Name: 625-33-2|Pent-3-en-2-one|97%
Brand: Ambeed
SKU: A458462
Price: 6.0 USD
Availability: InStock
Rating: 93 (26 reviews)

1
[ 625-33-2 ]
[ 6032-29-7 ]
[ 107-87-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 7.8% 2: 77.3%	With hydrogen In diethylene glycol dimethyl ether; water at 30℃; for 5h;
	With nickel kieselguhr at 100℃; Hydrogenation;
	With nickel kieselguhr at 100 - 160℃; Hydrogenation_.Hydrieren des Reaktionsprodukts an Kupferchromit; (+-)-pentanol-(2);

Reference： [1]Fujitsu, Hiroshi; Matsumura, Eiichi; Takeshita, Kenjiro; Mochida, Isao [Journal of the Chemical Society. Perkin transactions I, 1981, p. 2650 - 2655]
[2]Morgan; Hardy [Chemistry and industry, 1933, p. 519][Chemisches Zentralblatt, 1935, vol. 106, # I, p. 2001]
[3]Morgan; Hardy [Chemistry and industry, 1933, p. 519][Chemisches Zentralblatt, 1935, vol. 106, # I, p. 2001]

2
[ 75-07-0 ]
[ 67-64-1 ]
[ 625-33-2 ]

Yield	Reaction Conditions	Operation in experiment
9.6%	With sodium hydroxide In diethyl ether at 0℃; for 5h;
	With sodium hydroxide; diethyl ether und Destillation des Reaktionsprodukts mit wasserfreier Oxalsaeure;
	With caesium carbonate In methanol at 20℃; for 5.5h;

	With sodium hydroxide In water at 40℃;
	With sodium hydroxide In water at 25℃; for 6h;

Reference： [1]Munk, Vivienne P.; Cham, S. Tsuey; Fenton, Ronald R.; Hocking, Rosalie K.; Hambley, Trevor W. [Australian Journal of Chemistry, 2002, vol. 55, # 8, p. 523 - 529]
[2]Grignard; Fluchaire [Annales de Chimie (Cachan, France), 1928, vol. <10>9, p. 9]
[3]Kalmode, Hanuman P.; Vadagaonkar, Kamlesh S.; Murugan, Kaliyappan; Chaskar, Atul C. [New Journal of Chemistry, 2015, vol. 39, # 6, p. 4631 - 4639]
[4]He, Yan-Hong; He, Tao; Guo, Jun-Tao; Li, Rui; Xiang, Yang; Yang, Da-Cheng; Guan, Zhi [Catalysis science and technology, 2016, vol. 6, # 7, p. 2239 - 2248]
[5]Yu, Chang-Bin; Song, Bo; Chen, Mu-Wang; Shen, Hong-Qiang; Zhou, Yong-Gui [Organic Letters, 2019, vol. 21, # 23, p. 9401 - 9404]

3
[ 625-33-2 ]
[ 693-05-0 ]
[ 52221-45-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1974,vol. 10,p. 710 - 715
Zhurnal Organicheskoi Khimii,1974,vol. 10,p. 706 - 712

4
[ 95-20-5 ]
[ 625-33-2 ]
[ 18992-71-7 ]

Yield	Reaction Conditions	Operation in experiment
35%	In acetic acid for 48h; Heating;

Reference： [1]Bergman; Pelcman [Tetrahedron, 1988, vol. 44, # 16, p. 5215 - 5228]

5
[ 625-33-2 ]
[ 52784-32-4 ]
[ 87307-71-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With DBN In acetonitrile at 20 - 25℃; for 40h;

Reference： [1]Dauben, William G.; Bunce, Richard A. [Journal of Organic Chemistry, 1983, vol. 48, # 24, p. 4642 - 4648]

6
[ 625-33-2 ]
[ 104115-48-2 ]
C₂₈H₃₉NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With lithium diisopropyl amide In tetrahydrofuran at 0℃;

Reference： [1]Heathcock, Clayton H.; Davidsen, Steven K.; Mills, Sander; Sanner, Mark A. [Journal of the American Chemical Society, 1986, vol. 108, # 18, p. 5650 - 5651]

7
[ 625-33-2 ]
[ 138286-51-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	With Rose Bengal lactone In methanol; dichloromethane for 20h; Irradiation;

Reference： [1]Snider, Barry B.; Shi, Zhongping [Journal of the American Chemical Society, 1992, vol. 114, # 5, p. 1790 - 1800]

8
[ 625-33-2 ]
[ 107-87-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With limonene. for 0.25h; Heating;
94.2%	With potassium bis(trimethylsilyl)amide In tetrahydrofuran at 0℃; for 6h;
71%	With hydrogen In hexane for 3h; Ambient temperature; pH=7.6;

