium(III) triflate; water; toluene-4-sulfonic acid In 1,2-dichloro-ethane for 1h; Sealed tube; Reflux; regioselective reaction;	6.14 4.2 General procedure for the hydration of alkynes 1a-1n and 1p-1t General procedure: The reaction mixture of In(OTf)3 (11.2 mg, 2 mol %), PTSA (57.1 mg, 30 mol %), DCE (2.0 mL), alkynes 1a-1n or 1p-1t (1.0 mmol) and water (0.2 mL) in a 10 mL flask or in a 10 mL sealed tube was stirred at reflux and monitored periodically by TLC. Upon completion, DCE was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a-2n or 2p-2t.
90%	With Bi³⁺-montmorillonite In ethanol; acetonitrile at 80℃; for 1.5h;	10 example 10 The 1,1-diphenyl -2 propyn-1-ol (208 mg, 1mmol) dissolved in 10 ml of acetonitrile, adding Bi3+-montmorillonite (200 mg) and ethanol (7.5mmol, 0 . 44 ml), stirring and heating, in the 80 °C reaction under 1.5 hours, filtered to remove Bi3+-polynite, concentrated filtrate, concentrate column chromatography separation to obtain the product 3,3-diphenyl acrolein 187 mg, yield 90%;
90%	With N-methoxylamine hydrochloride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride In 1,2-dichloro-ethane at 90℃; for 0.0833333h;
90%	With phosphonic Acid In dichloromethane; water at 110℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;	Experimental section General procedure: Typical procedure: propargyl alcohols (0.2 mmol), H3PO3 50 wt% aqueous solution (0.3 mmol), CH2Cl2 (0.5 mL) were placed in10 mL sealed Schlenk tube under N2 atmosphere, then stirred at 110 C for 2 h and monitored by GC or GC-MS or TLC. After completionof the reaction, the mixture was cooled to room temperature, washed with saturated Na2CO3 solution, then extracted three times with CH2Cl2. The combined organic layer was dried with anhydrous Na2SO4, subjected to filtration, and concentrated in vacuo.The residue was purified by column chromatography on silica geland eluted with petroleum ether/ethyl acetate to afford the pure products.
89%	In acetone at 60℃; for 0.0833333h;
88%	With [CpRu{PhP(C₆H₄-o-S)2}RuCp](OTf)2; isopropyl alcohol In 1,2-dichloro-ethane at 60℃; for 2h;
85%	With iron(III) chloride hexahydrate In glycerol at 25℃; for 0.166667h;
84.5%	In water at 100℃; for 3h; Molecular sieve;	3 Example 3 Weigh 100 mg of 1,1,-diphenyl-2-propyn-1-ol and dissolve it by heating at 100 ° C. Add 80 μL of deionized water, stir for 10 minutes, and slowly add 8 mg of SBA-15 molecular sieve (5 minutes). After the addition), the Meyer-Schuster rearrangement reaction of the following reaction equation was carried out at a temperature of 100 °C:After reacting for 3 hours, 5 ml of chemically pure ethyl acetate was added to dissolve the organic matter, and then the molecular sieve was filtered off, and the ethyl acetate solution was filtered off with anhydrous sodium sulfate to remove a small amount of water, filtered, and dried, and then separated by column chromatography to obtain 84.5 mg of product. It is 3,3-diphenylpropenal in a yield of 84.5%.
83%	With methyl trifluoromethanesulfonate In acetonitrile at 70℃; for 1h;	Methyl Triflate Catalyzed Meyer-Schuster Rearrangement; Cinnamaldehyde (2a); Typical Procedure General procedure: To a 25 mL round-bottomed flask were added 1-phenylprop-2-yn-1-ol (1a; 40 mg, 0.3 mmol), TFE (0.5 mL), and MeOTf (6 μL, 0.06 mmol, 0.2 equiv). Then the flask was immersed in a 70 °C preheated oil bathand the mixture was stirred for 1 h. After completion, the solution was removed and the residue was subject to flash chromatography (silica gel) with PE/EtOAc as eluent to afford the desired rearrangement product.
83%	With water; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	3.2. Typical Procedure for the Preparation of α,β-Unsaturated Aldehydes 3 from the Corresponding ArylPropargyl Alcohols 2 General procedure: Freshly distilled Tf2O (169 μL, 1.0 mmol) was addedslowly to a solution of Ph3PO (556 mg, 2.0 mmol) in CH2Cl2(10 mL) at 0oC under a N2 atmosphere. After stirring for 10min, the propargyl alcohol 2 (1.0 mmol) was added as aCH2Cl2 solution (2 mL), followed by the addition water (36μL, 2.0 mmol), Et3N (280 μL, 2.0 mmol) and further stirringat r.t. for 1h. The mixture was diluted with CH2Cl2 (10 mL)and washed with 5% NaHCO3 (20 mL), and brine (20 mL).The organic layer was dried (Na2SO4), and the residue waspurified (silica gel, 5-10% EtOAc-hexanes) to afford thealdehydes 3 (Table 1).
82%	With silver hexafluoroantimonate; water In methanol at 75℃; for 24h; chemoselective reaction;
79%	With benzoic acid In toluene 1.) 70 deg C, 2 h, 2.) 100 deg C, 32 h;
64%	With iron(III) chloride In tetrahydrofuran for 10h; Reflux;
	With sulfuric acid
	Multi-step reaction with 2 steps 1: 99 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C 2: 46 percent / TMSOTf / tetrahydrofuran / 3 h / -78 - 20 °C
	With hydrogenchloride In ethanol; water at 60℃; for 24h;	1.2 The oil containing 1, 1-diphenyl-2-propyn-1-ol (20 g) from Step 1 was dissolved in 100 mL ethanol in a reaction flask. A few drops of concentrated hydrochloric acid were added to the solution. The solution was heated at 60° C for 24 hours and was poured into an ice/water mixture and extracted with ether. The solvent was evaporated under vacuum to yield a red-colored gum that was flash column separated on alumina with hexane/ethyl acetate in a 80: 20 volume ratio, and recrystallized from dichloromethane/hexane in a 80: 20 volume ratio to give 16.5 g of a product. NMR analysis showed the product to have a structure consistent with B- phenylcinnamaldehyde.

Reference： [1]Teral, Yannick; Roubaud, Gabriel; Aubert, Claude; Faure, Robert; Campredon, Mylene [Australian Journal of Chemistry, 2005, vol. 58, # 7, p. 517 - 521]
[2]Saha, Sayantani; Sarbajna, Abir; Bera, Jitendra K. [Tetrahedron Letters, 2014, vol. 55, # 8, p. 1444 - 1447]
[3]Location in patent: experimental part Stefanoni, Massimo; Luparia, Marco; Porta, Alessio; Zanoni, Giuseppe; Vidari, Giovanni [Chemistry - A European Journal, 2009, vol. 15, # 16, p. 3940 - 3944]
[4]Cadierno, Victorio; Garcia-Garrido, Sergio E.; Gimeno, Jose [Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 101 - 110]
[5]Garcia-Alvarez, Joaquin; Diez, Josefina; Vidal, Cristian; Vicent, Cristian [Inorganic Chemistry, 2013, vol. 52, # 11, p. 6533 - 6542]
[6]Talavera, María; Bravo, Jorge; Gonsalvi, Luca; Peruzzini, Maurizio; Zuccaccia, Cristiano; Bolaño, Sandra [European Journal of Inorganic Chemistry, 2014, vol. 2014, # 36, p. 6268 - 6274]
[7]Mameda, Naresh; Peraka, Swamy; Marri, Mahender Reddy; Kodumuri, Srujana; Chevella, Durgaiah; Gutta, Naresh; Nama, Narender [Applied Catalysis A: General, 2015, vol. 505, p. 213 - 216]
[8]Location in patent: experimental part Cadierno, Victorio; Francos, Javier; Gimeno, José [Tetrahedron Letters, 2009, vol. 50, # 33, p. 4773 - 4776]
[9]Garcia-Alvarez, Joaquin; Diez, Josefina; Gimeno, Jose; Seifried, Christine M. [Chemical Communications, 2011, vol. 47, # 22, p. 6470 - 6472]
[10]Garcia-Alvarez, Joaquin; Diez, Josefina; Gimeno, Jose; Seifried, Christine M.; Vidal, Cristian [Inorganic Chemistry, 2013, vol. 52, # 9, p. 5428 - 5437]
[11]Zhou, Yibo; Trewyn, Brian G.; Angelici, Robert J.; Woo, L. Keith [Journal of the American Chemical Society, 2009, vol. 131, # 33, p. 11734 - 11743]
[12]Gao, Qi; Li, Shenyan; Pan, Yingming; Xu, Yanli; Wang, Hengshan [Tetrahedron, 2013, vol. 69, # 19, p. 3775 - 3781]
[13]Current Patent Assignee: SHAANXI NORMAL UNIVERSITY - CN105503553, 2016, A Location in patent: Paragraph 0103; 0104; 0105; 0106; 0107; 0108; 0109; 0110
[14]Zhang, Qi; Zhang, Linjing; Tang, Chaojun; Luo, Huan; Cai, Xuediao; Chai, Yonghai [Tetrahedron, 2016, vol. 72, # 44, p. 6935 - 6942]
[15]Gan, Xiaotang; Fu, Zuqi; Liu; Yan, Yani; Chen, Chao; Zhou, Yongbo; Dong, Jianyu [Tetrahedron Letters, 2019, vol. 60, # 32]
[16]Bustelo, Emilio; Dixneuf, Pierreh H. [Advanced Synthesis and Catalysis, 2007, vol. 349, # 6, p. 933 - 942]
[17]Location in patent: experimental part Yuki, Masahiro; Miyake, Yoshihiro; Nishibayashi, Yoshiaki [Organometallics, 2010, vol. 29, # 22, p. 5994 - 6001]
[18]Ríos-Lombardía, Nicolás; Cicco, Luciana; Yamamoto, Kota; Hernández-Fernández, José A.; Morís, Francisco; Capriati, Vito; García-Álvarez, Joaquín; González-Sabín, Javier [Chemical Communications, 2020, vol. 56, # 96, p. 15165 - 15168]
[19]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN110078611, 2019, A Location in patent: Paragraph 0026-0031
[20]Yang, Lu; Zeng, Qingle [Synthesis, 2017, vol. 49, # 14, p. 3149 - 3156]
[21]Moussa, Ziad; Aljuhani, Ateyatallah [Letters in Organic Chemistry, 2018, vol. 15, # 10, p. 845 - 853]
[22]Thuong, Mathieu Bui The; Mann, Andre; Wagner, Alain [Chemical Communications, 2012, vol. 48, # 3, p. 434 - 436]
[23]Picquet, Michel; Bruneau, Christian; Dixneuf, Pierre H. [Chemical Communications, 1997, # 13, p. 1201 - 1202]
[24]Location in patent: experimental part El Douhaibi, Ahmad Samih; Judeh, Zaher M. A.; Basri, Hedaya; Moussa, Ziad; Messali, Mouslim; Qi, Gao [Synthetic Communications, 2011, vol. 41, # 4, p. 533 - 540]
[25]Hennion; Fleck [Journal of the American Chemical Society, 1955, vol. 77, p. 3253,3257]
[26]Ishikawa; Okano; Aikawa; Saito [Journal of Organic Chemistry, 2001, vol. 66, # 13, p. 4635 - 4642]
[27]Current Patent Assignee: ESSILORLUXOTTICA - WO2005/61514, 2005, A1 Location in patent: Page/Page column 40-41

8
[ 3923-52-2 ]
[ 71228-76-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium hydroxide; potassium hypobromite In pentane for 72h; Ambient temperature;
87%	With potassium fluoride; N-Bromosuccinimide; silver nitrate In water; acetonitrile at 20℃; for 20h; Inert atmosphere; Schlenk technique; Darkness;	3-Bromo-1,1-diphenylprop-2-yn-1-ol (5) 1,1-Diphenylprop-2-yn-1-ol (2, 1.00 g, 4.80 mmol) was dissolved in acetonitrile (30 mL) with an addition of water (0.220 mL, 12.2 mmol). The flask was wrapped with aluminum foil and NBS (1.04 g, 5.84 mmol), AgNO3 (0.245 g, 1.44 mmol), and KF (0.167 g, 2.87 mmol) were added. The mixture was stirred for 20 h. After this time solvent was removed on rotary evaporator. Mixture of DCM/hexane (v/v, 1/1) was poured onto greasy residual and this mixture was passed through a short (10 cm) silica gel plug. 5 (1.203 g, 4.19 mmol, yield 87%) was obtained as beige solid. 1H NMR (500 MHz, CDCl3) δ 7.60- 7.56 (m, 4H), 7.37 - 7.32 (m, 4H), 7.31 - 7.27 (m, 2H), 2.80 (s, 1H). 13C NMR (126 MHz, CDCl3) δ 144.5, 128.5,128.1, 126.2, 82.8, 75.6, 48.4.
	With sodium hypobromide

	With sodium hypobromide
	With bromine; potassium hydroxide In diethyl ether; water at 0 - 20℃;
	With N-Bromosuccinimide; silver nitrate In acetone at 0 - 20℃; for 2h; Darkness; Inert atmosphere;
	Stage #1: 1,1-diphenyl-2-propyn-1-ol With bromine; potassium hydroxide In water Inert atmosphere; Stage #2: With N-Bromosuccinimide; silver nitrate In acetone Inert atmosphere;

Reference： [1]Saalfrank, Rolf W.; Welch, Andreas; Haubner, Martin; Bauer, Udo [Liebigs Annalen, 1996, # 2, p. 171 - 181]
[2]Gulia, Nurbey; Pigulski, Bartłomiej; Szafert, Sławomir [Arkivoc, 2017, vol. 2017, # 3, p. 191 - 204]
[3]Chodkiewicz [Annales de Chimie (Cachan, France), 1957, vol. <13> 2, p. 819,861, 862]
[4]Greaves,P.M. et al. [Journal of the Chemical Society C: Organic, 1971, p. 667 - 670]
[5]Shemyakina, Olesya A.; Volostnykh, Ol'ga G.; Stepanov, Anton V.; Ushakov, Igor' A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 42, p. 7117 - 7121]
[6]Ghorai, Sourav; Lee, Daesung [Organic Letters, 2021, vol. 23, # 3, p. 697 - 701]
[7]Wei, Yunlong; Wu, Xinxin; Zhang, Hong; Zhu, Chen [Angewandte Chemie - International Edition, 2021, vol. 60, # 37, p. 20215 - 20219][Angew. Chem., 2021, vol. 133, # 37, p. 20377 - 20381]

9
[ 67-56-1 ]
[ 3923-52-2 ]
[ 13632-79-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrafluoroboric acid In water; acetone at 30℃; for 24h; regioselective reaction;
58%	With C₄₄H₄₀Cl₂NPRuS₂ at 90℃;
21%	With ferrocenium hexafluorophosphate In dichloromethane at 40℃; for 5h; Sealed tube;	General Procedure for the etherification of 1,1-diphenylprop-2-yn-1-ol General procedure: (1-methoxy-2-propyn-1-ylidene)bis-Benzene (Table 2, entry 9)[17] 1,1-diphenyl-2-propyn-3-ol (0.102 g, 0.491 mmol) was addedto a 5 mL screw cap vial and dissolved in CH2Cl2(1 mL). Methanol(0.016 g, 0.497 mmol) was then added followed by [Fc]PF6(0.005 g,0.014 mmol). The vial was then sealed and heated to 40C for 5 h.The solvent was removed and the residue was chromatographedon a silica gel column (2.5 × 30 cm, 2:1 v/v hexanes/CH2Cl2) togive the product 8 as a yellow oil (0.022 g, 0.099 mmol, 21%).

