[ CAS No. 1896-62-4 ] {[proInfo.proName]}

Name: 1896-62-4|(E)-4-Phenylbut-3-en-2-one|98%
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Quality Control of [ 1896-62-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1896-62-4 ]

CAS No. :	1896-62-4	MDL No. :
Formula :	C₁₀H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BWHOZHOGCMHOBV-BQYQJAHWSA-N
M.W :	146.19	Pubchem ID :	637759
Synonyms :	trans-Benzalacetone;Trans-4-Phenyl-3-buten-2-one

Safety of [ 1896-62-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1896-62-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1896-62-4 ]
Downstream synthetic route of [ 1896-62-4 ]

[ 1896-62-4 ] Synthesis Path-Upstream 1~3

1
[ 75-36-5 ]
[ 174279-17-5 ]
[ 2142-76-9 ]
[ 119873-74-4 ]
[ 1896-62-4 ]

Reference： [1] Tetrahedron, 1996, vol. 52, # 3, p. 861 - 868

2
[ 383-63-1 ]
[ 1896-62-4 ]
[ 18931-64-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 40℃; for 3 h;	EXAMPLE 4 1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-5-styryl-3-trifluoromethyl-1H-pyrazole 1,1,1-Trifluoro-6-phenylhex-5-ene-2,4-dione. Sodium hydride (547 mg, 60percent dispersion in mineral oil, 13.68 mmol) was added to ethyl trifluoroacetate (1.63 mL, 13.68 mmol). (Note: Carefulness is required. The reaction caught fire upon adding sodium hydride to ethyl trifluoroacetate.) Trans-4-Phenyl-3-buten-2-one (1 g, 6.84 mmol) was added, and the reaction was stirred for 3 hours at 40° C. The reaction was cooled to room temperature and quenched with water, then diluted with 1 N HCl. The mixture was extracted with ethyl acetate, dried over MgSO₄, and concentrated. The reaction was assumed to be quantitative. LC-MS (C₁₂H₉F₃O₂ calculated 242) m/z 243 (M+H).

Reference： [1] Patent: US2007/197526, 2007, A1, . Location in patent: Page/Page column 10
[2] Russian Chemical Bulletin, 1996, vol. 45, # 9, p. 2169 - 2171

3
[ 407-38-5 ]
[ 1896-62-4 ]
[ 18931-64-1 ]

Reference： [1] Organic Syntheses, 1996, vol. 73, p. 134 - 134

[ 1896-62-4 ] Synthesis Path-Downstream 1~88

1
[ 952-92-1 ]
[ 1896-62-4 ]
2-Benzyl-7-hydroxy-7-methyl-5-phenyl-2,4a,5,6,7,8-hexahydro-pyrido[3,4-c]azepin-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38 % Turnov.	With tris(2,2'-bipyridyl)ruthenium dichloride In methanol Irradiation;

Reference： [1]Pac,C.; Ihama,M.; Yasuda,M. [Journal of the American Chemical Society, 1981, vol. 103, p. 6495]

2
[ 591-50-4 ]
[ 78-94-4 ]
[ 1896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In N,N-dimethyl-formamide at 100℃; for 18h;	4.4. General procedure of the Heck coupling reactions of iodobenzene with styrene General procedure: In a 100 mL two-necked flask, the mixture of iodobenzene (2 mmol), styrene (3 mmol), NEt3 (4 mmol), and the nano-catalyst solution (4.5×10-4 mmol) were added in methanol (4 mL). The flask was sealed and the mixture was allowed to stir in a preheated oil bath at 100 °C for the appropriate time. The reactions were monitored by thin layer chromatography (TLC). After the reaction was completed, the reaction mixture was then cooled at room temperature. The solid nano-catalyst was separated by centrifuge and washed with water to remove base and salt. The remaining solution was then washed with acetone to remove adsorbed organic substrate. Finally, the prepared samples were analyzed by GC.
98%	With tetrabutyl-ammonium chloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 48h;
97%	With triphenylphosphine on reverse phase silica; triethylamine In methanol; water