	With hydrogen In ethanol at 35℃; for 1h; Autoclave; chemoselective reaction;
	With 1-(ferrocenylmethylene)-3-butylimidazolium bromide; potassium hydroxide In isopropyl alcohol at 82℃; for 12h; chemoselective reaction;
97 %Chromat.	With methanol; C₂₅H₂₉ClNO₂Rh; potassium carbonate at 90℃; for 1h; chemoselective reaction;	2.2. Transfer hydrogenation of unsaturated ketones in methanol A Radley tube was charged with an unsaturated ketone (0.3mmol), catalyst (0.003 mmol) and K2CO3 (0.25 eq), to which was introduced MeOH (1.5 mL). The reaction mixture was heated to reflux at 90 °C for 1 h. The resulting mixture was then cooled to room temperature, followed by solvent evaporation under vacuum. The product was purified by flash column chromatography (hexane/ethyl acetate, 4:1).
55 %Chromat.	With 1,3-bis(4-fluorophenyl)imidazolium tetrafluoroborate; isopropyl alcohol; potassium hydroxide at 82℃; for 12h; Green chemistry;	A typical procedure for the transfer hydrogenation reaction is described General procedure: 1,3-diarylimidazolium salt 1 (0.0105 mmol, 3.6 mg) and KOH (0.112 g, 10 ml, 0.2 M in i-PrOH) were added to a round-bottom flask followed by the addition of cyclohexanone (2.1 mmol, 0.21 mL). The mixture was refluxed at 82 C for 12 h. The reaction progress was monitored by taking aliquots at time intervals which were passed through a pad of silica and injected into a GC. The identities of the products were assessed by comparison of their retention times with commercially available (Aldrich Chemical Co.) samples. The percentage conversions were obtained from integration values of the GC peaks which were related to residual unreacted ketones.
	With D-Glucose; NADPH In dimethyl sulfoxide at 30℃; for 1h; Enzymatic reaction;

Reference： [1]Holleben, Maria Luiza A. von; Zucolotto, Monica; Zini, Claudia A.; Oliveira, Eduardo R. [Tetrahedron, 1994, vol. 50, # 4, p. 973 - 978]
[2]Kim, Kwan Eung; Park, Soo Bong; Yoon, Nung Min [Synthetic Communications, 1988, vol. 18, # 1, p. 89 - 96]
[3]Januszkiewicz, Krzysztof R.; Alper, Howard [Canadian Journal of Chemistry, 1984, vol. 62, p. 1031 - 1033]
[4]Location in patent: experimental part Khan, Farooq-Ahmad; Vallat, Armelle; Süss-Fink, Georg [Journal of Molecular Catalysis A: Chemical, 2012, vol. 355, p. 168 - 173]
[5]Ikhile, Monisola I.; Bala, Muhammad D.; Nyamori, Vincent O.; Ngila, J. Catherine [Applied Organometallic Chemistry, 2013, vol. 27, # 2, p. 98 - 108]
[6]Aboo, Ahmed H.; Begum, Robina; Zhao, Liangliang; Farooqi, Zahoor H.; Xiao, Jianliang [Cuihua Xuebao/Chinese Journal of Catalysis, 2019, vol. 40, # 11, p. 1795 - 1799]
[7]Ikhile, Monisola Itohan; Nyamori, Vincent Onserio; Bala, Muhammad Dabai [Tetrahedron Letters, 2012, vol. 53, # 37, p. 4925 - 4928,4]
[8]Jongkind, Ewald P. J.; Fossey-Jouenne, Aurélie; Mayol, Ombeline; Zaparucha, Anne; Vergne-Vaxelaire, Carine; Paul, Caroline E. [ChemCatChem, 2022, vol. 14, # 2]

9
[ 625-33-2 ]
[ 108-98-5 ]
[ 174510-05-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydrogencarbonate In water at 20℃;
64%	With [Ni(2,6-bis[[(S)-2-(methyloxycarbonyl)-1-pyrrolidinyl]methyl]-pyridine)(CH₃CN)](ClO₄)2*H₂O In acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique;
12%	With C₃₉H₄₇N₇Ni₂O₅⁽³⁺⁾*3ClO₄^(1-) In acetonitrile at 20℃; for 2h;

	With piperidine In benzene
	With triethylamine
	With iron(III) chloride In dichloromethane at 20℃;

Reference： [1]Anselmi, Silvia; Liu, Siyu; Kim, Seong-Heun; Barry, Sarah M.; Moody, Thomas S.; Castagnolo, Daniele [Organic and Biomolecular Chemistry, 2021, vol. 19, # 1, p. 156 - 161]
[2]Lee, Way-Zen; Chiang, Chien-Wei; Kulkarni, Girish M.; Kuo, Ting-Shen [Journal of the Chinese Chemical Society, 2013, vol. 60, # 3, p. 245 - 250]
[3]Location in patent: scheme or table Lee, Way-Zen; Tseng, Huan-Sheng; Wang, Tzu-Li; Tsai, Hui-Lien; Kuo, Ting-Shen [Organometallics, 2010, vol. 29, # 13, p. 2874 - 2881]
[4]Tilak,B.D. et al. [Tetrahedron, 1966, vol. 22, p. 7 - 23]
[5]Cherkauskas, John P.; Cohen, Theodore [Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 6 - 8]
[6]Mao, Hui; You, Bing-Xin; Zhou, Lie-Jin; Xie, Ting-Ting; Wen, Yi-Hang; Lv, Xin; Wang, Xiao-Xia [Organic and Biomolecular Chemistry, 2017, vol. 15, # 29, p. 6157 - 6166]

10
[ 625-33-2 ]
[ 3465-72-3 ]
[ 117082-12-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 15h;

Reference： [1]Ienaga, Kazuharu; Yamamoto, Atsushi; Yamada, Toshio; Joh, Yoshinori [Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1037 - 1038]

11
[ 625-33-2 ]
[ 7565-59-5 ]
[ 65995-71-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With chloro-trimethyl-silane; boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -30℃;

Reference： [1]Hanson; Rieke [Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10775 - 10776]

12
[ 625-33-2 ]
cyclopentylzinc bromide [ No CAS ]
[ 27607-99-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With chloro-trimethyl-silane; boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -30℃;