With sulfuric acid Ambient temperature;

Reference： [1]Barreiro, Elena; Sanz-Vidal, Alvaro; Tan, Eric; Lau, Shing-Hing; Sheppard, Tom D.; Dez-Gonzlez, Silvia [European Journal of Organic Chemistry, 2015, vol. 2015, # 34, p. 7544 - 7549]
[2]Location in patent: scheme or table Costin, Stephen; Sedinkin, Sergey L.; Bauer, Eike B. [Tetrahedron Letters, 2009, vol. 50, # 8, p. 922 - 925]
[3]Queensen, Matthew J.; Rabus, Jordan M.; Bauer, Eike B. [Journal of Molecular Catalysis A: Chemical, 2015, vol. 407, p. 221 - 229]
[4]Libman,N.M.; Kuznetsov,S.G. [Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1451 - 1455][Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 8, p. 1494 - 1499]

10
[ 119-61-9 ]
[ 74-86-2 ]
[ 3923-52-2 ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With sodium ethanolate In ethanol at 0 - 5℃; for 0.5h; Inert atmosphere; Large scale;	4 Example 1. Preparation of methylbutynol General procedure: In a 10 L three-necked flask, 6 L of anhydrous methanol was added, and the mixture was shielded with nitrogen. Under cooling with ice water, 550 g of sodium metal (small) was slowly added.After all the sodium metal was dissolved, 1.5 L of acetone was added, and the mixture was uniformly stirred and cooled to below 0 °C. Slowly pass acetylene, The flow rate of the acetylene is controlled so that the reaction temperature is 0 to 5 °C. When the reaction is no longer exothermic, the reaction is complete. Then, a small amount of acetylene was introduced, and the closed micro-positive pressure (nitrogen balloon was not changed) was reacted for 0.5 hour. In another 20 L three-necked flask, 2.5 kg of ammonium chloride and 3 L of methanol were added.Under ice cooling, the reaction solution was poured into an ammonium chloride system to carry out a neutralization reaction. The neutralization reaction temperature was controlled to be less than 20 °C. After the neutralization is completed, it is filtered. The filtrate was first distilled with methanol, methanol was applied, and then the product methylbutynol was distilled under reduced pressure to obtain 1.69 kg. The product purity was 99.5%, and the yield was 99.1%.
96%	Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃;
90%	With sodium hydroxide; tetrabutylammomium bromide In toluene for 2h; Ambient temperature;

	With ammonia; lithium In diethyl ether; ammonia
	(i) Li, liq. NH₃, (ii) /BRN= 1238185/; Multistep reaction;
	With ammonia; lithium 1.) -78 deg C, 2.) ether; Yield given. Multistep reaction;
59.5 g	With ammonia; sodium In diethyl ether for 7h;
	Stage #1: acetylene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
	Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
	Stage #1: acetylene With ethylmagnesium bromide In tetrahydrofuran at 0 - 25℃; for 1.16667h; Stage #2: benzophenone In tetrahydrofuran at 23 - 25℃; for 5h;
	With potassium <i>tert</i>-butylate In neat (no solvent) at 25℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: PANJIN GELIN KAIMO TECH - CN108863717, 2018, A Location in patent: Paragraph 0036; 0037; 0038; 0043; 0044; 0045; 0046
[2]Kuwatani, Yoshiyuki; Yamamoto, Gaku; Oda, Masaji; Iyoda, Masahiko [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 12, p. 2188 - 2208]
[3]Dehmlow, Eckehard V.; Shamout, Abdul Rahman [Liebigs Annalen der Chemie, 1982, # 9, p. 1750 - 1752]
[4]Hartzler,H.D. [Journal of the American Chemical Society, 1961, vol. 83, p. 4990 - 4996]
[5]Ried,W.; Neidhardt,R. [Chemische Berichte, 1970, vol. 103, p. 2208 - 2224]
[6]Yakhontov; Kutina; Shishkin; Zhikhareva; Vysochin; Vorob'eva; Kaminka; Shevchenko; Mashkovskii [Pharmaceutical Chemistry Journal, 1989, vol. 23, # 1, p. 24 - 30]
[7]Gaspar, Peter P.; Whitsel, Bonnie L.; Jones, Maitland; Lambert, Joseph B. [Journal of the American Chemical Society, 1980, vol. 102, # 19, p. 6108 - 6113]
[8]Zhang, Xiaoxiang; Teo, Wan Teng; Sally; Chan, Philip Wai Hong [Journal of Organic Chemistry, 2010, vol. 75, # 18, p. 6290 - 6293]
[9]Zhang, Xiaoxiang; Teo, Wan Teng; Chan, Philip Wai Hong [Journal of Organometallic Chemistry, 2011, vol. 696, # 1, p. 331 - 337]
[10]Wang, Jia; Zhu, Hai-Tao; Li, Ying-Xiu; Wang, Li-Jing; Qiu, Yi-Feng; Qiu, Zi-Hang; Zhong, Mei-Jin; Liu, Xue-Yuan; Liang, Yong-Min [Organic Letters, 2014, vol. 16, # 8, p. 2236 - 2239]
[11]Yaragorla, Srinivasarao; Latha, Dandugula Sneha; Rajesh, Pallava [Advanced Synthesis and Catalysis, 2021, vol. 363, # 24, p. 5486 - 5492]

11
[ 90-15-3 ]
[ 3923-52-2 ]
[ 856-94-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With fipronilβ-cyclodextrin In water at 60℃; for 5h; Green chemistry; regioselective reaction;
60%	With montmorillonite K-10 In toluene at 20℃; for 2h;
21%	With toluene-4-sulfonic acid In toluene for 6h; Heating;

With para-dodecylbenzenesulfonic acid In toluene at 80℃; for 2h;

2 Example 2 Using 1,1-diphenyl-2-propyn-1-ol and 1-naphthol as raw materials, dodecylbenzenesulfonic acid as catalyst, mobile phase as toluene, the mass fraction of mobile phase containing reaction raw materials is 40% , the mass fraction of mobile phase containing catalyst is 5‰. After pre-adjusting the temperature of the above mobile phase system to 80 °C, the constant-flow pump was used to control the rate at which the molar ratio of the reactant raw material and the catalyst was 1:1:0.05, and were injected into the microchannel reactor for mixing, and the reaction was carried out at 80 °C for 2 h. , to obtain a solution containing the target photovariable dye, and the reaction formula is shown below. The solution was concentrated, recrystallized, decolorized and dried to obtain a white powder product. The melting point of the product is 150-152°C , and the nuclear magnetic resonance spectrum shows that the obtained product has a structure conforming to 2,2-diphenyl-2H-naphtho[1,2-b]pyran.

Reference： [1]Ghatak, Avishek; Khan, Sagar; Bhar, Sanjay [Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 435 - 443]
[2]Hosseinzadeh, Rahman; Mohadjerani, Maryam; Javad Ardestanian, Mohammad; Naimi-Jamal, Mohammad Reza; Lasemi, Zahra [Journal of Chemical Sciences, 2014, vol. 126, # 4, p. 1081 - 1089]
[3]Pozzo, Jean-Luc; Samat, Andre; Guglielmetti, Robert; Dubest, Roger; Aubard, Jean [Helvetica Chimica Acta, 1997, vol. 80, # 3, p. 725 - 738]
[4]Van Gemert; Bergomi; Knowles [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 246, p. 67 - 73]
[5]Current Patent Assignee: GUANGZHOU COLORBLOOMING TECH - CN113943267, 2022, A Location in patent: Paragraph 0031-0033

12
[ 23596-81-8 ]
[ 3923-52-2 ]
[ 120474-80-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine Heating;
73%	With copper(l) iodide; triethylamine at 85℃; for 2.5h;
73%	With copper(l) iodide; triethylamine at 85℃; for 2h;

Reference： [1]Toda, Fumio; Tanaka, Koichi; Sano, Isao; Isozaki, Toru [Angewandte Chemie, 1994, vol. 106, # 17, p. 1856 - 1858]
[2]Iyoda, Masahiko; Kuwatami, Yoshiyuki; Oda, Masaji [Journal of the American Chemical Society, 1989, vol. 111, # 10, p. 3761 - 3762]
[3]Kuwatani, Yoshiyuki; Yamamoto, Gaku; Oda, Masaji; Iyoda, Masahiko [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 12, p. 2188 - 2208]

13
[ 3923-52-2 ]
[ 135-19-3 ]
[ 4222-20-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 1,1-diphenyl-2-propyn-1-ol (20.8 grams, 0.1 mole) was added to a reaction flask containing 200 milliliters of benzene and 15 grams of 2-naphthol. The reaction mixture was warmed to 55° C. and after all of the 2-naphthol was dissolved, 0.25 grams of p-toluenesulfonic acid was added to the stirred reaction mixture. The mixture changed from light tan to dark black, became exothermic, and the temperature rose to 70° C. After a few minutes, the reaction mixture lightened and began to cool. After 30 minutes, the reaction mixture was poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was washed once with 10 percent aqueous sodium hydroxide and then washed with water. The solvent, benzene, was removed on a rotary evaporator. The resulting light tan solid residue was slurried with 100 milliliters of hexane and filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[2,1-b]pyran. The solid product had a melting point of 156°-158° C. and was 98 percent pure as determined by liquid chromatographic analysis.
98%	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 1,1-diphenyl-2-propyn-1-ol (20.8 grams, 0.1 mole) was added to a reaction flask containing 200 milliliters of benzene and 15 grams of 2-naphthol. The reaction mixture was warmed to 55° C. and after all of the 2-naphthol was dissolved, 0.25 gram of p-toluenesulfonic acid was added. The mixture changed from light tan to dark black in color and the temperature rose to 70° C. After a few minutes, the reaction mixture became lighter in color and began to cool. Thirty minutes later, the contents of the flask were poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic layer was separated, washed once with 10 percent aqueous sodium hydroxide, and then washed with water. The benzene solvent was removed on a rotary evaporator and the resulting light tan residue was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[2,1-b]pyran. The solid product had a melting point of 156° to 158° C. and was 98 percent pure as determined by liquid chromatographic analysis.
98%	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.2 COMPARATIVE EXAMPLE 2 COMPARATIVE EXAMPLE 2 1,1-diphenyl-2-propyn-1-ol (20.8 grams, 0.1 mole) was added to a reaction flask containing 200 milliliters of benzene and 15 grams of 2-naphthol. The reaction mixture was warmed to 55° C. and after all of the 2-naphthol was dissolved, 0.25 grams of p-toluenesulfonic acid was added. The mixture changed from light tan to dark black and the temperature rose to 70° C. After a few minutes, the reaction mixture lightened and began to cool. Thirty minutes later, the contents of the flask were poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was separated, washed once with 10 percent aqueous sodium hydroxide, and then washed with water. Benzene was removed on a rotary evaporator and the resulting light tan solid residue was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[ 2,1-b]pyran. The solid product had a melting point of 156°-158° C. and was 98 percent pure, as determined by liquid chromatographic analysis.