91%	With sodium acetate In N,N-dimethyl-formamide at 110℃; for 20h;
91%	With [Pd(C₃H₅)Cl]2 cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane complex; sodium acetate; hydroquinone In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; regioselective reaction;
74%	With triethylamine In N,N-dimethyl-formamide at 90℃; for 16h;	2.2. General procedure for the Heck reaction General procedure: To a round-bottom flask catalyst 1a (0.1 mol%, 1 mg), alkene(1.5 mmol), aryliodide (1 mmol), triethylamine (2 mmol) andDMF/H2O (4 mL + 1 mL) were added. The reaction mixture was heated at 90C for 21 h. Then, the reaction mixture was cooled at room temperature, diluted with water and extracted withdichloromethane. The organic phase is evaporated under reducedpressure and the residue purified with a short plug of silica undervacuum using petroleum ether/ethyl acetate as eluent.
30 % Chromat.	With C₆H₃(CH₂PiPr₂)2(palladium(II)(trifluoroacetate); sodium carbonate In various solvent(s) at 140℃; for 40h;
54 % Spectr.	With triethylamine In N,N-dimethyl-formamide at 100℃; for 3h;
90 % Chromat.	With triethylamine In acetonitrile for 30h; Heating;
	With triethylamine In acetonitrile for 48h; Heating;
76 % Spectr.	With triethylamine In acetonitrile at 100℃; for 12h;
	With sodium acetate In N,N-dimethyl-formamide at 130℃; for 24h;

Reference： [1]Location in patent: experimental part Heshmatpour, Felora; Abazari, Reza; Balalaie, Saeed [Tetrahedron, 2012, vol. 68, # 14, p. 3001 - 3011]
[2]Jeffery, Tuyet [Journal of the Chemical Society. Chemical communications, 1984, # 19, p. 1287 - 1289]
[3]Anson, Michael S.; Mirza, Amin R.; Tonks, Louise; Williams, Jonathan M.J. [Tetrahedron Letters, 1999, vol. 40, # 39, p. 7147 - 7150]
[4]Lemhadri, Mhamed; Doucet, Henri; Santelli, Maurice [Synlett, 2006, # 18, p. 2935 - 2940]
[5]Location in patent: experimental part Lemhadri, Mhamed; Fall, Yacoub; Doucet, Henri; Santelli, Maurice [Synthesis, 2009, # 6, p. 1021 - 1035]
[6]Pavia, Cinzia; Giacalone, Francesco; Bivona, Lucia Anna; Salvo, Anna Maria Pia; Petrucci, Chiara; Strappaveccia, Giacomo; Vaccaro, Luigi; Aprile, Carmela; Gruttadauria, Michelangelo [Journal of Molecular Catalysis A: Chemical, 2014, vol. 387, p. 57 - 62]
[7]Ohff; Ohff; Van der Boom; Milstein [Journal of the American Chemical Society, 1997, vol. 119, # 48, p. 11687 - 11688]
[8]Yang, Dan; Chen, Ying-Chun; Zhu, Nian-Yong [Organic Letters, 2004, vol. 6, # 10, p. 1577 - 1580]
[9]Martínez, Sandra; Vallribera, Adelina; Cotet, Cosmin L.; Popovici, Mihaela; Martín, Laura; Roig, Anna; Moreno-Mañas, Marcial; Molins, Elies [New Journal of Chemistry, 2005, vol. 29, # 10, p. 1342 - 1345]
[10]Martinez, Sandra; Moreno-Manas, Marcial; Vallribera, Adelina; Schubert, Ulrich; Roig, Anna; Molins, Elies [New Journal of Chemistry, 2006, vol. 30, # 7, p. 1093 - 1097]
[11]Arisawa, Mitsuhiro; Hamada, Masahiro; Takamiya, Ikuko; Shimoda, Masahiko; Tsukamoto, Shiro; Arakawa, Yasuhiko; Nishida, Atsushi [Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1063 - 1070]
[12]Location in patent: experimental part Ghiaci, Mehran; Valikhani, Donya; Sadeghi, Zahra [Chinese Chemical Letters, 2012, vol. 23, # 8, p. 887 - 890]

3
[ 329-98-6 ]
[ 598-31-2 ]
[ 1896-62-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1992,p. 435 - 439

4
[ 6651-36-1 ]
[ 1896-62-4 ]
[ 221363-48-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at -78℃; for 3h;
93%	In dichloromethane at -78℃; for 13h;
85%	With lithium perchlorate In nitromethane for 16h; Ambient temperature;

With hydrogenchloride; bismuth(III) chloride 1) CH₂Cl₂, rt, 6 h, 2) MeOH; Yield given. Multistep reaction;