Reference： [1]Hanson; Rieke [Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10775 - 10776]

13
[ 625-33-2 ]
[ 64-17-5 ]
[ 142-04-1 ]
[ 7705-08-0 ]
ZnCl₂ [ No CAS ]
[ 1198-37-4 ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 86,88

14
[ 1126-46-1 ]
[ 625-33-2 ]
[ 50793-51-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: Methyl 4-chlorobenzoate With tetrabutylammonium tetrafluoroborate; zinc(II) chloride In pyridine; acetonitrile Electrochemical reaction; Stage #2: 3-penten-2-one In pyridine; acetonitrile at 50℃; for 15h;

Reference： [1]Gomes, Paulo; Gosmini, Corinne; Périchon, Jacques [Synlett, 2002, # 10, p. 1673 - 1676]

15
[ 625-33-2 ]
[ 84109-76-2 ]
tert-butyl 2-oxo-1-(1-methyl-3-oxobutyl)cyclopentanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran at -20℃; for 24h;

Reference： [1]Hamashima, Yoshitaka; Hotta, Daido; Sodeoka, Mikiko [Journal of the American Chemical Society, 2002, vol. 124, # 38, p. 11240 - 11241]

16
[ 1569-50-2 ]
[ 625-33-2 ]
[ 95782-14-2 ]
(-)-(R)-pent-2-en-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With whole lyophilised cells of Rhodococcus ruber DSM; acetone In phosphate buffer at 30℃; for 38h;
12 %Chromat.	With Arabidopsis thaliana berberine bridge enzyme-like protein 15 L₁₈₂V; oxygen In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction; Optical yield = 20 %ee; enantioselective reaction;	2.4. Substrate screening General procedure: Reactions were carried out in 50 mM MES buffer pH 7.0 in the presence of 20% (v/v) DMSO. A total volume of 2 mL reaction mixture was incubated in 11 mL glass test tube with screw cap (Pyrex,Darmstadt, Germany) at 30 C in an orbital shaker at 110 rpm. The reaction was started by the addition of 10 L enzyme to achieve a final enzyme concentration of 1.2 M. After 24 h the reaction mixture was extracted with ethyl acetate (2 1 mL), the combined organic phase was dried with Na2SO4 and subjected to GC analysis to identify putative products.

Reference： [1]Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang [Tetrahedron Asymmetry, 2003, vol. 14, # 2, p. 275 - 280]
[2]Pils, Sabine; Schnabl, Kordula; Wallner, Silvia; Daniel, Bastian; Macheroux, Peter; Kljajic, Marko; Kupresanin, Nina; Breinbauer, Rolf; Fuchs, Michael; Rocha, Raquel; Schrittwieser, Joerg H.; Kroutil, Wolfgang [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 133, p. S6 - S14]

17
[ 1569-50-2 ]
[ 625-33-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Cu₂(phenanthroline)₂(μ-Cl)₂Cl₂; oxygen In acetonitrile at 20℃; for 5h;
21%	With (1R,2R)-1,2-di(naphthalen-1-yl)ethane-1,2-diamine; tert.-butylhydroperoxide; potassium carbonate In water at 95℃; for 16h;
	With oxygen In various solvent(s) at 82.84℃; for 6h;

	With oxygen In 4-methyl-1,2,3-trifluorobenzene at 20 - 83℃; for 6h;	18 Example 18 The same procedures as in Example 17 were repeated except that 3-penten-2-ol was used as a substrate in place of cyclohexanol, and the reaction time was changed to be 6 hours. The conversion of 3-penten-2-ol was 84%, and the selectivity to 3-penten-2-one was more than 99%.
	With silica gel; palladium at 90℃; for 24h; chemoselective reaction;
	With oxygen In toluene at 90℃; for 24h;
	With oxygen In toluene; 1,3,5-trimethyl-benzene at 90℃; for 1h;	2.4 Allylic alcohol selox Catalyst screening was performed using a Radleys Starfish carousel batch reactor on a 10cm3 scale at 90°C under a bubbled O2 flow (3cm3min-1 at 1bar). Catalyst (50mg) was added to a reaction mixture of allylic alcohol (8.4mmol, Sigma-Aldrich purity of all >95%), mesitylene (0.1cm3, Sigma-Aldrich 99%) as an internal standard, and toluene (10cm3, Fisher Scientific 99.8%). Control reactions in the absence of any solid phase, or presence of bare alumina supports, were conducted in parallel with tests on Pd/meso-Al2O3 and gave negligible conversion of any alcohols. Reactions were periodically sampled, with aliquot (0.25cm3) withdrawn, filtered, and diluted with toluene (1.75cm3, Fisher Scientific 99.8%) for triplicate analysed on a Varian 3900GC with CP-8400 autosampler (CP-Sil5 CB column, 15m x 0.25mm x 0.25 μm). Initial rates were calculated from the initial linear region of the alcohol conversion profiles (typically 0.3-1h reaction), with selectivity and overall mass balances calculated using calibrated response factors for reactants and products. Conversion and selectivity values are reported within ±3 % error, with mass balances in all cases ≥95 % during the first hour and ≥90 % over 24h. Catalyst recyclability was assessed by screening a spent quantity of catalysts from a scaled-up (by a factor of 2.5) to ensure significant catalyst recovery by hot filtration. Spent catalysts were stirred in 50ml toluene at 90°C for 10min (three times) before drying at 120°C for 2h and subsequent catalytic testing under identical conditions to those stated above.