98%	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 1,1-diphenyl-2-propyn-1-ol (20.8 grams, 0.1 mole) was added to a reaction flask containing 200 milliliters of benzene and 15 grams of 2-naphthol. The reaction mixture was warmed to 55° C. and after all of the 2-naphthol was dissolved, 0.25 gram of p-toluenesulfonic acid was added. The mixture changed from light tan to dark black in color and the temperature rose to 70° C. After a few minutes, the reaction mixture became lighter in color and began to cool. Thirty minutes later, the contents of the flask were poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was separated, washed once with 10 percent aqueous sodium hydroxide, and then washed with water. The benzene solvent was removed on a rotary evaporator and the resulting light tan solid residue was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho [2,1-b]pyran. The solid product had a melting point of 156°-158° C. and was 98 percent pure as determined by liquid chromatographic analysis.
97%	With montmorillonite K-10 In toluene at 20℃; for 0.75h;
92%	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Heating;
88%	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane
75%	With toluene-4-sulfonic acid In toluene for 2h; Reflux;	4.2. Preparation of 3,3-diaryl-3H-naphtho[2,1-b]pyrans (4), general procedure General procedure: Preparation methods of 3,3-diaryl-3H-naphtho[2,1-b]pyrans were generally based on condensation reactions taking place in the apolar solvent as toluene under acid catalysis, which starting from suitable naphthols and propargyl alcohols.[26], [27] and [28]The propargyl alcohol (2) was prepared from the diaryl ketone (1) as outlined in Scheme 1. 10 mmol diaryl ketone (1) was dissolved in 50 mL dry THF and was added dropwise to a solution of 50 mmol sodium acetylide in THF below 0 °C. The mixture was then allowed to stir at room temperature for about 3 h until none of the diaryl ketone (1) remained by TLC examination of the reaction mixture. The reaction mixture was poured into iced water for separation. The organic phase was collected and followed by washing with water (3×50 mL) and then dried (anhyd Na2SO4). The propargyl alcohol was then obtained in the yield of about 80% after the short flash chromatography and was used for subsequent procedure directly.273 mmol propargyl alcohol (2), 3 mmol 2-naphthol derivative (3), and 1.0 g p-toluenesulfonic acid (TsOH) were dissolved in 50 mL toluene. The reaction mixture was refluxed for about 2 h until TLC examination indicated that none of the propargyl alcohol remained. The mixture was cooled to room temperature and washed with 1 mol L-1 NaOH solution (2×50 mL) and water. After drying with anhyd Na2SO4, removal of the toluene by vacuum evaporation gave a dark gum. The pure naphthopyran product was obtained by elution from silica using 10% ethyl acetate/hexane.
69%	With benzoic acid; 3,5-bis-trifluromethylphenylboronic acid In n-heptane at 80℃; for 17h; Sealed tube;
67%	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Reflux;
62%	With toluene-4-sulfonic acid In dichloromethane Heating;
62%	With toluene-4-sulfonic acid In toluene for 2h; Heating;
62%	With sodium hydroxide In toluene	C.1 Comparative Example 1 Comparative Example 1 3,3-Diphenyl[3H]naphtho[2,1-b]pyran is prepared in the following way: 10 mmol of 1,1-diphenyl-2-propyn-1-ol and 11 mmol of 2-naphthol are dissolved in warm anhydrous toluene (20 ml). A catalytic amount of para-toluene sulfonic acid is added. The mixture is refluxed under argon for 2 h 30 minutes. It is allowed to cool to room temperature and 20 ml of aqueous 5% NaOH solution are added. The aqueous phase is extracted continuously with methylene chloride. The organic phases are combined and dried over magnesium sulfate. The solvent is evaporated off under reduced pressure. The resulting product is purified by washing with hexane. Yield: 62% Empirical formula: C24H18O Molar mass: 334.42 g Melting point: 158° C.
62%	With pyridinium p-toluenesulfonate In 1,2-dichloro-ethane
56%	With silica gel; toluene-4-sulfonic acid at 20℃; for 1.16667h;
	With toluene-4-sulfonic acid In hexane; benzene	1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 To a 500 milliliter reaction flask were added 0.1 mole (20.8 grams) of 1,1-diphenyl-2-propyn-1-ol, 15 grams of 2-naphthol and 200 milliliters of benzene. The reaction mixture was warmed to 55°C. to dissolve all of the naphthol reactant. When all of the 2-naphthol was dissolved, 0.25 grams of p-toluene sulfonic acid was added to the stirred reaction mixture, which then changed from light tan to dark black and exothermed to 70°C. After a few minutes, the reaction mixture lightened and began to cool. After 30 minutes, the reaction mixture was poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was washed once with 10 percent aqueous sodium hydroxide and then washed with water. The benzene solvent was removed on a rotary evaporator. The resulting solid residue was a light tan solid, which was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[2,1-b]pyran, which was found to be 98 percent pure by HPLC. The product had a melting point range of 156-158°C.
	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 To a 500 milliliter reaction flask were added 0.1 mole of 1,1-diphenyl-2-propyn-1-ol (20.8 grams), 2-naphthol (515 grams) and 200 milliliters of benzene. The reaction mixture was warmed to 55° C. to dissolve all of the naphthol reactant. After all of the 2-naphthol was dissolved, 0.25 grams of p-toluene sulfonic acid was added to the stirred reaction mixture, which then changed from light tan to dark black and exothermed to 70° C. A few minutes later, the reaction mixture lightened and began to cool. After 30 minutes, the reaction mixture was poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was washed once with 10 percent aqueous sodium hydroxide and then washed with water. The benzene solvent was removed on a rotary evaporator. The resulting solid residue was a light tan solid, which was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[2,1-b]pyran, which was found to be 98 percent pure by liquid chromatographic analysis. The product had a melting point range of 156°-158° C.
	With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	C.1 COMPARATIVE EXAMPLE 1 COMPARATIVE EXAMPLE 1 To a 500 milliliter reaction flask were added 0.1 mole (20.8 grams) of 1,1-diphenyl-2-propyn-1-ol, 15 grams of 2-naphthol and 200 milliliters of benzene. The reaction mixture was warmed to 55° C. to dissolve all of the naphthol reactant. When all of the 2-naphthol was dissolved, 0.25 grams of p-toluene sulfonic acid was added to the stirred reaction mixture, which then changed from light tan to dark black and exothermed to 70° C. After a few minutes, the reaction mixture lightened and began to cool. After 30 minutes, the reaction mixture was poured into 100 milliliters of 10 percent aqueous sodium hydroxide and shaken. The organic phase was washed once with 10 percent aqueous sodium hydroxide and then washed with water. The benzene solvent was removed on a rotary evaporator. The resulting solid residue was a light tan solid, which was slurried with 100 milliliters of hexane and then filtered. The filtered solid was washed again with 100 milliliters of hexane and dried to provide 18.4 grams of the product, 3,3-diphenyl-3H-naphtho[2,1-b]pyran, which was found to be 98 percent pure by HPLC. The product had a melting point range of 156-158° C.
	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane
	With toluene-4-sulfonic acid In toluene at 50 - 60℃;	Naphthopyrans I and II were obtained using 2-naphthol and 1,1-diphenyl-2-propyn-1-ol or 1,1-(4,4′ -dimethoxyphenyl)-2-propyn-1-ol,respectively, by heating 2-naphthol with a propynol in toluene at 50-60o in the presence of toluene sulfonic acid as a catalyst. NaphthopyranIII was synthesized according to a similar procedure, but using 2-anthrolas a substrate. Propargyl alcohols were obtained from benzophenoneand 4,4′-dimethoxybenzophenone by procedures commonly used forreactions of this type. Thus, 1,1-(4,4′ -dimethoxyphenyl)-2-propyn-1-olwas isolated from the reaction of 4,4′ -dimethoxybenzophenone with theethylenediamine complex of lithium acetylide in anhydrous dimethylsulfoxide. 1,1-Diphenyl-2-propyn-1-ol was a commercial chemical.

Reference： [1]Current Patent Assignee: PPG INDUSTRIES INC - US5384077, 1995, A
[2]Current Patent Assignee: PPG INDUSTRIES INC - US5451344, 1995, A
[3]Current Patent Assignee: PPG INDUSTRIES INC - US5466398, 1995, A
[4]Current Patent Assignee: ESSILORLUXOTTICA - US5429774, 1995, A
[5]Hosseinzadeh, Rahman; Mohadjerani, Maryam; Javad Ardestanian, Mohammad; Naimi-Jamal, Mohammad Reza; Lasemi, Zahra [Journal of Chemical Sciences, 2014, vol. 126, # 4, p. 1081 - 1089]
[6]Zhao, Weili; Carreira, Erick M. [Organic Letters, 2003, vol. 5, # 22, p. 4153 - 4154]
[7]Location in patent: experimental part Guo, Kunpeng; Chen, Yi [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 62 - 71]
[8]Location in patent: experimental part Wang, Zhen; Meng, Qinghua; Zhang, Zhihui; Fu, Dingliang; Zhang, Wanbin [Tetrahedron, 2011, vol. 67, # 12, p. 2246 - 2250]
[9]Dimakos, Victoria; Singh, Tishaan; Taylor, Mark S. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 28, p. 6703 - 6711]
[10]Location in patent: experimental part Crossley, Daniel L.; Gabbutt, Christopher D.; Mark Heron; Kay, Paul; Mogstad, Martin [Dyes and Pigments, 2012, vol. 95, # 1, p. 62 - 68] Location in patent: experimental part Blackwell, Catherine J.; Gabbutt, Christopher D.; Guthrie, James T.; Heron, B. Mark [Dyes and Pigments, 2012, vol. 95, # 2, p. 408 - 420]
[11]Harie, Guenaelle; Samat, Andre; Guglielmetti, Robert; De Keukeleire, Denis; Saeyens, Wim; Van Parys, Inge [Tetrahedron Letters, 1997, vol. 38, # 17, p. 3075 - 3078]
[12]Pozzo, Jean-Luc; Samat, Andre; Guglielmetti, Robert; Dubest, Roger; Aubard, Jean [Helvetica Chimica Acta, 1997, vol. 80, # 3, p. 725 - 738]
[13]Current Patent Assignee: ESSILORLUXOTTICA - US6312811, 2001, B1
[14]Sahoo, Priyaranjan; Prakash, Kunal; Kumar, Satish [Supramolecular Chemistry, 2017, vol. 29, # 3, p. 183 - 192]
[15]Tanaka, Koichi; Aoki, Hiroko; Hosomi, Hiroyuki; Ohba, Shigeru [Organic Letters, 2000, vol. 2, # 14, p. 2133 - 2134]
[16]Van Gemert; Bergomi; Knowles [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 246, p. 67 - 73]
[17]Delbaere, Stephanie; Teral, Yannick; Bochu, Christophe; Campredon, Mylene; Vermeersch, Gaston [Magnetic Resonance in Chemistry, 1999, vol. 37, # 2, p. 159 - 162]
[18]Current Patent Assignee: PPG INDUSTRIES INC - EP613475, 1998, B1
[19]Current Patent Assignee: PPG INDUSTRIES INC - US5274132, 1993, A
[20]Current Patent Assignee: PPG INDUSTRIES INC - US5066818, 1991, A
[21]Location in patent: experimental part Kahle, Ingolf; Troeber, Oliver; Trentsch, Sabine; Richter, Hannes; Gruenler, Bernd; Hemeltjen, Steffen; Schlesinger, Maik; Mehring, Michael; Spange, Stefan [Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 5083 - 5088]
[22]Barachevsky, Valery А.; Gorelik, Alexander М.; Kobeleva, Оlga I.; Valova, Тatyana М.; Venidiktova, Оlga V. [Dyes and Pigments, 2021, vol. 184]

14
[ 3923-52-2 ]
[ 3923-51-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In ethanol
89%	With ammonia borane; copper(II) choride dihydrate In tetrahydrofuran; water at 60℃; diastereoselective reaction;
	With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Ambient temperature;

	With hydrogen In methanol at 20℃; for 0.0183333h; Inert atmosphere; Schlenk technique; Green chemistry;	2.3 Catalytic reactions under continuous flow General procedure: In a typical experiment, a deaereated solution of alkyne in methanol (0.1M) was allowed to flow through the PdMonoBor column catalyst (29mg, reactor volume 176 μL) at 0.2mLmin-1 together with a H2 flow of 1.3mLmin-1 at r.t. This resulted in a H2 pressure at the reactor inlet of ca. 1.2bar (corresponding to a H2/alkyne molar ratio of ca. 2.8), while the hydrogen gas was released at atmospheric pressure at the outlet of the reactor. Therefore, the pressure drop generated by monolithic reactor was ca. 0.2bar. The attainment of the steady-state conditions (ca. 1h) was taken as the reaction start time. The reaction was typically monitored for 14h time-on-stream by periodically analyzing the product solution for conversion and selectivity by GC, while 5.0mL aliquots were sampled at 1h intervals for Pd leaching determination by ICP-OES. The amount of Pd in solution was below the detection limit in each sample (0.006ppm).
	With hydrogen In toluene at 139.84℃; Flow reactor;
90 %Spectr.	With formic acid; triethanolamine; palladium dichloride In N,N-dimethyl-formamide at 30℃; for 24h; Inert atmosphere;
	With piperazine; hydrogen In ethanol at 100℃; for 23h; Green chemistry;
85 %Chromat.	With hydrogen In ethanol at 100℃; for 24h; chemoselective reaction;
	With hydrogen In toluene at 49.84℃;

Reference： [1]Yakhontov; Kutina; Shishkin; Zhikhareva; Vysochin; Vorob'eva; Kaminka; Shevchenko; Mashkovskii [Pharmaceutical Chemistry Journal, 1989, vol. 23, # 1, p. 24 - 30]
[2]Grela, Karol; Kusy, Rafał [Green Chemistry, 2021, vol. 23, # 15, p. 5494 - 5502]
[3]Rajamannar, T.; Balasubramanian, K. K. [Tetrahedron Letters, 1986, vol. 27, # 32, p. 3777 - 3780]
[4]Liguori, Francesca; Barbaro, Pierluigi [Journal of Catalysis, 2014, vol. 311, p. 212 - 220]
[5]Vile, Gianvito; Wrabetz, Sabine; Floryan, Leonard; Schuster, Manfred Erwin; Girgsdies, Frank; Teschner, Detre; Perez-Ramirez, Javier [ChemCatChem, 2014, vol. 6, # 7, p. 1928 - 1934]
[6]Suzuki, Hideyuki; Satoh, Ikkyu; Nishioka, Hiromi; Takeuchi, Yasuo [Tetrahedron Letters, 2017, vol. 58, # 40, p. 3834 - 3837]
[7]Fiorio, Jhonatan L.; López, Núria; Rossi, Liane M. [ACS Catalysis, 2017, vol. 7, # 4, p. 2973 - 2980]
[8]Fiorio, Jhonatan Luiz; Gonçalves, Renato Vitalino; Teixeira-Neto, Erico; Ortuño, Manuel A.; López, Núria; Rossi, Liane Marcia [ACS Catalysis, 2018, vol. 8, # 4, p. 3516 - 3524]
[9]Faust Akl, Dario; Ruiz-Ferrando, Andrea; Fako, Edvin; Hauert, Roland; Safonova, Olga; Mitchell, Sharon; López, Núria; Pérez-Ramírez, Javier [ChemCatChem, 2021, vol. 13, # 14, p. 3247 - 3256]