Reference： [1]Hayashi, Masaji; Inubushi, Atsuro; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 11, p. 4037 - 4042]
[2]Iwasawa, Nobuharu; Mukaiyama, Teruaki [Chemistry Letters, 1987, p. 463 - 466]
[3]Sankararaman; Sudha [Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 2155 - 2157]
[4]Wada, Makoto; Takeichi, Eiji; Matsumoto, Takashi [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 3, p. 990 - 994]

5
[ 32884-23-4 ]
[ 1896-62-4 ]
[ 75335-18-1 ]

Reference： [1]Liebigs Annalen der Chemie,1980,p. 1283 - 1295

6
[ 622-50-4 ]
[ 1896-62-4 ]
[ 273754-94-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrabutyl-ammonium chloride; sodium acetate In N,N-dimethyl-formamide at 60℃; for 3.5h;

Reference： [1]Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; et al. [Tetrahedron, 1989, vol. 45, # 3, p. 813 - 828]

7
[ 50472-20-3 ]
[ 1896-62-4 ]
2-Methyl-4-phenyl-azuleno[2,1-b]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 1309 - 1314

8
[ 42861-71-2 ]
[ 1896-62-4 ]
Acetic acid 3-((E)-3-oxo-1-phenyl-but-1-enyl)-phenyl ester [ No CAS ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 813 - 828

9
[ 124946-37-8 ]
[ 1896-62-4 ]
[ 814-29-9 ]
[ 129410-83-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 435 - 440

10
[ 55244-11-6 ]
[ 1896-62-4 ]
[ 18631-33-9 ]

Reference： [1]Archiv der Pharmazie,1994,vol. 327,p. 33 - 40

11
[ 1817-57-8 ]
[ 1896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C₁₉H₁₃I₂N₃O₂Ru; hydrogen In water at 80℃; for 4h; Autoclave; Schlenk technique; chemoselective reaction;
89%	With formic acid; gold nanoparticles on rutile titania; triethylamine In acetone at 60℃; for 1h; stereoselective reaction;
	With TPPMS (meta-monosulfonated triphenylphosphane, Na salt); water for 3h;

	Multi-step reaction with 2 steps 1: Lindlar reduction 2: 98 percent / cuprate induced isomerization
	Multi-step reaction with 2 steps 1: Lindlar reduction 2: tetrahydrofuran / -95 °C
	With formic acid; C₆₆H₇₂P₃Pd₃S₃⁽¹⁺⁾*F₆Sb^(1-); triethylamine In tetrahydrofuran for 4h; Schlenk technique; Inert atmosphere; Reflux; stereoselective reaction;
	With Chr-OYE₁ (old yellow enzyme from chryseobacterium sp. CA₄₉); β-nicotinamide adenine dinucleotide reduced In aq. phosphate buffer at 30℃; for 0.0333333h; Enzymatic reaction;	2.5 Bioreduction of activated alkenes and product analysis General procedure: The bioreduction of various substrates was performed in 1-ml reaction system containing 100mM potassium phosphate buffer (pH 7.0), 10mM NADH, 5mM substrate, and 50μg purified Chr-OYE1 or 500μg purified Chr-OYE2. After 2-min or 16-h incubation at 30°C for Chr-OYE1 and Chr-OYE2, respectively, the reactions were terminated by extraction with ethyl acetate. The organic phase was analyzed using GC or HPLC. (0013) Preparative-scale biotransformation was performed in 30-ml reaction system for substrates 4a, 6a, and 12a-17a catalyzed with Chr-OYE1. The incubation was continued for 12h. The extracted organic phase was combined and concentrated under reduced pressure. The final product was purified with column chromatography and subjected to GC or HPLC analysis, as well as NMR analysis to confirm the structure and purity.
98 % de	With Pd₃Pb/SiO₂; RhSb/SiO₂; hydrogen In tetrahydrofuran at 25℃; for 1.7h;
9.8 mg	With water; triphenylphosphine; benzoic acid In tetrahydrofuran at 65℃; for 24h; diastereoselective reaction;
99 %Chromat.	With formic acid; C₂₅H₂₃ClN₂Pd; triethylamine; triphenylphosphine In water; acetonitrile at 70℃; for 4h; Inert atmosphere;