Reference： [1]Location in patent: experimental part Hossain, Md. Munkir; Shyu, Shin-Guang [Advanced Synthesis and Catalysis, 2010, vol. 352, # 17, p. 3061 - 3068]
[2]Al-Hunaiti, Afnan; Räisänen, Minna; Pihko, Petri; Leskelä, Markku; Repo, Timo [European Journal of Organic Chemistry, 2014, vol. 2014, # 28, p. 6141 - 6144]
[3]Yamaguchi, Kazuya; Mizuno, Noritaka [Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4353 - 4361]
[4]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US2004/204597, 2004, A1 Location in patent: Page 5
[5]Location in patent: scheme or table Lee, Adam F.; Ellis, Christine V.; Naughton, James N.; Newton, Mark A.; Parlett, Christopher M. A.; Wilson, Karen [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 5724 - 5727]
[6]Parlett, Christopher M. A.; Bruce, Duncan W.; Hondow, Nicole S.; Newton, Mark A.; Lee, Adam F.; Wilson, Karen [ChemCatChem, 2013, vol. 5, # 4, p. 939 - 950]
[7]Parlett, Christopher M.A.; Durndell, Lee J.; Wilson, Karen; Bruce, Duncan W.; Hondow, Nicole S.; Lee, Adam F. [Catalysis Communications, 2014, vol. 44, p. 40 - 45]

18
[ 603-76-9 ]
[ 625-33-2 ]
[ 206050-43-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With silver hexafluoroantimonate; tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 20℃; for 8h;
37%	With acetic anhydride; acetic acid at 20 - 90℃; for 0.583333h;

Reference： [1]Li, Shuai-Shuai; Lin, Hui; Zhang, Xiao-Mei; Dong, Lin [Organic and Biomolecular Chemistry, 2015, vol. 13, # 4, p. 1254 - 1263]
[2]Kong, Aidi; Han, Xiuling; Lu, Xiyan [Organic Letters, 2006, vol. 8, # 7, p. 1339 - 1342]

19
[ 625-33-2 ]
[ 28588-74-1 ]
4-(2-methyl-furan-3-yl-thio)-pentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	In ethanol at 20℃; for 60h;	9 According to US Patent No. 5,145,703, 5 g of 2-methyl-3-furanthiol (43.85 mmol) and 7.5 g of 3-penten-2-one (89.28 mmol) were dissolved in 50 ml of ethanol. The solution was stirred for 60 hours at room temperature. The solvent was then distilled off in vacuum at 500C. The residue, 10.38 g, was purified by column chromatography (SiC>2, toluene/ethyl acetate 8:2) and afforded 4.41 g (18%) of a yellow oil (46.70%).13C NMR 206.45 (s); 156.35 (s); 140.57 (d); 116.02 (d); 108.33 (s); 50.49 (0;38.82 (d); 30.42 (q); 21.06 (q); 11.88 (q).1H NMR 7.29 (d, J = 1.54, IH); 6.33 (J, J= 2.05, IH); 3.39-3.28 (m, IH); 2.74-2.65(m, IH); 2.54-2.45 (m, IH); 2.34 (s, 3H); 2.13 (s, 3H); 1.23 (t, J = 6.66,3H).MS M+ = 198 (36); m/e : 114 (100); 85 (22); 71 (13); 69 (62); 59 (6); 53 (10);51 (10); 45 (11); 43 (78); 41 (31); 39 (19).

Reference： [1]Current Patent Assignee: Firmenich International SA - WO2008/15638, 2008, A2 Location in patent: Page/Page column 17

20
[ 625-33-2 ]
[ 2562-37-0 ]
4-methyl-5-(1-nitrocyclohex-2-enyl)pentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium azide; <i>L</i>-proline In dimethyl sulfoxide at 20℃; for 6h;

Reference： [1]Sun, Xiaohua; Sengupta, Sujata; Petersen; Wang, Hong; Lewis, James P.; Shi, Xiaodong [Organic Letters, 2007, vol. 9, # 22, p. 4495 - 4498]

21
[ 625-33-2 ]
[ 6065-11-8 ]
C₁₃H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium azide; <i>L</i>-proline In dimethyl sulfoxide at 20℃; for 4h;

Reference： [1]Sun, Xiaohua; Sengupta, Sujata; Petersen; Wang, Hong; Lewis, James P.; Shi, Xiaodong [Organic Letters, 2007, vol. 9, # 22, p. 4495 - 4498]

22
[ 625-33-2 ]
[ 142458-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CH₃ONa / methanol 2: 81 percent / toluene / Heating
	Multi-step reaction with 2 steps 1: 1.) sodium methanolate / 1.) 0 deg C, 30 min, 2.) a) 0 deg C, 1 h, b) reflux, 2 h 2: 22 percent / toluene / 6 h / Heating

Reference： [1]Edafiogho; Moore; Farrar; Nicholson; Scott [Journal of Pharmaceutical Sciences, 1994, vol. 83, # 1, p. 79 - 84]
[2]Edafiogho; Hinko; Chang; Moore; Mulzac; Nicholson; Scott [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2798 - 2805]

23
[ 625-33-2 ]
[ 41085-27-2 ]