15
[ 23488-38-2 ]
[ 3923-52-2 ]
[ 168787-60-8 ]

Reference： [1]Angewandte Chemie,1994,vol. 106,p. 1856 - 1858

16
[ 5498-31-7 ]
[ 3923-52-2 ]
[ 227471-77-4 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830
[2]European Journal of Organic Chemistry,2003,p. 2799 - 2812

17
[ 7385-87-7 ]
[ 3923-52-2 ]
10-bromo-3,3-diphenyl-<3H>-naphtho<2,1-b>pyran [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830
[2]Journal of the American Chemical Society,2017,vol. 139,p. 13429 - 13441
[3]Chemical Communications,2015,vol. 51,p. 3057 - 3060

18
[ 30159-70-7 ]
[ 3923-52-2 ]
[ 227471-72-9 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830
[2]Magnetic Resonance in Chemistry,2000,vol. 38,p. 775 - 781
[3]Russian Chemical Bulletin,2006,vol. 55,p. 287 - 294
[4]Journal of Physical Organic Chemistry,2007,vol. 20,p. 469 - 483

19
[ 78119-82-1 ]
[ 3923-52-2 ]
[ 227471-74-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With toluene-4-sulfonic acid In dichloromethane Ambient temperature;
71%	With toluene-4-sulfonic acid In dichloromethane at 20℃; for 12h;
56.3%	With toluene-4-sulfonic acid In dichloromethane at 20℃; for 40h; Inert atmosphere;	2.2.1. Synthesis of 3,3-diphenyl-[3H]naphtho[2,1-b]pyran-8-aldehyde(compound a) 1,1-Diphenyl-2-propyn-1-ol (1.668 g, 8 mmol), 6-Hydroxy-2-naphthaldehyde (2.096 g, 12 mmol) and p-toluenesulfonic acid(PTSA) (0.1 equiv.) were added into 60 mL dry CH2Cl2 and stirredunder nitrogen atmosphere at room temperature for 40 h. The reactionmixturewaswashed withwater and dried with anhydrous sodium sulfate.The crude product was purified by column chromatography on silicagel (eluent: CH2Cl2:petroleum ether = 1:2) to give white powder,1.64 g, yield 56.3%. 1H NMR (500 MHz, CDCl3), δ: 10.05 (s, 1H), 8.16(s, 1H), 8.01 (d, 1H, J = 9.0 Hz), 7.92-7.90 (m, 1H), 7.78 (d, 1H, J =8.5 Hz), 7.47 (d, 4H, J = 7.5 Hz), 7.34-7.30 (m, 4H), 7.28-7.24 (m,4H), 6.30 (d, 1H, J = 10 Hz).

Reference： [1]Chamontin, Karine; Lokshin, Vladimir; Rossollin, Valerie; Samat, Andre; Guglielmetti, Robert [Tetrahedron, 1999, vol. 55, # 18, p. 5821 - 5830]
[2]Kahle, Ingolf; Troeber, Oliver; Richter, Hannes; Spange, Stefan [New Journal of Chemistry, 2013, vol. 37, # 5, p. 1479 - 1485]
[3]Gong, Xue; Jiang, Nan; Wang, Guang; Zhang, Heyang; Zhang, Zhuo; Zhong, Tianyuan [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 233]

20
[ 3923-52-2 ]
[ 91136-43-5 ]
[ 227471-73-0 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 5821 - 5830

21
[ 3923-52-2 ]
[ 106-95-6 ]
[ 57900-00-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;
84%	With sodium hydride In N,N-dimethyl-formamide at 20℃;
	Stage #1: 1,1-diphenyl-2-propyn-1-ol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃;

	With sodium hydride In N,N-dimethyl-formamide Ambient temperature; Yield given;
	Stage #1: 1,1-diphenyl-2-propyn-1-ol With sodium hydride In N,N-dimethyl-formamide at -78℃; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at -78 - 60℃; Inert atmosphere;

Reference： [1]Clavier, Herve; Nolan, Steven P. [Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8029 - 8036]
[2]Elias, Xavier; Pleixats, Roser; Man, Michel Wong Chi; Moreau, Joel J. E. [Advanced Synthesis and Catalysis, 2006, vol. 348, # 6, p. 751 - 762]
[3]le Paih, Jacques; Rodríguez, Darío Cuervo; Dérien, Sylvie; Dixneuf, Pierre H. [Synlett, 2000, # 1, p. 95 - 97]
[4]Picquet, Michel; Bruneau, Christian; Dixneuf, Pierre H. [Chemical Communications, 1998, # 20, p. 2249 - 2250]
[5]Grotevendt, Anne G. D.; Lummiss, Justin A. M.; Mastronardi, Melanie L.; Fogg, Deryn E. [Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15918 - 15921]

22
[ 32865-61-5 ]
[ 3923-52-2 ]
acetic acid 2-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃;

Reference： [1]Hu; Yang [Organic letters, 2001, vol. 3, # 9, p. 1387 - 1390]

23
[ 581-43-1 ]
[ 3923-52-2 ]
[ 623580-53-0 ]

Yield	Reaction Conditions	Operation in experiment
19%	With toluene-4-sulfonic acid; In toluene; for 48h;Heating / reflux;	Step 1 3, 3-Diphenyl-3H-benzo[f]chromen-8-ol A stirred suspension of 2, 6-dihydroxy naphthalene (502 mgf, 3. 13 mmol) in toluene (200 mL) was heated to reflux (oil bath temperature 130"C). After .. h, the mixture was homogeneous and p-toluene sulphonic acid hydrate (54 nig, 0. 28 nunol) was added followed by a solution of 1, 1-diphenyl-prop-2-yn-1-ol (588 mg, 2.82 mmol) in toluene (40 mL over 30 min while maintaining reflux. After 2 d, the mixture was cooled to room temperature and washed with aqucous sodium hydroxide solution (10%, 400 mL). The organic phase was diluted with ethyl acctate (200 mL), dried (Na2SO4). filtered and concontrated in vacuo to afford a black solid. This was dissolved in chloroform/hexane (5 nl : 5 t) and subjected to flash chromatography, eluting with chloroform/hexane 1:1 then neat cliloroform. 3, 3-Diphenyl-3H-benzo[f]chromen-8-ol was obtained as a brown solid (213 mg, 19%): MS (ESI-) m/z 287 (M-1). HPLC 80.3% 8.89 min
19%	toluene-4-sulfonic acid; In toluene; at 130℃; for 48h;Heating / reflux;	A stirred suspension of 2,6-dihydroxy naphthalene (502 mg, 3.13 mmol) in toluene (200 mL) was heated to reflux (oil bath temperature 130 C.). After 1 h, the mixture was homogeneous end p-toluene sulphonic acid hydrate (54 mg, 0.28 mmol) was added followed by a solution of 1,1-diphenyl-prop-2-yn-1-ol (588 mg, 2.82 mmol) in toluene (40 mL) over 30 min while maintaining reflux. After 2 d, the mixture was cooled to room temperature and washed with aqueous sodium hydroxide solution (10%, 400 mL). The organic phase was diluted with ethyl acetate (200 mL), dried (Na2SO4, filtered and concentrated in vacuo to afford a black solid. This was dissolved in chloroform/hexane (5 mL:5 ml) and subjected to flash chromatography, eluding with chloroform/hexane 1:1 then neat chloroform. 3,3-Diphenyl-3H-benzo[f]chromen-8-ol was obtained as a brown solid (213 mg, 19%): MS (ESI-) m/z 287 (M-1). HPLC 80.3%/8.89 min

Reference： [1]Organic Letters,2003,vol. 5,p. 4153 - 4154
[2]Patent: WO2005/95376,2005,A1 .Location in patent: Page/Page column 45-46
[3]Patent: US2009/170926,2009,A1 .Location in patent: Page/Page column 17

24
[ 78250-21-2 ]
[ 3923-52-2 ]
[ 200884-10-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Heating;
56%	In toluene at 40 - 90℃; for 6h;	3 The synthesis of M7a has the following reaction formula: The 10.0g M6a,12.66g 1,1- diphenyl-2-propyn -1-ol with 200ml of toluene was added toIn a 500 ml round bottom flask, heat to 40 ° C, stir well,The temperature was raised to 90 ° C for 6 h, the temperature was lowered to room temperature, and the solvent was evaporated under reduced pressure.Add 100 ml of methyl tert-butyl ether and warm to 50 ° C.150 ml of petroleum ether was added dropwise to the round bottom flask, and after the addition,Stir at 50 ° C for 1.5 h, cool to room temperature, suction filtration,The filter cake was rinsed with cold methyl tert-butyl ether and dried in vacuo. The yield was 56%.
50%	With toluene-4-sulfonic acid In toluene; butanone at 20℃; for 2h; Reflux; Inert atmosphere;	4.3.1. Synthesis of 3,3-diphenylbenzo [3,4] fluoreno[2,1-b]pyran-13(3H)-one 13-3 To a refluxing solution of 5-hydroxy-7H-benzo[c]fluoren-7-one 12-3 (4.43 g, 17.99 mmol) in a mixture of toluene (180 mL) and 2-butanone (50 mL) were added 1,1-diphenylpropyn-1-ol (5.67 g,27.2 mmol) and catalytic amount of p-TsOH, and the resulting mixture was refluxed for 2 h. The solution was cooled down toroom temperature, then 10% aq. sodium hydroxide (21 mL), tetrahydrofuran(230 mL) and 10% aq. sodium chloride were added and the mixture was stirred well. The organic layer was separated, washed with water four times, and the solvent removed in vacuo. To the resulting residue was added acetone (90 mL) and the mixture was refluxed for 1.5 h. After the mixture was cooled down, the solid material precipitated was collected by filtration. After drying in vacuo, 3,3-diphenylbenzo[3,4]fluoreno[2,1-b]pyran-13(3H)-one 13-3 was obtained as a dark purple solid (3.91 g, 8.96 mmol) in 50% yield. 13-3: Mp 253-255 °C. 1H NMR (CDCl3) δ/ppm 6.36 (1H, d, J = 10.4 Hz), 7.19 (1H, t, J = 8.0 Hz), 7.26 (4H, t, J = 6.8 Hz), 7.32 (4H, t, J = 7.2 Hz), 7.43 (1H, t, J = 8.0 Hz), 7.51 (4H, d, J = 8.8 Hz), 7.56 (3H, m), 7.86 (1H, d, J = 7.2 Hz), 7.91 (1H, d, J = 9.6 Hz), 8.38 (2H, m). LC-MS Observed 437.1649 (M+1) (Calculated exact mass for C32H21O2 (M+1) 437.1536). FT-IR (KBr) ν/cm-1 3054, 3026, 1700, 1601, 1490, 1463, 1398, 1369, 1338, 1274.

With DBSA In toluene at 50℃; for 144h;

1.5 Example 1; step 5 5-Hydroxy-7H-benzo[c]fluoren-7-one (8 grams), from Step 4, was added to a reaction flask containing 1,1-diphenyl-2-propyn-1-ol (7.3 grams) and 75 mL of toluene. The resulting mixture was stirred and heated to 50C., three drops of dodecybenzene sulfonic acid were added, and the reaction mixture was kept at 50C. for 6 days. After the reaction mixture cooled to room temperature, it was filtered and the collected filtrate was washed with 5 weight percent aqueous sodium hydroxide until the washings were colorless. The residual solid was washed with a 10:1 solvent mixture of ether:acetone, dissolved in chloroform and recrystallized from chloroform /hexane. The recovered product, 7.18 grams, had a melting point of 254C and a nuclear magnetic resonance spectrum (NMR) showing the product to have a structure consistent with 3,3-diphenyl-13-oxo-1H-indeno[2,1-f]naphtho[1,2-b]pyran.