Reference： [1]Bera, Jitendra K.; Choudhury, Joyanta; Das, Shubhajit; Dutta, Indranil; Pati, Swapan K.; Saha, Sayantani; Yadav, Suman [Organometallics, 2020, vol. 39, # 17, p. 3212 - 3223]
[2]Li, Shu-Shuang; Tao, Lei; Wang, Fu-Ze-Rong; Liu, Yong-Mei; Cao, Yong [Advanced Synthesis and Catalysis, 2016, vol. 358, # 9, p. 1410 - 1416]
[3]Larpent, Chantal; Meignan, Gerard [Tetrahedron Letters, 1993, vol. 34, # 27, p. 4331 - 4334]
[4]Corey, E. J.; Boaz, Neil W. [Tetrahedron Letters, 1985, vol. 26, # 49, p. 6015 - 6018]
[5]Corey, E. J.; Boaz, Neil W. [Tetrahedron Letters, 1985, vol. 26, # 49, p. 6015 - 6018]
[6]Deyris, Pierre-Alexandre; Cañeque, Tatiana; Wang, Yanlan; Retailleau, Pascal; Bigi, Franca; Maggi, Raimondo; Maestri, Giovanni; Malacria, Max [ChemCatChem, 2015, vol. 7, # 20, p. 3266 - 3269]
[7]Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 123, p. 91 - 99]
[8]Furukawa, Shinya; Komatsu, Takayuki [ACS Catalysis, 2016, vol. 6, # 3, p. 2121 - 2125]
[9]Pierce, Brett M.; Simpson, Brittany F.; Ferguson, Kane H.; Whittaker, Rachel E. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6659 - 6662]
[10]Mizuno, Takahiro; Murai, Toshiaki; Shibahara, Fumitoshi; Shibata, Yoshifuru [Bulletin of the Chemical Society of Japan, 2020, vol. 93, # 3, p. 332 - 337]

12
[ 75-36-5 ]
[ 174279-17-5 ]
[ 2142-76-9 ]
[ 119873-74-4 ]
[ 1896-62-4 ]
2,6-(dimethylphenyl)hydroxydimethylsilane [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 861 - 868

13
[ 50-00-0 ]
[ 142-64-3 ]
[ 1896-62-4 ]
1<i>t</i>,1'<i>t</i>-diphenyl-5,5'-piperazine-1,4-diyl-bis-pent-1-en-3-one; dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4012 - 4020

14
[ 344-14-9 ]
[ 1896-62-4 ]
[ 370-07-0 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 7525 - 7528

15
[ 383-63-1 ]
[ 1896-62-4 ]
[ 18931-64-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride; at 40℃; for 3h;	EXAMPLE 4 1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-5-styryl-3-trifluoromethyl-1H-pyrazole 1,1,1-Trifluoro-6-phenylhex-5-ene-2,4-dione. Sodium hydride (547 mg, 60% dispersion in mineral oil, 13.68 mmol) was added to ethyl trifluoroacetate (1.63 mL, 13.68 mmol). (Note: Carefulness is required. The reaction caught fire upon adding sodium hydride to ethyl trifluoroacetate.) Trans-4-Phenyl-3-buten-2-one (1 g, 6.84 mmol) was added, and the reaction was stirred for 3 hours at 40 C. The reaction was cooled to room temperature and quenched with water, then diluted with 1 N HCl. The mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated. The reaction was assumed to be quantitative. LC-MS (C12H9F3O2 calculated 242) m/z 243 (M+H).

Reference： [1]Patent: US2007/197526,2007,A1 .Location in patent: Page/Page column 10
[2]Russian Chemical Bulletin,1996,vol. 45,p. 2169 - 2171

16
[ 17881-88-8 ]
[ 78-94-4 ]
[ 1896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	With palladium diacetate
47%	In 1,2-dimethoxyethane at 60℃; for 13h;

Reference： [1]Hirabayashi, Kazunori; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro [Tetrahedron Letters, 1998, vol. 39, # 43, p. 7893 - 7896]
[2]Hirabayashi, Kazunori; Ando, Jun-Ichi; Kawashima, Jun; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 6, p. 1409 - 1417]

17
[ 52784-31-3 ]
[ 1896-62-4 ]