Reference： [1]Journal of Organic Chemistry,1963,vol. 28,p. 928 - 932

24
[ 625-33-2 ]
[ 42738-68-1 ]
C₁₄H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water In ethanol at 20℃; for 168h;	5 Synthesis of (8S,8aS)-8a-allyl-3,4,8,8a-tetrahydro-8-methylnaphthalen- 1 ,6(2H,7H)-dione; To a solution of 13.4 g (88.1 mmol) 2-allylcyclohexane-1 ,3-dione in 75 ml of water 8.2 g (97.2 mmol) of pent-3-ene-2-one is added. 1.5 ml of ethanol is added to enhance the solubility and the developing suspension is stirred for 7 days at room temperature (after 6 days the white solid is completely dissolved). The solution is mixed with 200 ml of toluene and the aqueous phase is extracted three times each with 200 ml of dichloromethane. The combined organic phases are washed with saturated NaCI solution and dried over MgSO4. The solvent is removed under reduced pressure and the crude product is purified via column chromatography.Afterwards it is admixed with 400 ml of DMF, 24.8 g (150 mmol) L-phenylalanine and 18.1 g (111 mmol) D-camphorsulfonic acid are added. The solution is stirred over night at room temperature and afterwards the temperature is increased every24 h in each case by 100C until the final value of 7O0C. The solution is cooled toO0C and mixed with 400 ml of a saturated NaHCO3 solution. After 30 min of stirring it is extracted each time with 300 ml of diethylether. The combined organic phases are washed with saturated NaCI solution and dried over MgSO4.The solvent is removed under reduced pressure and the crude product is purified via column chromatography (white solid).Mp.: 520CYield: 10.4 g, 47.7 mmol, 54 % Rf-value: 0.37 (cyclohexane/ethylacetate 3:1 v/v)[ccf° = +54° (c = 1.00, CHCI3)1H-NMR (400 MHz, CDCI3): δ 0.84 (d, J = 7.6 Hz1 3H), 1.54-1.70 (m, 1 H), 1.91-2.74 (m, 11 H), 5.01-5.13 (m, 2H), 5.58-5.71 (m, 1 H).13C-NMR (100.6 MHz, CDCI3): δ 17.0, 21.1 , 33.2, 33.7, 40.3, 41.2, 43.8, 58.6, 119.3, 125.3, 132.7, 163.8, 197.9, 210.2.GCMS, m/z (rel int. %): 218 (52) [M+], 203 (31 ), 190 (10), 175 (24), 161 (22), 149(100), 135 (26), 119 (14), 105 (41 ), 91 (49), 77 (36), 55 (27), 41 (23).HRMS (FAB): calc. for C14H18O2: 218.1307, found: 219.1391 [M+H]+.

Reference： [1]Current Patent Assignee: TECHNICAL UNIVERSITY OF DORTMUND; MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFT E.V.; UNIVERSITY OF BERN - WO2006/69787, 2006, A1 Location in patent: Page/Page column 68

25
[ 625-33-2 ]
[ 13170-43-9 ]
[ 934233-60-0 ]

Yield	Reaction Conditions	Operation in experiment
43%	With copper(I) bromide In diethyl ether at -5 - 20℃; for 1h;	1 Preparation of 4-methyl-5-(trimethylsilyl)pentan-2-one Preparation of 4-methyl-5-(trimethylsilyl)pentan-2-one A solution of 8,00 g pent-3-en-2-one in 50 mL dry diethyl ether was dropped to a solution of 73.5 mL of chloro[(trimethylsilyl)methyl]magnesium (1.0M in diethyl ether) and 955 mg of CuBr at -5°C under Argon. The mixture was stirred for 1 hour at room temperature. An aqueous work-up followed by silica gel chromatography yielded 5,20 g (43%) of a colourless oil. [M+1]=173.

Reference： [1]Current Patent Assignee: BAYER AG - EP1772449, 2007, A1 Location in patent: Page/Page column 30-31

26
[ 120-72-9 ]
[ 625-33-2 ]
[ 59715-09-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With aluminium(III) triflate at 80℃; for 0.133333h; Microwave irradiation; regioselective reaction;
91%	With N-[(perfluorobutyl)sulfonyl]-3-{N-[(perfluorobutyl)sulfonyl]sulfamoyl}benzamide In water at 30℃; for 3h;
90%	With ionic liquid immobilized on silica-SO₂Cl In diethyl ether at 20℃; for 5h;

78%	With sodium ligninsulfonate-immobilized Sc(OTf)₃ In ethanol
77%	With zirconium(IV) chloride In dichloromethane at 20℃;
76%	With silver hexafluoroantimonate; tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 20℃; for 12h;
72%	With graphite oxide In tetrahydrofuran; water at 20℃; for 6.5h;	General procedure. General procedure: Typical procedure for the Friedel-Crafts reaction of indoles to α,β-unsaturated ketones: To a stirred mixture of indole (117 mg, 1mmol), and methyl vinyl ketone (85 mg, 1.2 mmol) in H2O/THF (7:3, 2 mL ) solution, GO (20 mg) was added. The reaction mixture was allowed to stir at room temparature and progress of the reaction was monitored by TLC. After complete consumption of indole, water (5 mL) was added and the aqueous layer was extracted with ethyl acetate (2 X 5 mL). The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was passed through a short pad of silica gel (petroleum ether/ethyl acetate) to afford the analytically pure product in 94% yield.The aqueous layer containing the catalyst was filtered and washed with acetone,water and dried in a dessicator and used for the next cyle.
70%	With dichloro bis(acetonitrile) palladium(II) In 1,2-dichloro-ethane at 30℃; for 6h; regioselective reaction;	Representative Procedure for the Michael Addition of Indoles with Enones General procedure: A mixture of but-3-en-2-one 4b (42 mg, 0.6 mmol), 1H-indole 1a (58.5 mg, 0.5 mmol), PdCl2(MeCN)2 (6.5 mg, 0.025 mmol) in 2 mL of DCE was stirred at at room temperature (30 oC) for appropriate time. Then, solvent was removed under reduced pressure, and the mixture was subjected to column chromatography over silica gel (100-200 mesh, eluent: petroleum ether 60-80 oC/ethylacetate 4:1 v/v) to afford a corresponding product 5d as a white solid in 89% (83 mg) isolated yield.