Reference： [1]Zhao, Weili; Carreira, Erick M. [Organic Letters, 2003, vol. 5, # 22, p. 4153 - 4154]
[2]Current Patent Assignee: TIANJIN UVOS TECH - CN108623554, 2018, A Location in patent: Paragraph 0082; 0086-0088
[3]Momoda, Junji; Izumi, Shinobu; Yokoyama, Yasushi [Dyes and Pigments, 2015, vol. 119, p. 95 - 107]
[4]Current Patent Assignee: PPG INDUSTRIES INC; THOMAS JEFFERSON UNIVERSITY - EP906366, 2003, B1 Location in patent: Page 11

25
[ 3923-52-2 ]
[ 622-79-7 ]
(1-benzyl-1H-[1,2,3]triazol-4-yl)-diphenyl-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(II) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 5h;
94%	With 2,6-dimethylpyridine In water at 20℃; for 3h; regioselective reaction;
93%	With SiO₂/γ-Fe₂O₃ nanoparticle-supported tris(triazolyl)-CuBr In water at 23 - 25℃; for 20h; Inert atmosphere; Schlenk technique; Green chemistry;

90%	With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90℃; for 0.0833333h; Inert atmosphere; regioselective reaction;
90%	With Cu(I)complex of dendrimer of triazole rings with triethylene glycol termini In water at 30℃; for 24h; Inert atmosphere;
63%	With copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 24h; Darkness; Inert atmosphere;
	With Ru(κ²-OAc)₂(PPh₃)₂ In benzene for 4h; Heating;
	With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90℃; for 0.0833333h;

Reference： [1]Hosseinzadeh, Rahman; Abolfazli, Mohammadreza Khadem; Mohseni, Mojtaba; Mohadjerani, Maryam; Lasemi, Zahra [Journal of Heterocyclic Chemistry, 2015, vol. 51, # 5, p. 1298 - 1305]
[2]Garcia-Alvarez, Joaquin; Diez, Josefina; Gimeno, Jose [Green Chemistry, 2010, vol. 12, # 12, p. 2127 - 2130]
[3]Wang, Dong; Etienne, Laetitia; Echeverria, Maria; Moya, Sergio; Astruc, Didier [Chemistry - A European Journal, 2014, vol. 20, # 14, p. 4047 - 4054]
[4]Zhang, Huan; Tanimoto, Hiroki; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi [Organic Letters, 2013, vol. 15, # 20, p. 5222 - 5225]
[5]Deraedt, Christophe; Pinaud, Noël; Astruc, Didier [Journal of the American Chemical Society, 2014, vol. 136, # 34, p. 12092 - 12098]
[6]Krittametaporn, Nuttaporn; Chantarojsiri, Teera; Virachotikul, Arnut; Phomphrai, Khamphee; Kuwamura, Naoto; Kojima, Tatsuhiro; Konno, Takumi; Sangtrirutnugul, Preeyanuch [Dalton Transactions, 2020, vol. 49, # 3, p. 682 - 689]
[7]Zhang, Li; Chen, Xinguo; Xue, Peng; Sun, Herman H. Y.; Williams, Ian D.; Sharpless, K. Barry; Fokin, Valery V.; Jia, Guochen [Journal of the American Chemical Society, 2005, vol. 127, # 46, p. 15998 - 15999]
[8]Zhang, Huan; Tanimoto, Hiroki; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi [Tetrahedron, 2014, vol. 70, # 52, p. 9828 - 9835]

26
[ 612-76-0 ]
[ 3923-52-2 ]
C₄₂H₃₀O₂ [ No CAS ]
C₄₂H₃₀O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1354 - 1357

27
[ 698-70-4 ]
[ 3923-52-2 ]
[ 77251-02-6 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 2231 - 2233

28
[ 696-62-8 ]
[ 3923-52-2 ]
[ 35476-69-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 20h; Reflux; Inert atmosphere;	7 Example 7 In a 100 mL three-necked flask purged with nitrogen, 2.09 g of 4-iodoanisole,1.86 g of 1-diphenyl-2-propyn-1-ol, 0.025 g of triphenylphosphine, 0.0125 g of bis (triphenylphosphine) palladium (II) dichloride,0.0125 g of CuI (I), and 40 mL of triethylamine,The mixture was heated to reflux for 4 hours,Further stirring was continued at room temperature for 16 hours for reaction.After completion of the reaction,After neutralizing the reaction solution with a 5% hydrochloric acid aqueous solution,The organic phase was extracted with ethyl acetate,The obtained extract was dried using anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was recrystallized from ethanol to obtain 1.91 g (yield: 68%) of white crystals.Identification of the obtained white crystals was carried out by 1 H-NMR (see FIG. 8) and MS,The purity was 99% or more (LC,Area%). Based on the above analysis results,The white crystal could be identified as a compound of formula (1 g
	With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: DEXERIALS CORPORATION - JP5821662, 2015, B2 Location in patent: Paragraph 0017; 0088; 0091
[2]Horita, Akinobu; Tsurugi, Hayato; Funayama, Atsushi; Satoh, Tetsuya; Miura, Masahiro [Organic Letters, 2007, vol. 9, # 11, p. 2231 - 2233]
[3]Okamoto, Noriko; Sueda, Takuya; Yanada, Reiko [Journal of Organic Chemistry, 2014, vol. 79, # 20, p. 9854 - 9859]

29
[ 22802-37-5 ]
[ 3923-52-2 ]
[ 949111-78-8 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8242 - 8249

30
[ 50-00-0 ]
[ 3923-52-2 ]
[ 494-52-0 ]
[ 1072878-51-3 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 1637 - 1647

31
[ 15555-77-8 ]
[ 3923-52-2 ]
[ 2622-14-2 ]
RuCl₂(=C=C=CPh₂)(PCy₃)2 [ No CAS ]

Reference： [1]Organometallics,1999,vol. 18,p. 5187 - 5190

32
sodium hexaflorophosphate [ No CAS ]
[ 52490-94-5 ]
[ 3923-52-2 ]
[ 210570-09-5 ]

Reference： [1]Chemical Communications,1998,p. 1315 - 1316

33
[Ru(hydrido trispyrazolylborate)(η4-cycloocta-1,5-diene)Cl] [ No CAS ]
[ 3923-52-2 ]
[ 6372-40-3 ]
[Ru(HB(C₃H₃N₂)3)(P(C₆H₅)2CH(CH₃)2)(CCHC(C₆H₅)2OH)Cl] [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2005,vol. 690,p. 5497 - 5507

34
[ 2437-17-4 ]
[ 3923-52-2 ]
[ 1131147-87-9 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3062 - 3065

35
[ 937021-07-3 ]
[ 3923-52-2 ]
[ 1263214-78-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃;	4.1.2. 2-{4-[4-(Hydroxy-diphenyl-methyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxy-ethyl ester (3c) To a solution of alkynol 1c (2.41 g, 2.83 mmol) and azide 2 (1 equiv) in THF/H2O (1/1, 80 mL) were added sodium ascorbate (95.5 mg, 0.48 mmol) and CuSO4·5H2O (60.5 mg, 0.24 mmol). After being stirring overnight at ambient temperature, the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried with MgSO4 and concentrated in vacuo. The residue was purified (flash chromatography, silica gel, 20-50% gradient EA/PE) to provide 1.11 g (92%) of alcohol 3c as solid (mp 104-105 °C). CCM: PE/EA: 50/50 Rf=0.26; CH2Cl2/MeOH: 95/5 Rf=0.54; HPLC: MeOH/H2O 70/30% (0.1% TFA), rt=4.54 min. 1H NMR (400 MHz, DMSO): δ ppm: 7.85 (s, 1H), 7.64 (dd, 1H, J=7.5, 1.7 Hz), 7.51 (ddd, 1H, J=8.3, 7.5, 1.7 Hz), 7.21-7.38 (m, 10H), 7.11 (d, 1H, J=8.3 Hz), 7.01 (t, 1H, J=7.5 Hz), 6.54 (s, 1H), 4.44 (t, 2H, J=7.0 Hz), 4.30 (t, 2H, J=4.6 Hz), 4.05 (t, 2H, J=6.0 Hz), 3.57 (t, 2H, J=4.6 Hz), 3.24 (s, 3H), 2.03 (m, 2H), 1.70 (m, 2H); 13C NMR (100 MHz, DMSO): δ ppm: 165.7, 157.4, 153.7, 147.0, 133.5, 130.7, 127.4, 126.9, 126.5, 123.1, 120.1, 120.0, 113.4, 75.6, 69.7, 68.5, 63.4, 57.9, 48.9, 26.5, 25.5; HRMS (TOF MS ES+) calcd for [M+H]+ C29H32N3O5: 502.2342, found 502.2335; IR: ν cm-1: 3209, 1719, 1448, 1649, 1091, 1020, 755, 702.
92%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 25℃; Inert atmosphere;
	With copper(l) iodide In tetrahydrofuran; water at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Delatouche, Regis; Mondon, Martine; Gil, Adri; Frapper, Gilles; Bachmann, Christian; Bertrand, Philippe [Tetrahedron, 2011, vol. 67, # 2, p. 401 - 407]
[2]Mondon, Martine; Delatouche, Regis; Bachmann, Christian; Frapper, Gilles; Len, Christophe; Bertrand, Philippe [European Journal of Organic Chemistry, 2011, # 11, p. 2111 - 2119]
[3]Location in patent: scheme or table Delatouche, Regis; Bachmann, Christian; Frapper, Gilles; Bertrand, Philippe [Synthesis, 2012, vol. 44, # 7, p. 1090 - 1094]

36
[ 119-61-9 ]
[ 1066-54-2 ]
[ 3923-52-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone at -10 - 20℃; for 4h; Stage #3: With potassium hydroxide In methanol for 0.5h;
96%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -10 - 0℃; for 3h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; hexane at 0 - 20℃; Inert atmosphere;
92%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane for 4h; Inert atmosphere; Stage #3: With potassium hydroxide In tetrahydrofuran; methanol; hexane at 20℃; for 0.5h;	2.3.2. Synthesis of 1,1-diphenyl-2-yn-1-ol (M1) Trimethylsiylacetylene (1.2 mL, 8.0 mmol) and n-butyllithium inhexanes (3.7 mL, 8.0 mmol) were added into anhydrous THF (15 mL) at 10 C via syringe nitrogen atmosphere. After stirring for 1 h, diphenylketone (1385 mg, 7.6 mmol) was added and the reaction mixture wasstirred for another 4 h. A methanol solution (10 mL) of KOH (898 mg, 16mmol) was added into the above solution, and the solution was warmedto room temperature for 0.5 h and the mixture was neutralized withacetic acid and extracted with DCM. The organic solution was washedwith brine and dried with anhydrous sodium sulfate. The pure M1 wasobtained by column chromatography on silica gel (ethyl acetate: petroleumether 1: 20) as 1459 mg slight yellow solid with a yield of92%. 1H NMR (500 MHz, DMSO-d6, 25 C) (, ppm): 7.53 (m, 4H, Ar-H),7.33 (m, 4H, Ar-H), 7.24 (m, 2H, Ar-H), 6.80 (s, 1H, OH), 3.80 (s, 1H,C- - -CH). 13C NMR (125 MHz, CDCl3, 25 C) (, ppm): 144.3, 128.3,127.9, 125.9, 86.3, 75.6, 74.3. FT-IR (KBr, cm 1) max: 3554 (O-H),3275 (C-H), 3083, 3060, 3026 (Ar, C-H), 2116 (C- - -C), 1597, 1489,1449 (Ar, C-C), 1097 (C-C), 1052 (C-O). MALDI-TOF-MS m/z: calc. forC15H12O [M H] : 209.1; found 209.1.

88.4%	Stage #1: benzophenone; trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 4h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol at 0℃;	1,1-Diphenyl-prop-2-yn-1-ol 1c.[1] General procedure: To a solution of (trimethylsilyl)acetylene (4.5 g, 45 mmol) in anhydrous THF (150 mL) under nitrogen atmosphere was added slowly n-BuLi (1.6 M in hexane, 28.5 mL, 45 mmol) at -10°C and the solution stirred 1h at - 10°C. A solution of benzophenone (7.44 g, 40.8 mmol) in dry THF (75 mL) was then added at -10°C. After 3h stirring at -10°C, the temperature was raised to 0°C and a solution of NaOH (2.16 g, 54 mmol) in MeOH (40,8 mL) was added. After the solution was warmed to room temperature, the solution was neutralized to pH 7 with acetic acid and the resulting solution poured into water (546 mL). The organic layer was extracted with EA (3x105 mL). The combined organic layers were dried over MgSO4. The crude product was recristallized from EA/PE to give 7,5 g of 1c as a light yellow solid (88,4%). 1H NMR (300 MHz, DMSO): δ ppm: 3.96 (s, 1H), 6.89 (s, 1H ), 7.21 (m, 2H), 7.38 (t, 4H, J = 7.2 Hz), 7.59 (d, 4H, J = 7.3 Hz); 13C NMR (75 MHz, CDCl3): δ ppm: 74.3, 75.6, 86.4, 126.0, 127.8, 128.3, 144.4. Mp: 45,1°C-47,7°C ; CCM: PE/EA: 90/10, Rf=0.46; IR ν cm-1: 3550, 3275, 2117, 1597, 1489, 1448, 1155, 991, 752, 686, 641.
88.4%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -10℃; for 3h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; hexane at 0 - 20℃; Inert atmosphere;
87%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at 20℃; for 4h; Inert atmosphere; Stage #3: With potassium hydroxide In methanol at 0℃; for 0.333333h; Inert atmosphere;

Reference： [1]Olaizola, Iurre; Campano, Teresa E.; Iriarte, Igor; Vera, Silvia; Mielgo, Antonia; García, Jesús M.; Odriozola, José M.; Oiarbide, Mikel; Palomo, Claudio [Chemistry - A European Journal, 2018, vol. 24, # 15, p. 3893 - 3901]
[2]Deng, Hui; Kooijman, Sander; Van Den Nieuwendijk, Adrianus M. C. H.; Ogasawara, Daisuke; Van der Wel, Tom; Van Dalen, Floris; Baggelaar, Marc P.; Janssen, Freek J.; Van Den Berg, Richard J. B. H. N.; Den Dulk, Hans; Cravatt, Benjamin F.; Overkleeft, Herman S.; Rensen, Patrick C. N.; Van der Stelt, Mario [Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 428 - 440]
[3]Dong, Wenyue; Duan, Qian; Gao, Bo; Liu, Dajun; Wang, Jihua [Dyes and Pigments, 2020, vol. 182]
[4]Delatouche, Regis; Mondon, Martine; Gil, Adri; Frapper, Gilles; Bachmann, Christian; Bertrand, Philippe [Tetrahedron, 2011, vol. 67, # 2, p. 401 - 407]
[5]Mondon, Martine; Delatouche, Regis; Bachmann, Christian; Frapper, Gilles; Len, Christophe; Bertrand, Philippe [European Journal of Organic Chemistry, 2011, # 11, p. 2111 - 2119]
[6]Dimakos, Victoria; Singh, Tishaan; Taylor, Mark S. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 28, p. 6703 - 6711]

37
[ 3923-52-2 ]
[ 119-61-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With ozone In chloroform at 25℃; Stage #2: With dihydrogen peroxide In chloroform at 25℃;
83%	With Tp(PPh<SUB>3</SUB>)(HN=CPh<SUB>2</SUB>)Ru-Cl; oxygen In methanol at 20℃; for 4h; Inert atmosphere; Schlenk technique;	3.2. Procedure for catalytic reactions General procedure: In a 25 mL Schlenk tube equipped with a Teflon stopcock, theruthenium catalyst Tp(PPh3)(NHCPh2)Ru-Cl (1, 5 mol %) in 1 mLof methanol. Excess 1,1-diphenylpropargyl alcohol (0.80 mmol)was added to the solution, and the reaction mixture was stirred atroom temperature for 4 h. Then the solution was evaporated underhigh vacuum. The residue was extracted with Et2O, and the Et2Osolution was chromatographed on silica gel (n-hexane/Et2O) in air.The rotary evaporation led to the ketone products.
	With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride

Reference： [1]Irfan, Muhammad; Glasnov, Toma N.; Kappe, C. Oliver [Organic Letters, 2011, vol. 13, # 5, p. 984 - 987]
[2]Lo, Yih-Hsing; Li, Ming-Che; Huang, Li-Yu; Hung, Guan-Jie [Journal of Organometallic Chemistry, 2017, vol. 830, p. 109 - 112]
[3]Location in patent: body text Shirinian, Valerii Z.; Shimkin, Aleksei A.; Mailyan, Artur K.; Leonova, Evgeniya S.; Krayushkin, Mikhail M. [Mendeleev Communications, 2011, vol. 21, # 6, p. 339 - 340]

38
[ 3923-52-2 ]
[ 517-51-1 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 4160 - 4169

39
[ 1374327-16-8 ]
[ 3923-52-2 ]
[ 1374326-87-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With CuI; triethylamine; triphenylphosphine In N,N-dimethyl-formamide	4 Synthesis of E4 Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate (6). A solution of 5 (0.47 g, 1.3 mmol), 1,1-diphenylprop-2-yn-1-ol (0.66 g, 3.2 mmol), CuI (0.05 g, 0.3 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.3 mmol), PPh3 (0.07 g, 0.3 mmol), and Et3N (4 mL) in anhydrous DMF (4 mL) was stirred for 16 hours at 70° C. under N2 atmosphere. The reaction mixture was partitioned between water and EtOAc. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 6 as a pale yellow solid (0.49 g, 87%). 1H NMR (400 MHz, CDCl3) δ 9.88 (s, 1H), 7.50-7.52 (m, 4H), 7.36 (s, 1H), 7.24-7.30 (m, 8H), 7.04 (m, 2H), 5.69 (s, 2H), 3.80 (s, 3H), and 3.65 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 185.16, 160.72, 144.07, 136.84, 128.91, 128.72, 128.33, 127.91, 127.79, 127.05, 126.23, 124.96, 116.97, 103.35, 75.37, 75.27, 52.15, and 50.38.
87%	With CuI; triethylamine; triphenylphosphine In N,N-dimethyl-formamide	6 Synthesis of E6 Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate (6). A solution of 5 (0.47 g, 1.3 mmol), 1,1-diphenylprop-2-yn-1-ol (0.66 g, 3.2 mmol), CuI (0.05 g, 0.3 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.3 mmol), PPh3 (0.07 g, 0.3 mmol), and Et3N (4 mL) in anhydrous DMF (4 mL) was stirred for 16 hours at 70° C. under N2 atmosphere. The reaction mixture was partitioned between water and EtOAc. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 6 as a pale yellow solid (0.49 g, 87%). 1H NMR (400 MHz, CDCl3) δ 9.88 (s, 1H), 7.50-7.52 (m, 4H), 7.36 (s, 1H), 7.24-7.30 (m, 8H), 7.04 (m, 2H), 5.69 (s, 2H), 3.80 (s, 3H), and 3.65 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 185.16, 160.72, 144.07, 136.84, 128.91, 128.72, 128.33, 127.91, 127.79, 127.05, 126.23, 124.96, 116.97, 103.35, 75.37, 75.27, 52.15, and 50.38.
87%	With CuI; triethylamine; triphenylphosphine In N,N-dimethyl-formamide	8 Synthesis of E6b Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate (6). A solution of 5 (0.47 g, 1.3 mmol), 1,1-diphenylprop-2-yn-1-ol (0.66 g, 3.2 mmol), CuI (0.05 g, 0.3 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.3 mmol), PPh3 (0.07 g, 0.3 mmol), and Et3N (4 mL) in anhydrous DMF (4 mL) was stirred for 16 hours at 70° C. under N2 atmosphere. The reaction mixture was then partitioned between water and EtOAc. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 6 as a pale yellow solid (0.49 g, 87%). 1H NMR (CDCl3) δ 9.88 (s, 1H), 7.50-7.52 (m, 4H), 7.36 (s, 1H), 7.24-7.30 (m, 8H), 7.04 (m, 2H), 5.69 (s, 2H), 3.80 (s, 3H), and 3.65 (s, 1H); 13C NMR (CDCl3) δ 185.16, 160.72, 144.07, 136.84, 128.91, 128.72, 128.33, 127.91, 127.79, 127.05, 126.23, 124.96, 116.97, 103.35, 75.37, 75.27, 52.15, and 50.38.

Reference： [1]Current Patent Assignee: MAYO FOUNDATION - US2012/114696, 2012, A1
[2]Current Patent Assignee: MAYO FOUNDATION - US2012/114696, 2012, A1
[3]Current Patent Assignee: MAYO FOUNDATION - US2012/114696, 2012, A1

40
[ 35578-47-3 ]
[ 3923-52-2 ]
[ 1383486-16-5 ]

Reference： [1]New Journal of Chemistry,2012,vol. 36,p. 1469 - 1478

41
[ 106-44-5 ]
[ 3923-52-2 ]
[ 1397746-29-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With β‐cyclodextrin In water at 60℃; for 5h; Green chemistry; regioselective reaction;
82%	With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 6.5h;	Typical experimental procedure for preparation of 2,2,6-trimethyl-2H-chromene (3b): General procedure: p-Cresol 1b (1.0 g, 9.21 mmol), 2-methyl-3-butyn-2-ol 2 (0.77 g, 9.21 mmol, 0.8 mL) and dichloromethane (10 mL) were taken into a 50 mL round-bottomed flask fitted with a condenser and calcium chloride guard tube. To this, BF3·Et2O (0.26 g, 1.8 mmol, 0.2 mL) was added and the mixture was stirred at room temperature for 6 h. After completion of the reaction (TLC), solvent was removed from the mixture under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, n-hexane) to obtain 6-methyl-2,2-dimethyl-2H-chromene 3b (1.34 g, 84%) as a colorless oil,

Reference： [1]Ghatak, Avishek; Khan, Sagar; Bhar, Sanjay [Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 435 - 443]
[2]Madabhushi, Sridhar; Jillella, Raveendra; Godala, Kondal Reddy; Mallu, Kishore Kumar Reddy; Beeram, China Ramanaiah; Chinthala, Narsaiah [Tetrahedron Letters, 2012, vol. 53, # 39, p. 5275 - 5279]

42
[ 1430325-25-9 ]
[ 3923-52-2 ]
C₁₈₀H₁₅₆O₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	4.2.15 General procedure for the Sonogashira cross coupling reaction. Dendrimer 16b General procedure: An oven-dried vessel was charged with the aryl iodide (80 mg, 0.036 mmol), the terminal alkyne (157 mg, 0.25 mmol), Pd(PPh3)2Cl2 (9 mg, 0.0125, 5 mol%), and CuI (5 mg, 0.025 mmol, 10 mol%). The vessel was evacuated and backfilled with argon three times. To the vessel, degassed DMF (5 mL) and degassed triethylamine (1 mL) were added. (0039) The mixture was stirred at 80°C overnight. After filtration through Celite, the solvent was evaporated and the resulting residue was taken into CH2Cl2 (30 mL) and washed with brine (15 mL). The organic layer was separated, dried and evaporated and the crude purified by size exclusion column chromatography (100% CH2Cl2)

Reference： [1]Villalonga-Barber, Carolina; Vallianatou, Kalliopi; Georgakopoulos, Spyros; Steele, Barry R.; Micha-Screttas, Maria; Levin, Efrat; Gabriel Lemcoff [Tetrahedron, 2013, vol. 69, # 19, p. 3885 - 3895]

43
[ 5580-79-0 ]
[ 3923-52-2 ]
[ 1417372-64-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tetrakis(triphenylphosphine) palladium(0); In dimethyl sulfoxide; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	General procedure: Pd(PPh3)4 (0.05equiv) was charged to a 0.5-2.0 ml microwave vial, which was sealed and purged with argon to create an inert atmosphere. Dry, degassed DMSO (1.9ml), phenyl acetylene (1.1equiv) and pentafluoronitrobenzene (1.0equiv) were added in sequence to the vial, which was then heated to 120C for 20 min under microwave irradiation. The reaction mixture was cooled and filtered through an alumina plug with DCM as the eluent to remove inorganic and particulate material. The organic washings were concentrated in vacuo, poured onto water (100ml) and extracted with DCM (3×100ml). The organic fractions were combined, washed with water (100ml) and dried (MgSO4). Volatiles were removed in vacuo and the desired product was purified by either column chromatography using silica gel using a mixture of hexane and DCM (1:9) as the eluent or by Kugelrohr distillation.

Reference： [1]Tetrahedron,2013,vol. 69,p. 512 - 516

44
[ 7755-70-6 ]
[ 3923-52-2 ]
4-hydroxy-1-(2-(methylamino)phenyl)-4,4-diphenylbut-2-yn-1-one [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4110 - 4113

45
[ 7755-70-6 ]
[ 3923-52-2 ]
C₂₃H₂₁NO₂ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4110 - 4113

46
6,7-bis(2-hydroxyethoxy)naphthalen-2-ol [ No CAS ]
[ 3923-52-2 ]
8,9-bis(2-hydroxyethoxy)-3,3-diphenyl-3H-benzo[f]chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With toluene-4-sulfonic acid In toluene at 50 - 80℃; for 4h;	Method 1 (with the use of diphenylpropargyl alcohol) The procedure was adopted from lit.S2 Substituted phenol or naphthol (0.6 mmol) and 1,1-diphenylprop-2-in-1-ol (0.6 mmol) were dissolved in 10 ml of toluene and PTSA (0.06 mmol) was added. The mixture was stirred at 50-60°C for 1 h and then at 70-80°C for additional 3 h. Afterwards the solvent was evaporated and the product was isolated by column chromatography.

Reference： [1]Paramonov, Sergey V.; Lokshin, Vladimir; Fedorova, Olga A. [Synthesis, 2014, vol. 46, # 12, p. 1659 - 1666]

47
[ 92748-09-9 ]
[ 3923-52-2 ]
2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 242 - 245

48
[ 3923-52-2 ]
1,3-dihydroxy-1,1-diphenylpropan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With iodobenzene; trifluoroacetic anhydride In water; acetonitrile at 20 - 90℃; for 28h;	Experimental General procedure: A solutionof3.1goxone,2.0mltrifluoroaceticanhydride,and10mlH2O wasstirredfor 4hat40°Candthencooledtoroomtemperature.2-Phenylbut-3-yn-2-ol(292mg,2 mmol)andiodobenzene(41mg,0.2mmol)in30mlCH3CN wereaddedatroomtem-perature. Theresultingsolutionwasstirredfor24hat90°C.(Theprogressofthereactionwas monitoredbythin-layerchromatography,TLC.)Then10mlCH2Cl2 was added.Themixture wasneutralizedwithacooled10% aqueous sodiumcarbonatesolutionandextracted withCH2Cl2 (100 ml3). Thecombinedorganicphasewaswashedwithbrine,dried overanhydrousMgSO4, filtered,andconcentrated.Theresiduewaspurifiedbycol-umn chromatography[silicagel(200-300mesh),petroleumether-EtOAc(8:1)]togive1,3-dihydroxy-3-phenylbutan-2-one (273.7mg,76%).
	Multi-step reaction with 2 steps 1: acetic acid / 100 °C / Sealed tube 2: hydrogenchloride / methanol; water / 20 °C

Reference： [1]Chen, Chengqun; You, Minghua; Chen, Hong [Synthetic Communications, 2016, vol. 46, # 1, p. 73 - 78]
[2]Liu, Qing-Rong; Pan, Cheng-Xue; Ma, Xiao-Pan; Mo, Dong-Liang; Su, Gui-Fa [Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6496 - 6501]

49
[ 3923-52-2 ]
[ 100-51-6 ]
[ 1210-39-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With ferrocenium hexafluorophosphate In dichloromethane at 40℃; for 72h;	Meyer-Schuster rearrangement of 1,1-diphenyl-2-propyn-3-ol(Scheme 2, bottom) 1,1-diphenylprop-2-yn-1-ol (0.145 g, 0.697 mmol), benzyl alcohol (0.073 g, 0.678 mmol), and [Fc]PF6(0.007 g,0.021 mmol) were combined in CH2Cl2(3 mL) and heated at 40Cfor 3 days. The solvent was removed and the residue filteredthrough a short pad of silica gel. From the recovered mass (0.192 g),an NMR yield of 84% for the aldehyde 13 was calculated. The NMRshowed besides the rearranged product only benzyl alcohol. NMR(, CDCl3)1H: 9.43 (d, 0.65H,2JHH= 8.0 Hz, HC = O of 13), 7.35-7.20(m, 18.3H, aromatic), 6.51 (d, 0.65H,2JHH= 8.0 Hz, CHCHO of 13),4.75 (s, 2H, CH2OH of benzyl alcohol), 2.55 (s, 1H, CH2OH of benzylalcohol). IR (ATR, neat): 3054 (w), 2840 (w), 1659 (s), 1589 (m),1488 (m), 1442 (s), 1340 (s), 1263 (s), 1122 (s), 1028 (m), 768 (s),731 (s) cm-1.