Reference： [1]Canadian Journal of Chemistry,1999,vol. 77,p. 1009 - 1034

18
[ 100-52-7 ]
[ 1896-62-4 ]
[ 35225-79-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide In methanol
83%	With sulfuric acid In ethanol at 20℃;	4.1.3.2 Synthesis of MACs 1-3 and 5-8 General procedure: To a solution of benzylideneacetone (1) (5.2 mmol) in EtOH (10 mL) was added the respective benzaldehyde derivative (5.0 mmol). Catalytic amounts of H2SO4 were added to the reaction mixture, and the solution was stirred at room temperature for 24-48h. Reaction medium was poured onto crushed ice. The crude product was partitioned with ethyl acetate (3×25 mL), and the combined organic phase was concentrated under reduced pressure. MACs 1, 6 and 8 were purified by gel filtration column chromatography (LH-20) using EtOH as eluent. MAC 2 was recrystallized in EtOH. MACs 3, 5 and 7 were purified by column chromatography over silica gel using mixtures of hexane and ethyl acetate (4:1), (9:1) and (9:1) as mobile phases, respectively.
78%	With sodium hydroxide In ethanol at 20℃;

77%	With lithium hydroxide monohydrate In ethanol at 20℃; for 72h;	Preparation of (1E,4E)-1,5-diarylpenta-1,4-dien-3-ones General procedure: A solution of 2 g 4-phenylbut-3-en-2-one (13.68 mmol, 1 equiv.) and 0.1 g LiOH.H2O in 20 mL ethanol was stirred at room temperature for 10 minutes. Afterward, an appropriately substituted benzaldehyde (13.68 mmol, 1 equiv.) was added drop-wise (or portion-wise). The solution was stirred at room temperature or 40°C for 3 days. The resulting slurry was filtered; the residue was washed with EtOH and water, and finally recrystallized from EtOH.
	With sodium hydroxide In ethanol; water at 20℃;
	With potassium hydroxide In methanol; water at 0℃;	Synthesis of (E)-chalcones 1n-q General procedure: In a 10 mL flask at 0 °C was added a 5:1 MeOH-H2O mixture (6 mL), 85% KOH aqueous solution and benzaldehyde (6 mmol, 1.2 eq). Then acetophenone (5 mmol) was added dropwise over a period of 10 min. The reaction mixture was stirred for 5-48 hours at 0 °C and then quenched with an aqueous solution of NH4Cl (20 mL), extracted with AcOEt (4 x 30 mL). The organic phase was dried over Na2SO4 and then concentrated.
	With sodium hydroxide In ethanol; water at 20℃;

Reference： [1]Bhaskar Reddy; Somasekhar Reddy; Subba Reddy [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 12, p. 1342 - 1348]
[2]Polaquini, Carlos R.; Marques, Beatriz C.; Ayusso, Gabriela M.; Morão, Luana G.; Sardi, Janaína C.O.; Campos, Débora L.; Silva, Isabel C.; Cavalca, Lúcia B.; Scheffers, Dirk-Jan; Rosalen, Pedro L.; Pavan, Fernando R.; Ferreira, Henrique; Regasini, Luis O. [Bioorganic Chemistry, 2021, vol. 109]
[3]Li, Pei-Ze; Liu, Zai-Qun [Medicinal Chemistry Research, 2014, vol. 23, # 7, p. 3478 - 3490]
[4]Roman, Bart I.; De Ryck, Tine; Verhasselt, Sigrid; Bracke, Marc E.; Stevens, Christian V. [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 5, p. 1027 - 1031]
[5]Rocchi, Damiano; González, Juan F.; Gómez-Carpintero, Jorge; González-Ruiz, Víctor; Martín, M. Antonia; Sridharan, Vellaisamy; Menéndez, J. Carlos [ACS Combinatorial Science, 2018, vol. 20, # 12, p. 722 - 731]
[6]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]
[7]Zhuang, Hongfeng; Lu, Nan; Ji, Na; Han, Feng; Miao, Chengxia [Advanced Synthesis and Catalysis, 2021, vol. 363, # 24, p. 5461 - 5472]

19
[ 41252-97-5 ]
[ 1896-62-4 ]
4-(4-methyl-3-nitro-phenyl)-4-phenyl-butan-2-one [ No CAS ]

Reference： [1]Synlett,2000,p. 650 - 652

20
[ 78-94-4 ]
[ 791-31-1 ]
[ 1896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	In 1,2-dimethoxyethane at 60℃; for 13h;

Reference： [1]Hirabayashi, Kazunori; Ando, Jun-Ichi; Kawashima, Jun; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 6, p. 1409 - 1417]

21
[ 6746-22-1 ]
[ 1896-62-4 ]
[ 613-33-2 ]
[ 80331-24-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 2149 - 2155