Reference： [1]Gohain, Mukut; Jacobs; Marais, Charlene; Bezuidenhoudt, Barend C. B. [Australian Journal of Chemistry, 2013, vol. 66, # 12, p. 1594 - 1599]
[2]Cheng, Yuan; Ou, Xiongyu; Ma, Jimei; Sun, Linhao; Ma, Zhong-Hua [European Journal of Organic Chemistry, 2019, vol. 2019, # 1, p. 66 - 72]
[3]Hagiwara, Hisahiro; Sekifuji, Masayoshi; Hoshi, Takashi; Suzuki, Toshio; Quanxi, Bao; Qiao, Kun; Yokoyama, Chiaki [Synlett, 2008, # 4, p. 608 - 610]
[4]Sun, Shaohuan; Bai, Rongxian; Gu, Yanlong [Chemistry - A European Journal, 2014, vol. 20, # 2, p. 549 - 558]
[5]Portela-Cubillo, Fernando; Surgenor, Brian A.; Aitken, R. Alan; Walton, John C. [Journal of Organic Chemistry, 2008, vol. 73, # 20, p. 8124 - 8127]
[6]Li, Shuai-Shuai; Lin, Hui; Zhang, Xiao-Mei; Dong, Lin [Organic and Biomolecular Chemistry, 2015, vol. 13, # 4, p. 1254 - 1263]
[7]Vijay Kumar; Rama Rao [Tetrahedron Letters, 2011, vol. 52, # 40, p. 5188 - 5191]
[8]Mohapatra, Swapna Sarita; Mukhi, Priyabrata; Mohanty, Anuradha; Pal, Satyanarayan; Sahoo, Aditya Omprakash; Das, Debjit; Roy, Sujit [Tetrahedron Letters, 2015, vol. 56, # 42, p. 5709 - 5713]

27
[ 10075-50-0 ]
[ 625-33-2 ]
[ 1018636-36-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-[(perfluorobutyl)sulfonyl]-3-{N-[(perfluorobutyl)sulfonyl]sulfamoyl}benzamide In water at 30℃; for 5h;
72%	With zirconium(IV) chloride In dichloromethane at 20℃;

Reference： [1]Cheng, Yuan; Ou, Xiongyu; Ma, Jimei; Sun, Linhao; Ma, Zhong-Hua [European Journal of Organic Chemistry, 2019, vol. 2019, # 1, p. 66 - 72]
[2]Portela-Cubillo, Fernando; Surgenor, Brian A.; Aitken, R. Alan; Walton, John C. [Journal of Organic Chemistry, 2008, vol. 73, # 20, p. 8124 - 8127]

28
[ 625-33-2 ]
[ 80-15-9 ]
[ 17257-79-3 ]
C₁₄H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 9-epi-9-amino-9-deoxyquinine; trifluoroacetic acid In toluene at 0℃; for 12h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Lu, Xiaojie; Liu, Yan; Sun, Bingfeng; Cindric, Brittany; Deng, Li [Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8134 - 8135]

29
[ 625-33-2 ]
[ 1041437-34-6 ]
[ 1041437-32-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium In dichloromethane at 20℃; for 2h; Inert atmosphere;
63%	With Hoveyda-Grubbs catalyst second generation In dichloromethane for 2h; Inert atmosphere;

Reference： [1]Yang, Hua; Carter, Rich G.; Zakharov, Lev N. [Journal of the American Chemical Society, 2008, vol. 130, # 29, p. 9238 - 9239]
[2]Yang, Hua; Carter, Rich G. [Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 4929 - 4938]

30
[ 625-33-2 ]
[ 608101-55-9 ]
[ 1025362-97-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-(2,2-diphenylvinylidene)-2,2-diphenylcyclopropane With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 3-penten-2-one In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;

Reference： [1]Lu, Jian-Mei; Shi, Min [Organic Letters, 2008, vol. 10, # 10, p. 1943 - 1946]

31
[ 625-33-2 ]
[ 64420-86-6 ]
[ 1096017-08-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 3-penten-2-one With 1.5C₁₃H₁₇NO₄*C₂₀H₂₇N₃O In chloroform at 23℃; for 0.166667h; Stage #2: O-p-toluenesulfonyl benzyloxyhydroxamate With sodium hydrogencarbonate In chloroform at 23℃; for 16h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Pesciaioli, Fabio; De Vincentiis, Francesco; Galzerano, Patrizia; Bencivenni, Giorgio; Bartoli, Giuseppe; Mazzanti, Andrea; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2008, vol. 47, # 45, p. 8703 - 8706]

32
[ 625-33-2 ]
[ 108-26-9 ]
[ 1158651-97-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 3-penten-2-one With 9-epi-9-amino-9-deoxyquinine; benzoic acid In toluene at 20℃; for 0.333333h; Stage #2: 3-methyl-2-pyrazoline-5-one In toluene at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Gogoi, Sanjib; Zhao, Cong-Gui; Ding, Derong [Organic Letters, 2009, vol. 11, # 11, p. 2249 - 2252]