Reference： [1]Queensen, Matthew J.; Rabus, Jordan M.; Bauer, Eike B. [Journal of Molecular Catalysis A: Chemical, 2015, vol. 407, p. 221 - 229]

50
[ 60-12-8 ]
[ 3923-52-2 ]
(1-(2-phenethoxy)prop-2-yne-1,1-diyl)dibenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With ferrocenium hexafluorophosphate In dichloromethane at 40℃; for 5h; Sealed tube;	(1-Phenethoxyprop-2-yne-1,1-diyl)dibenzene (Table 2, entry12) General procedure: 1,1-Diphenyl-2-propyn-3-ol (0.099 g, 0.473 mmol), 2-phenylethanol (0.059 g, 0.500 mmol), and [Fc]PF6(0.005 g,0.015 mmol) were combined and worked up as describedabove for 1-(methoxy)prop-2-yne-1,1-diyl)dibenzene to give(1-phenethoxyprop-2-yne-1,1-diyl)dibenzene as a yellow oil(0.055 g, 0.168 mmol, 35%).

Reference： [1]Queensen, Matthew J.; Rabus, Jordan M.; Bauer, Eike B. [Journal of Molecular Catalysis A: Chemical, 2015, vol. 407, p. 221 - 229]

51
[ 3923-52-2 ]
[ 71-36-3 ]
[ 18215-56-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With ferrocenium hexafluorophosphate In dichloromethane at 40℃; for 5h; Sealed tube;	(1-Butoxyprop-2-yne-1,1-diyl)dibenzene (Table 2, entry 11) General procedure: 1,1-Diphenyl-2-propyn-3-ol (0.104 g, 0.501 mmol), n-butanol (0.037 g,0.502 mmol), and [Fc]PF6(0.005 g, 0.014 mmol) were combinedand worked up as described above for (1-methoxy-prop-2-yne-1,1-diyl)dibenzene to give (1-butoxyprop-2-yne-1,1-diyl)dibenzeneas a yellow oil (0.050 g, 0.189 mmol, 40

Reference： [1]Queensen, Matthew J.; Rabus, Jordan M.; Bauer, Eike B. [Journal of Molecular Catalysis A: Chemical, 2015, vol. 407, p. 221 - 229]

52
[ 130-03-0 ]
[ 3923-52-2 ]
2-(3,3-diphenylprop-2-en-1-ylidene)-1-benzothiophen-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With toluene-4-sulfonic acid; In acetonitrile; for 1h;Inert atmosphere; Reflux;	General procedure: To a stirred mixture of ketone 1a or 1b (3 mmol) and diarylpropargylic alcohols 2a-e (3 ml) in acetonitrile (3 ml) the corresponding catalyst (Table 1) was added and the reaction mixture was refluxed under argon for 1 h. After cooling, the solvent was distilled off in vacuo. The residue was purified by recrystallization from the corresponding solvent or by chromatography on silica gel using the light petroleum/ethyl acetate (8:1) system as an eluent.

Reference： [1]Mendeleev Communications,2015,vol. 25,p. 262 - 263

53
[ 1189179-55-2 ]
[ 3923-52-2 ]
N-(benzo[d]thiazol-2-yl)-2-(4-(hydroxydiphenylmethyl)-1H-1,2,3-triazol-1-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate In water; <i>tert</i>-butyl alcohol at 20℃; for 4h; Sonication; Inert atmosphere; regioselective reaction;	Method b: General procedure: A mixture of equimolar amounts of azidobenzothiazole 3a-c and terminal alkyne 4a-f, CuSO4 (0.01 eq) and Na-ascorbate (0.01 eq) in t-BuOH and water (1:1) was sonicated for 3-6 h at room temperature under inert atmosphere in a laboratory ultrasonic cleaning bath. The reaction mixture was treated as described above.

Reference： [1]Rezki, Nadjet [Molecules, 2016, vol. 21, # 4]

54
2-azido-N-(6-methylbenzo[d]thiazol-2-yl)acetamide [ No CAS ]
[ 3923-52-2 ]
2-(4-(hydroxydiphenylmethyl)-1H-1,2,3-triazol-1-yl)-N-(6-methylbenzo[d]thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate In water; <i>tert</i>-butyl alcohol at 20℃; for 4h; Sonication; Inert atmosphere; regioselective reaction;	Method b: General procedure: A mixture of equimolar amounts of azidobenzothiazole 3a-c and terminal alkyne 4a-f, CuSO4 (0.01 eq) and Na-ascorbate (0.01 eq) in t-BuOH and water (1:1) was sonicated for 3-6 h at room temperature under inert atmosphere in a laboratory ultrasonic cleaning bath. The reaction mixture was treated as described above.

Reference： [1]Rezki, Nadjet [Molecules, 2016, vol. 21, # 4]

55
2-azido-N-(6-(methylsulfonyl)benzo[d]thiazol-2-yl)acetamide [ No CAS ]
[ 3923-52-2 ]
2-(4-(hydroxydiphenylmethyl)-1H-1,2,3-triazol-1-yl)-N-(6-(methylsulfonyl)benzo[d]-thiazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate In water; <i>tert</i>-butyl alcohol at 20℃; for 5h; Sonication; Inert atmosphere; regioselective reaction;	Method b: General procedure: A mixture of equimolar amounts of azidobenzothiazole 3a-c and terminal alkyne 4a-f, CuSO4 (0.01 eq) and Na-ascorbate (0.01 eq) in t-BuOH and water (1:1) was sonicated for 3-6 h at room temperature under inert atmosphere in a laboratory ultrasonic cleaning bath. The reaction mixture was treated as described above.

Reference： [1]Rezki, Nadjet [Molecules, 2016, vol. 21, # 4]

56
[ 3923-52-2 ]
[ 73183-34-3 ]
C₂₁H₂₅BO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: bis(pinacol)diborane With methanol; copper(II) bis(trifluoromethanesulfonate); 2,6-bis(pyrazole)pyridine; sodium t-butanolate In acetonitrile for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 1,1-diphenyl-2-propyn-1-ol In acetonitrile at 50℃; for 3h; Inert atmosphere; Schlenk technique; regioselective reaction;	3. General Procedure for Hydroboration of Alkynes General procedure: An oven-dried vial was charged with Cu(OTf)2 (5 mg, 0.015 mmol), LN5 (6 mg, 0.03 mmol),t-BuONa (2 mg, 0.03 mmol) and bis(pinacolato)diboron (0.9144 g, 0.36 mmol). After being sealed with a septum, the vial was connected to an argon-vacuum line and was evacuated and back filled with argon (x 3). CH3CN (2 mL) and methanol (0.9 mmol) were added and the mixture was stirred for 30 min. Then alkyne 1 (0.3 mmol) was added, the mixture usually turned to a dark brown color after addition. The mixture was stirred at 50 oC for 3h. After 3h, water were added and the aqueous phase was extracted with ethyl acetate (3 x 3 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography. Note: The carbon bearing the boron can’t be detected for all hydroboration products2in 13C NMR spectra.

Reference： [1]Liu, Shiwen; Zeng, Xiaojun; Xu, Bo [Tetrahedron Letters, 2016, vol. 57, # 33, p. 3706 - 3710]

57
[ 3923-52-2 ]
[ 605-03-8 ]
[ 3531-24-6 ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 6935 - 6942

58
[ 593-56-6 ]
[ 3923-52-2 ]
3,3-diphenyl-O-methyl-2-propenal oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 90℃; for 4h;	4.1.1 General procedure for the synthesis of compounds 2a-2i, 2m-2n General procedure: PTSA (0.06 mmol, 0.3 equiv) and NH2OH·HCl (0.24 mmol, 1.2 equiv) were successively added to a solution of propargylic alcohol (0.20 mmol, 1equiv) in DCE (1 mL). The reaction mixture was stirred at 90 °C and monitored periodically by TLC. After completion of the reaction, the mixture was cooled to room temperature, and satd aq NaHCO3 (1 mL) and CH2Cl2 (5 mL) were added. The organic layer was separated and washed successively with satd aq NaHCO3 (2×1 mL), H2O (1 mL), and brine (1 mL), then dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by flash column chromatography [silica gel, EtOAc-PE] to give the α,β-unsaturated oxime. Compound 2a13 is known compounds.

Reference： [1]Zhang, Qi; Zhang, Linjing; Tang, Chaojun; Luo, Huan; Cai, Xuediao; Chai, Yonghai [Tetrahedron, 2016, vol. 72, # 44, p. 6935 - 6942]

59
C₁₀H₆BrClO [ No CAS ]
[ 3923-52-2 ]
C₂₅H₁₆BrClO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With toluene-4-sulfonic acid In toluene at 20℃; for 6h;	1 254 mg (1.0 mmol) of the following naphthalene derivatives (4), 250 mg (1.2mmol) of the following propargyl alcohol derivatives (5) are dissolved in 30 mL of toluene, 10 mg added p-toluenesulfonic acid and it agitated at the room temperature for 6 hours. After the reaction, the solvent was removed, silica gel column chromatography refined, and it obtained output 393 mg (0.88 mmol) of white powder. Yield was 88%

Reference： [1]Current Patent Assignee: MIKI HOLDINGS CO LTD; ITOH OPTICAL INDUSTRIAL CO., LTD. - JP2015/137259, 2015, A Location in patent: Paragraph 0069-0073

60
[ 704-38-1 ]
[ 3923-52-2 ]
C₂₄H₁₈O₂S₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 15411 - 15414
Angew. Chem.,2016,vol. 128,p. 15637 - 15640,4

61
[ 2532-74-3 ]
[ 3923-52-2 ]
3a-(3,3-diphenylpropa-1,2-dien-1-yl)-8,8a-dimethyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4114 - 4117

62
[ 79544-29-9 ]
[ 3923-52-2 ]
2-fluoro-6-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8407 - 8418

63
[ 79544-29-9 ]
[ 3923-52-2 ]
4′-fluoro-3-phenylspiro[indene-1,1′-isoindolin]-3′-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8407 - 8418

64
[ 121554-10-7 ]
[ 3923-52-2 ]
5-bromo-2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8407 - 8418

65
[ 1259323-42-6 ]
[ 3923-52-2 ]
2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)-4-(trifluoromethyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;

Reference： [1]Sun, Lang; Liu, Peng; Wang, Jing; Lu, Ping; Wang, Yanguang [Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8407 - 8418]

66
[ 916792-62-6 ]
[ 3923-52-2 ]
3-fluoro-2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8407 - 8418

67
[ 916792-62-6 ]
[ 3923-52-2 ]
7′-fluoro-3-phenylspiro[indene-1,1′-isoindolin]-3′-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 8407 - 8418

68
[ 611-94-9 ]
[ 3923-52-2 ]
1-(p-methoxyphenyl)-1,4,4-triphenylbut-2-yne-1,4-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 4-Methoxybenzophenone In tetrahydrofuran at 20℃; for 22h;
71%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 4-Methoxybenzophenone In tetrahydrofuran; hexane at 20℃; for 22h;	1 General procedure for the synthesis of diols 2a-c General procedure: n-Butyllithium (2 eq, 3.85mL, 2.5M in hexane) was added dropwise to a solution of 1,1-diarylprop-2-yn-1-ol (1.00g; 4.8mmol) in dry THF (25mL) at 0°C and the cold mixture was maintained under constant stirring for 30min. The adequate benzophenone (1.1 eq) was added, at once, to the solution and the resulting mixture stirred at room temperature for 22h. The solvent was removed, HCl (5%, 30mL) was added and the aqueous phase was extracted with ethyl acetate (3×30mL). The combined organic phases were dried (Na2SO4) and the solvent removed under reduced pressure to give an oil which was purified by recrystallization from CH2Cl2/petroleum ether.

Reference： [1]Sousa, Céu M.; Berthet, Jerome; Delbaere, Stephanie; Coelho, Paulo J. [European Journal of Organic Chemistry, 2018, vol. 2018, # 25, p. 3291 - 3297]
[2]Costa, Diogo; Sousa, Céu M.; Coelho, Paulo J. [Tetrahedron, 2018, vol. 74, # 51, p. 7372 - 7379]

69
[ 90-90-4 ]
[ 3923-52-2 ]
[ 13632-69-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: (4-bromophenyl)(phenyl)methanone In tetrahydrofuran; hexane at 20℃; for 22h;	1 General procedure for the synthesis of diols 2a-c General procedure: n-Butyllithium (2 eq, 3.85mL, 2.5M in hexane) was added dropwise to a solution of 1,1-diarylprop-2-yn-1-ol (1.00g; 4.8mmol) in dry THF (25mL) at 0°C and the cold mixture was maintained under constant stirring for 30min. The adequate benzophenone (1.1 eq) was added, at once, to the solution and the resulting mixture stirred at room temperature for 22h. The solvent was removed, HCl (5%, 30mL) was added and the aqueous phase was extracted with ethyl acetate (3×30mL). The combined organic phases were dried (Na2SO4) and the solvent removed under reduced pressure to give an oil which was purified by recrystallization from CH2Cl2/petroleum ether. 4.2.1 1-(p-Bromophenyl)-1,4,4-triphenylbut-2-yne-1,4-diol (2a) Obtained from p-bromobenzophenone (1.87 g, 83%). Mp 117.3-120.1 °C. IR (KBr, cm-1): 3408, 1596, 1492, 1442, 1395, 1208, 1127, 1073, 1013, 986, 892, 818, 745, 691, 611. 1H NMR (400 MHz, CDCl3): 7.60-7.50 (m, 6H), 7.50-7.40 (m, 4H), 7.35-7.20 (m, 9H), 3.11 (s, 1H), 3.05 (s, 1H). 13C NMR (100 MHz, CDCl3): 144.5, 144.2, 143.8, 131.4, 128.4, 128.3, 128.0, 127.9, 127.8, 125.9, 125.8, 121.8, 90.3, 89.4, 74.5, 74.1. EI-MS (TOF) m/z (%): 450 (M+-18, 8), 436 (31), 434 (35), 347 (8), 276 (15), 267 (10), 265 (35), 263 (14), 207 (22), 189 (15), 184 (18), 182 (18), 178 (28), 165 (19), 105 (100). HRMS calcd for C28H19OBr (M-H2O): 450.0619, found: 450.0619.
67%	Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (4-bromophenyl)(phenyl)methanone In tetrahydrofuran at 20℃; for 22h;