22
[ 58068-80-7 ]
[ 1896-62-4 ]
(1E,3Z)-1-phenyl-3-methyldeca-1,3-diene [ No CAS ]
(1E,3E)-3-methyl-1-phenyl-1,3-decadiene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 3104 - 3108

23
[ 2551-83-9 ]
[ 1896-62-4 ]
[ 100840-12-8 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 6536 - 6537

24
[ 42998-51-6 ]
[ 1896-62-4 ]
2-((S)-3-Oxo-1-phenyl-butyl)-malonic acid benzyl ester ethyl ester [ No CAS ]
2-((R)-3-Oxo-1-phenyl-butyl)-malonic acid benzyl ester ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (4S,2R/S)-4-benzyl-1-methylimidazolidine-2-carboxylic acid at 20℃; for 150h; Title compound not separated from byproducts;

Reference： [1]Halland, Nis; Aburel, Pompiliu S.; Jorgensen, Karl Anker [Angewandte Chemie - International Edition, 2003, vol. 42, # 6, p. 661 - 665]

25
[ 52267-39-7 ]
[ 1896-62-4 ]
2-((R)-3-Oxo-1-phenyl-butyl)-malonic acid benzyl ester methyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 661 - 665

26
[ 2051-90-3 ]
[ 1896-62-4 ]
trans-1-acetyl-2,2,3-triphenylcyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With tetrabutylammomium bromide; copper(I) bromide In pyridine; N,N-dimethyl-formamide at -10 - -5℃; Electrochemical reaction;

Reference： [1]Oudeyer, Sylvain; Léonel, Eric; Paugam, Jean Paul; Nédélec, Jean-Yves [Tetrahedron, 2003, vol. 59, # 7, p. 1073 - 1081]

27
[ 13515-95-2 ]
[ 1896-62-4 ]
[ 232589-57-0 ]
(S)-2-[3-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-1-methyl-3-phenyl-propylamino]-6-amino-hexanoic acid [ No CAS ]

Reference： [1]Journal of Carbohydrate Chemistry,2003,vol. 22,p. 781 - 800

28
[ 94465-25-5 ]
[ 1896-62-4 ]
[ 76217-07-7 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 6942 - 6944

29
[ 13141-38-3 ]
[ 1896-62-4 ]
4-phenyl-4-(2-phenyl-1H-indol-3-yl)butan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tetrachloroaurate dihydrate In ethanol at 30℃; for 2.5h;
75%	With palladium dichloride In acetonitrile at 60℃; for 48h; Inert atmosphere;	3.18 General experimental procedure for the synthesis of 2,3-disubstituted indoles General procedure: The substituted 2-alkynylaniline (1.0 mmol) was dissolved in acetonitrile (5.0 mL) and stirred until the solution became homogeneous. To this solution, methyl vinyl ketone (1.5 mmol) followed by 20 mol % of PdCl2 (59-60%, 35 mg) was added under a nitrogen atmosphere, then heated to 60 °C and monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and the acetonitrile was removed by vacuum evaporation. The resulting crude product was purified by column chromatography to afford the desired 2,3-disubstituted indoles. 4-Phenyl-4-(2-phenyl-1H-indol-3-yl)butan-2-one (3r) Colorless solid; Yield: (237 mg, 75%); mp: 123-125 °C; FT-IR (KBr): ν/cm-1 3401, 1680; 1H NMR (400 MHz, CDCl3) δH (ppm): 8.14 (br s, 1H), 7.61 (d, J=8 Hz, 1H), 7.54-7.52 (m, 2H), 7.47-7.33 (m, 6H), 7.29-7.26 (m, 2H), 7.21-7.17 (m, 2H), 7.12-7.09 (m, 1H), 5.08 (t, J=7.3 Hz, 1H), 3.49-3.34 (m, 2H),1.97 (s, 3H). 13C NMR (100 MHz, CDCl3) δC (ppm): 207.7, 144.6, 136.4, 135.9, 133.1, 129.0, 128.9, 128.6, 128.3, 127.8, 127.6, 126.2, 122.2, 120.8, 119.9, 114.1, 111.4, 49.5, 37.2, 30.5. LRMS (EI) (m/z) (relative intensity): 339 (M+, 50), 282 (100), 204 (85), 78 (80); HRMS calcd for C24H21O1N1 (M+): 339.1614, found 339.1623.