33
[ 625-33-2 ]
[ 35087-28-6 ]
[ 1158652-06-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3-penten-2-one With 9-epi-9-amino-9-deoxyquinine; benzoic acid In toluene at 20℃; for 0.333333h; Stage #2: 5-ethyl-2,4-dihydro-3H-pyrazol-3-one In toluene at 20℃; for 26h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Gogoi, Sanjib; Zhao, Cong-Gui; Ding, Derong [Organic Letters, 2009, vol. 11, # 11, p. 2249 - 2252]

34
[ 625-33-2 ]
[ 98-80-6 ]
[ 32587-80-7 ]
[ 67110-72-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorobis(ethylene)rhodium(I) dimer; ethyl 2,3-dideoxy-4-O-diphenylphosphino-6-O-trityl-α-D-erythro-hex-2-enopyranoside; potassium hydroxide In 1,4-dioxane; water at 50℃; for 5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
	With (S,Rp)-[1-(2-bromoferrocenyl)ethyl]diphenylphosphine; potassium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In toluene at 20℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
	With chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine; potassium hydroxide In water; toluene at 20 - 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

	With chlorobis(ethylene)rhodium(I) dimer; ethyl 2,3-dideoxy-4-O-diphenylphosphino-6-O-trityl-α-D-erythro-hex-2-enopyranoside; potassium hydroxide In 1,4-dioxane; water at 30℃; for 16h; Inert atmosphere; optical yield given as %ee;
	With chlorobis(ethylene)rhodium(I) dimer; (3R,4R)-4-N-phthalimido-1,5-hexadiene-3-ol; potassium hydroxide In 1,4-dioxane; water at 20℃; for 6h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
	With Rh(acac)((S)-Ph₂PNC₄H₄MeCH₂Ph); potassium hydroxide In 1,4-dioxane; water at 30℃; for 10h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	4.4.1. General procedure for the rhodium-catalyzed asymmetric 1,4-addition (Table 2 and Table 3) General procedure: At first, KOH (50 μL, 0.10-0.20 mmol; 2.0-4.0 M aqueous) was added to a solution of [RhCl(ligand)]2 (10 μmol Rh), α,β-unsaturated ketone (0.20 mmol), and arylboronic acid (0.22-0.30 mmol) in dioxane (0.50 mL), and the resulting mixture was stirred for 10 h at 30 °C. This was directly passed through a pad of silica gel with EtOAc and the solvent was removed under vacuum. The residue was purified by silica gel preparative TLC with EtOAc/hexane to afford the 1,4-adduct.
	With C₂₉H₃₁NO₂PRh; potassium hydroxide In 1,4-dioxane; water at 30℃; for 10h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	4.4.1. General procedure for the rhodium-catalyzed asymmetric 1,4-addition (Table 2 and Table 3) General procedure: At first, KOH (50 μL, 0.10-0.20 mmol; 2.0-4.0 M aqueous) was added to a solution of [RhCl(ligand)]2 (10 μmol Rh), α,β-unsaturated ketone (0.20 mmol), and arylboronic acid (0.22-0.30 mmol) in dioxane (0.50 mL), and the resulting mixture was stirred for 10 h at 30 °C. This was directly passed through a pad of silica gel with EtOAc and the solvent was removed under vacuum. The residue was purified by silica gel preparative TLC with EtOAc/hexane to afford the 1,4-adduct.
56 % ee	With chlorobis(ethylene)rhodium(I) dimer; (-)-6-benzyl-3-((tert-butyldimethylsilyl)oxy)-8-(diphenylphosphino)-8-azabicyclo[3.2.1]oct-6-ene-P-borane; potassium hydroxide In 1,4-dioxane; water at 50℃; for 3h; Inert atmosphere; Schlenk technique; Overall yield = 69 %; enantioselective reaction;
81 % ee	With chlorobis(ethylene)rhodium(I) dimer; (+)-3-((tert-butyldimethylsilyl)oxy)-8-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxa-phosphepin-4-yl)-8-azabicyclo[3.2.1]oct-6-ene; potassium hydroxide In 1,4-dioxane; water at 22℃; for 3h; Inert atmosphere; Schlenk technique; Overall yield = 85 %; enantioselective reaction;
57 % ee	With chlorobis(ethylene)rhodium(I) dimer; (R)-(-)-[η⁶-1-diphenylphosphino-2-(3-diphenylphosphino-2-methylpropenyl)benzene-P]chromium(0) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 24h; Inert atmosphere; Schlenk technique; Overall yield = 31 %; enantioselective reaction;
88 % ee	With chlorobis(ethylene)rhodium(I) dimer; (S)-(+)-[η⁶-1-bis(3,5-dimethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)benzene-P]chromium(0) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 24h; Inert atmosphere; Schlenk technique; Overall yield = 34 %; enantioselective reaction;
	With potassium hydroxide In 1,4-dioxane; water at 50℃; for 8h;
32 % ee	With chlorobis(ethylene)rhodium(I) dimer; [η⁵-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 9h; Inert atmosphere; Overall yield = 43 %;