Reference： [1]Costa, Diogo; Sousa, Céu M.; Coelho, Paulo J. [Tetrahedron, 2018, vol. 74, # 51, p. 7372 - 7379]
[2]Sousa, Céu M.; Berthet, Jerome; Delbaere, Stephanie; Coelho, Paulo J. [European Journal of Organic Chemistry, 2018, vol. 2018, # 25, p. 3291 - 3297]

70
[ 58452-28-1 ]
[ 28926-65-0 ]
[ 2923-28-6 ]
[ 3923-52-2 ]
[Ag₆Cu(C₂CPh₂OH)₃{HC(PPh₂)₃}₂(SO₃CF₃)₃](SO₃CF₃) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2018,vol. 2018,p. 3822 - 3828

71
[ 108534-47-0 ]
[ 3923-52-2 ]
6-((tert-butyldimethylsilyl)oxy)-2,2-diphenyl-2H-1-benzopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With toluene-4-sulfonic acid In dichloromethane at 20℃; for 4h; Inert atmosphere;	2.2 Synthesis and characterization of BP1 A 50 mL round-bottom flask was charged with 4-((tertbutyldimethylsilyl)oxy)phenol31 (0.5 g, 2.23 mmol), 1,1-diphenylprop-2-yn-1-ol (0.51 g, 2.45 mmol), a catalyticamount of p-toluenesulfonic acid (0.041 g, 0.22 mmol) andanhyd DCM (20 mL). The contents were stirred at rt undernitrogen gas atmosphere for 4 h. Subsequently, the reactionmixture was washed with a saturated Na2CO3 solution. Theorganic matter was extracted with DCM (20 mL × 3). Thecombined organic extract was dried over anhyd Na2SO4, filtered,and concentrated to dryness under vacuum. Purificationof the crude material by silica gel column chromatographyusing 5% DCM in hexane led to the product as a colorlesssolid in 77% yield (0.71 g).2.2a 6((tertButyldimethylsilyl)oxy)2,2diphenyl2H-1-benzopyran, BP1: Colorless solid; M.p. 72-74 C; IR(KBr) cm-1 3055, 2930, 2858, 1631, 1607, 1462, 1360, 1216;1H NMR(CDCl3, 400 MHz) δ 0.15 (s, 6H), 0.96 (s, 9H),6.17 (d, 1H, J = 10.1 Hz), 6.50 (d, 1H, J = 2.7 Hz), 6.54 (d,1H, J = 10.1 Hz), 6.59 (dd, 1H, J1 = 8.68 Hz, J2 = 2.8 Hz),6.77 (d, 1H, J = 8.7 Hz), 7.22-7.34 (m, 6H), 7.40-7.44 (m,4H); 13C NMR(CDCl3, 100 MHz) δ-4.5, 18.1, 25.7, 82.3,116.9, 117.5, 120.5, 121.6, 123.5, 127.0, 127.4, 128.0, 129.5,144.9, 146.7, 149.5; ESI-MS+ m/z Calcd. for C27H31O2Si415.2093 [M+H]+, found 415.2091.

Reference： [1]Mukhopadhyay, Arindam; Maka, Vijay Kumar; Moorthy, Jarugu Narasimha [Journal of Chemical Sciences, 2018, vol. 130, # 10]

72
[ 80826-37-5 ]
[ 3923-52-2 ]
6,11-dimethyl-3,3-diphenylbenzo[h]indeno[2,1-f]chromen-13(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine hydrochloride; trimethyl orthoformate In toluene at 110℃; for 8h;	Synthesis of 6,11-dimethyl-3,3-diphenylbenzo[h]indeno [2,1-f]chromen-13(3H)-one (5a) General procedure: 5-Hydroxy-3,9-dimethylbenzo[c]fluoren-7-one (4) (0.30 g, 1.10 mmol) in toluene (20 mL) was heated to 60 °C; after 30 min, an equivalent of pyridine hydrochloride (0.02 g, 0.30 mmol), trimethyl orthoformate (1.00 mL, 0.07 mmol) and 3,3-diphenylprop-2-yn-1-ol (Va) (0.25 g,1.20 mmol) were added and the mixture was heated to 110 °C for 8 h. TLC examination indicated that no starting material remained. Water (30 mL) was added and the aqueous phase extracted with ethyl acetate (3 × 30 mL). The combined organic extracts were washed with water (5 × 50 mL) and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent: petroleum ether: ethylacetate 10: 1) to afford compound 5a as a red solid; yield 0.35 g (70%); m.p. 224-225 °C; 1H NMR (400 MHz, CDCl3): δ 8.18 (d, J = 8 Hz, 1H,ArH), 8.11 (s, 1H, ArH), 7.86 (d, J = 12 Hz, 1H, ArH), 7.66 (d, J = 8 Hz,1H, ArH), 7.50 (d, J = 8 Hz, 4H, ArH), 7.33-7.36 (m, J = 8.9 Hz, 6H,ArH), 7.18 (d, J = 8 Hz, 1H, ArH), 6.32 (d, J = 9.6 Hz, 1H, ArH), 2.53(s, 3H, -CH3), 2.33(s, 3H, -CH3); 13C NMR (101MHz, CDCl3): δ 196.1,148.2, 144.7, 142.1, 138.0, 137.6, 136.0, 135.0, 134.4, 130.1, 129.6,128.2, 127.7, 126.9, 124.6, 124.4, 122.3, 122.0, 119.8, 113.6, 83.5, 22.1,20.9. Anal. calcd for C34H24O2: C, 87.90; H, 5.21; found: C, 87.92; H,5.31%.

Reference： [1]Zhao, Qian; Yang, Yanhua; Shen, Kecheng; Tao, Xian; Shen, Yingzhong [Journal of Chemical Research, 2018, vol. 42, # 9, p. 447 - 452]

73
2-azido-1-(4-(benzo[d]thiazol-2-yl)piperazin-1-yl)ethanone [ No CAS ]
[ 3923-52-2 ]
1-(4-(benzothiazol-2-yl)piperazin-1-yl)-2-(4-(hydroxydiphenylmethyl)-1H-1,2,3-triazol-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(II) sulfate; sodium L-ascorbate In water; dimethyl sulfoxide at 80℃; for 8h;	3.1.11. General Procedure for the Synthesis of 1,4-Disubstituted 1,2,3-triazoles (5a-l) General procedure: A solution of copper sulfate (0.8 mmol) and sodium ascorbate (1.1 mmol) in water (10 mL) wasadded with stirring to a mixture of the appropriate alkyne 4a-l (1 mmol) and benzothiazoleazide3 (1 mmol) in DMSO (10 mL). Then, the reaction mixture was heated at 80 °C for 8 h, until theconsumption of the starting material as indicated by TLC. The reaction mixture was quenched withice water and the solid thus formed was collected by filtration, washed with saturated solution ofammonium chloride and recrystallized from ethanol to give the desired 1,2,3-triazoles 5a-l.

Reference： [1]Aouad, Mohamed R.; Soliman, Moataz A.; Alharbi, Muath O.; Bardaweel, Sanaa K.; Sahu, Pramod K.; Ali, Adeeb A.; Messali, Mouslim; Rezki, Nadjet; Al-Soud, Yaseen A. [Molecules, 2018, vol. 23, # 11]

74
[ 3923-52-2 ]
[ 502161-03-7 ]
C₃₃H₂₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; at 20℃; for 20h;Reflux; Inert atmosphere;	In a 100 mL three-necked flask purged with nitrogen, 3.30 g of <strong>[502161-03-7]3-iodo-9-phenylcarbazole</strong>,1.86 g of 1,1-diphenyl-2-propyn-1-ol,0.025 g of triphenylphosphine,Bis (triphenylphosphine) palladium (II) dichloride0.0125 g, 0.0125 g of CuI (I)And 40 mL of triethylamine were added,The mixture was heated to reflux for 4 hours,Further stirring was continued at room temperature for 16 hours for reaction.After completion of the reaction, the reaction solution was neutralized with 5% hydrochloric acid aqueous solution,The organic phase was extracted with ethyl acetate,The obtained extract was dried using anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was dissolved in ethanolRecrystallization was carried out to obtain 2.0 g (yield: 50%) of white crystals. Identification of the obtained white crystals was carried out by 1 H-NMR (see FIG. 7) and MS,The purity is 99% or more(LC, Area%).Based on the above analysis results,White crystals could be identified as compounds of formula (1f).

Reference： [1]Patent: JP5821662,2015,B2 .Location in patent: Paragraph 0017; 0085; 0087

75
[ 1762-84-1 ]
[ 3923-52-2 ]
C₃₃H₂₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 20h; Reflux; Inert atmosphere;	9 Example 9 In a 100 mL three-necked flask purged with nitrogen,4-bromo-p-terphenyl2.76 g,1.86 g of 1,1-diphenyl-2-propyn-1-ol,0.025 g of triphenylphosphine,0.0125 g of bis (triphenylphosphine) palladium (II) dichloride,0.0125 g of CuI (I)And 40 mL of triethylamine were added,The mixture was heated to reflux for 4 hours,Further stirring was continued at room temperature for 16 hours for reaction.After completion of the reaction, the reaction solution was neutralized with 5% hydrochloric acid aqueous solution,The organic phase was extracted with ethyl acetate,It was dried with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was recrystallized from toluene to obtain 0.77 g (yield 20%) of white crystals.Identification of the obtained white crystals was confirmed by 1 H-NMR (FIG. 10) and MS, and the purity was 88% (LC, Area%).Based on the above analysis results, the white crystal could be identified as the compound of formula (1i).

Reference： [1]Current Patent Assignee: DEXERIALS CORPORATION - JP5821662, 2015, B2 Location in patent: Paragraph 0096; 0099

76
C₁₉H₁₅FO [ No CAS ]
[ 3923-52-2 ]
C₃₄H₂₅FO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With para-dodecylbenzenesulfonic acid In toluene at 40℃; for 6h;	1 Synthesis of Ia (R5=F, R6=R7=CH3), the reaction formula is as follows: Add 186 mg (0.67 mmol) to a 25 mL round bottom flaskM5a (R5=F, R7=R8=CH3),139 mg (0.67 mmol) of 1,1-diphenyl-2-propyn-1-ol and10mL toluene,Add 1-2 drops of dodecylbenzenesulfonic acid,Observe the discoloration of the solution. Stir at 40 ° C for 6 h (TLC monitoring), concentrate,Recrystallization of petroleum ether / dichloromethane. Yield: 72%

Reference： [1]Current Patent Assignee: TIANJIN UVOS TECH - CN108623554, 2018, A Location in patent: Paragraph 0049; 0062-0064

77
9,9-bis(6-hydroxynaphthalen-2-yl)fluorene [ No CAS ]
[ 3923-52-2 ]
C₆₃H₄₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.2%	With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere;	1-2 Example 1-2 To a 1,000-mL three-neck flask equipped with a thermometer, a condenser and a magnetic stirrer were added 10 g of bisnaphthol fluorene, 239 g of dichloroethane, 14.1 g of trimethyl orthoformate and 13.9 g of 1,1-diphenyl-2-propyne-1-ol in a nitrogen atmosphere, and dissolution was attained at 80° C. To the resulting solution, 3.35 g of pyridinium p-toluenesulfonate was added and then a reaction was allowed at 80° C. for 16 hrs. After the completion of the reaction, the reaction solution was washed twice with water, and an organic layer thus obtained was concentrated to 72 g. The concentrate was charged into 360 g of methanol to permit reprecipitation. The precipitate thus obtained was dried under reduced pressure at 60° C. to give the compound (A-2) (amount: 14.8 g; yield: 80.2%).

Reference： [1]Current Patent Assignee: JSR CORPORATION - US2019/94695, 2019, A1 Location in patent: Paragraph 0196

78
ruthenium(III) chloride trihydrate [ No CAS ]
[ 3923-52-2 ]
[ 2622-14-2 ]
[ 250220-36-1 ]

Yield	Reaction Conditions	Operation in experiment
94%		A mixture of ruthenium(III)chloride hydrate (8.05 g ≈0.03 mol) and triphenylphosphane (39.3 g, 0.15 mol) wasplaced in a Schlenk flask, which was purged with argon. Methanol (300 mL) wasadded into the flask and the resulting mixture was heated at reflux for 4 h undercontinuous stirring. After cooling of the reaction mixture to rt, the precipitate wasfiltered off, washed with Et2O (3 × 100 mL) and air-dried to give 30.93 g of theWilkinson complex as black powder.Dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphane)ruthenate(8). A solution of RuCl2(PPh3)3-4 (40.0 g, ≈41.7 mmol) and 1,1-diphenyl-2-propyn-1-ol(10.4 g, 50.1 mmol) in abs. THF (300 mL) was placed into a Schlenk flask under anargon atmosphere. A 5.4 M solution of HCl in dioxane (6.2 mL, 33.4 mmol) wasadded and then the mixture was heated at reflux for 30 min under continuous stirringand an argon atmosphere. After cooling to rt, around 50% of mixture volume wasevaporated under reduced pressure. Acetone (280 mL) and tricyclohexylphosphane25.7 g (91.9 mmol) were added to the residue and the resulting suspension wasstirred until thickening (≈0.5 h). After holding at -20 for 10 h the precipitate wasfiltered off and washed sequentially by methanol (2 × 80 mL), acetone (2 × 100 mL)and hexane (100 mL), then dried under vacuum at rt to give indenylidene-rutheniumcomplex 8 in 94% yield (36.3 g, 39.2 mmol) as red-brown powder.Complex 8 can be obtained by an analogical procedure in 90% yield (34.8 g)using absolute dioxane as a solvent instead absolute THF.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 769 - 779

79
[ 51738-07-9 ]
[ 3923-52-2 ]
3-(benzyloxy)-4-chloro-2-(diphenylmethylene)-2,3-dihydro-1H-inden-1-one [ No CAS ]