Reference： [1]Alfonsi, Maria; Arcadi, Antonio; Aschi, Massimiliano; Bianchi, Gabriele; Marinelli, Fabio [Journal of Organic Chemistry, 2005, vol. 70, # 6, p. 2265 - 2273]
[2]Janreddy, Donala; Kavala, Veerababurao; Kuo, Chun-Wei; Kuo, Ting-Shen; He, Chiu-Hui; Yao, Ching-Fa [Tetrahedron, 2013, vol. 69, # 15, p. 3323 - 3330]

30
[ 6742-26-3 ]
[ 1896-62-4 ]
methyl 1-oxo-2-(1-phenyl-3-oxobutyl)indan-2-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 13096 - 13097

31
[ 2001-45-8 ]
[ 78-94-4 ]
[ 1896-62-4 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6166 - 6169

32
[ 63922-69-0 ]
[ 1896-62-4 ]
(1Z,3E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene [ No CAS ]
(E,E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2006,vol. 181,p. 2283 - 2295

33
[ 19125-34-9 ]
[ 1896-62-4 ]
6-hydroxy-6-methyl-3,8-diphenyl-3-azabicyclo[3.3.1]nonan-9-one [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 2865 - 2874

34
[ 1465-76-5 ]
[ 1896-62-4 ]
2-(tert-butyl)-4-(3-oxo-1-phenylbutyl)-8-phenyl-1,3,4,7,8,8a-hexahydro-6(2H)-isoquinoline [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 2865 - 2874

35
[ 34801-09-7 ]
[ 1896-62-4 ]
N-(2-[(2E)-1-methyl-3-phenyl-2-propen-1-yl]amino}phenyl)acetamide [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 3029 - 3039

36
[ 4139-61-1 ]
[ 1896-62-4 ]
6-bromo-4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 413 - 415

37
[ 2033-24-1 ]
[ 50670-58-1 ]
[ 1896-62-4 ]
(7β,11β)-7-(4'-bromobiphenyl-4-yl)-3,3-dimethyl-11-phenyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7120 - 7124

38
[ 14447-18-8 ]
[ 100-52-7 ]
[ 1896-62-4 ]
[ 1017571-91-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. XX719-726

39
[ 5034-06-0 ]
[ 1896-62-4 ]
[ 196609-07-1 ]
[ 212066-31-4 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 13410 - 13411

40
[ 496-64-0 ]
[ 1896-62-4 ]
8-acetyl-4-hydroxy-7-phenyl-2-oxabicyclo[2.2.2]oct-5-en-3-one [ No CAS ]
8-acetyl-4-hydroxy-7-phenyl-2-oxabicyclo[2.2.2]oct-5-en-3-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2422 - 2423

41
[ 496-64-0 ]
[ 1896-62-4 ]
8-acetyl-4-hydroxy-7-phenyl-2-oxabicyclo[2.2.2]oct-5-en-3-one [ No CAS ]
8-acetyl-4-hydroxy-7-phenyl-2-oxabicyclo[2.2.2]oct-5-en-3-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 2422 - 2423

42
[ 1896-62-4 ]
[ 22031-64-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With ammonia; iodine In water at 60℃; for 2h;

Reference： [1]Cao, Liping; Ding, Jiaoyang; Gao, Meng; Wang, Zihua; Li, Juan; Wu, Anxin [Organic Letters, 2009, vol. 11, # 17, p. 3810 - 3813]

43
[ 1184731-39-2 ]
[ 109-60-4 ]
[ 2315-68-6 ]
[ 1896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 57 %Spectr. 2: 56% 3: 22%	With propan-1-ol; (triphenylphosphine)gold(I) chloride; oxygen; silver(I) triflimide In dichloromethane at 25℃; for 24h;

Reference： [1]Location in patent: scheme or table Das, Arindam; Chaudhuri, Rupsha; Liu, Rai-Shung [Chemical Communications, 2009, # 27, p. 4046 - 4048]

44
[ 2169-69-9 ]
[ 1896-62-4 ]
[ 1195790-88-5 ]
ethyl (2S,6R)-1-cyano-4-oxo-2,6-diphenylcyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

45
[ 606-23-5 ]
[ 10111-08-7 ]
[ 1896-62-4 ]
(2β,6β)-2-(1H-imidazol-2-yl)-6-phenylspiro[cyclohexane-1,2'-indene]-1',3',4-trione [ No CAS ]