Reference： [1]Minuth, Tobias; Boysen, Mike M. K. [Organic Letters, 2009, vol. 11, # 18, p. 4212 - 4215]
[2]Location in patent: experimental part Suzuma, Yoshinori; Hayashi, Shoko; Yamamoto, Tetsuya; Oe, Yohei; Ohta, Tetsuo; Ito, Yoshihiko [Tetrahedron Asymmetry, 2009, vol. 20, # 23, p. 2751 - 2758]
[3]Lang, Feng; Li, Dong; Chen, Junmin; Chen, Jun; Li, Liangchun; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian [Advanced Synthesis and Catalysis, 2010, vol. 352, # 5, p. 843 - 846]
[4]Location in patent: experimental part Grugel, Holger; Minuth, Tobias; Boysen, Mike M. K. [Synthesis, 2010, # 19, p. 3248 - 3258]
[5]Trost, Barry M.; Burns, Aaron C.; Tautz, Thomas [Organic Letters, 2011, vol. 13, # 17, p. 4566 - 4569]
[6]Location in patent: experimental part Narui, Rintaro; Hayashi, Sayuri; Otomo, Haruka; Shintani, Ryo; Hayashi, Tamio [Tetrahedron Asymmetry, 2012, vol. 23, # 3-4, p. 284 - 293]
[7]Location in patent: experimental part Narui, Rintaro; Hayashi, Sayuri; Otomo, Haruka; Shintani, Ryo; Hayashi, Tamio [Tetrahedron Asymmetry, 2012, vol. 23, # 3-4, p. 284 - 293]
[8]Vlahovic, Sandra; Schaedel, Nicole; Tussetschlaeger, Stefan; Laschat, Sabine [European Journal of Organic Chemistry, 2013, # 8, p. 1580 - 1590]
[9]Vlahovic, Sandra; Schaedel, Nicole; Tussetschlaeger, Stefan; Laschat, Sabine [European Journal of Organic Chemistry, 2013, # 8, p. 1580 - 1590]
[10]Ogasawara, Masamichi; Tseng, Ya-Yi; Arae, Sachie; Morita, Tomotaka; Nakaya, Takeshi; Wu, Wei-Yi; Takahashi, Tamotsu; Kamikawa, Ken [Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9377 - 9384]
[11]Ogasawara, Masamichi; Tseng, Ya-Yi; Arae, Sachie; Morita, Tomotaka; Nakaya, Takeshi; Wu, Wei-Yi; Takahashi, Tamotsu; Kamikawa, Ken [Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9377 - 9384]
[12]Dong, Jinqiao; Liu, Yan; Cui, Yong [Chemical Communications, 2014, vol. 50, # 95, p. 14949 - 14952]
[13]Kamikawa, Ken; Tsen, Ya-Yi; Jian, Jia-Hong; Takahashi, Tamotsu; Ogasawara, Masamichi [Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1545 - 1553]

35
[ 625-33-2 ]
[ 5188-07-8 ]
[ 143764-28-7 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In water; acetonitrile at 2 - 60℃;	8 To a three-neck 50 mL round bottom flask equipped with a temperature probe, magnetic stirring, and bleach scrubber was charged in sequence 1.46 g (24.31 mmol) of glacial acetic acid followed by 1.73 g (21.57 mmol) of 65% 3-penten-2-one (contains 30% mesityl oxide), followed by 4.0 mL of acetonitrile, and the mixture was then cooled in an ice-water bath. To this mixture was con-added 10 g (21.40 mmol) of a 15 wt % sodium thiomethoxide in water solution over a 23 min period. The internal reaction temperature rose from 2° C. to 4° C. during the sodium thiomethoxide addition. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and stirred for an additional 1 h. The reaction mixture was then heated at 50-60° C. for 30 min at which time GC peak area indicated a 3-pentene-2-one:mesityl oxide:4-(methylthio)pentan-2-one ratio of 4:16:80. After cooling to ambient temperature, the organic layer was separated and concentrated on a rotary evaporator to give 2.10 g of 4-(methylthio)pentan-2-one as a yellow oil (yield was 77% based on theoretical yield). 1H NMR (300 MHz, CDCl3) δ 1.3 (d, J=7 Hz, 3H), 2.1 (s, 3H), 2.2 (s, 3H), 2.6 (dd, J=17, 8 Hz, 1H), 2.8 (dd, J=17, 8 Hz, 1H), 3.2 (m, 1H). 13C NMR (75.5 MHz, CDCl3) δ 13.4, 20.9, 30.5, 36.2, 50.4, 206.7. GC/EIMS (relative peak intensity) m/z. 132 (100), 89 (93), 75 (99).

Reference： [1]Current Patent Assignee: CORTEVA INC - US2010/48939, 2010, A1 Location in patent: Page/Page column 4

36
[ 625-33-2 ]
[ 1215309-20-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 3-penten-2-one With lithium aluminium deuteride In diethyl ether at 0℃; Stage #2: With water; sodium hydroxide In diethyl ether at 0℃;

Reference： [1]Mukherjee, Paramita; Widenhoeferst, Ross A. [Organic Letters, 2010, vol. 12, # 6, p. 1184 - 1187]

37
[ 625-33-2 ]
[ 6945-92-2 ]
[ 1227832-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol; at 20℃;	Step A: Preparation of ethyl 4,5-dihydro-3,5-dimethyl-lH-pyrazole-l-acetate A mixture of ethyl hydrazinoacetate hydrochloride (1.55 g, 10 mmol), 3-pentene-2-one(0.95 mL, 10 mmol) and sodium bicarbonate (1.00 g, 11.9 mmol) in ethanol (10 mL) was stirred at room temperature overnight. The reaction mixture was then filtered and concentrated under reduced pressure. The resulting oil was purified by medium pressure liquid chromatography on silica gel (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a yellow oil (0.26 g).1H NMR (CDCl3): delta 1.27 (m, 6 H), 1.94 (s, 3H), 2.35 (m, IH), 2.75 (m, IH), 3.42 (m, IH),3.60-3.85 (m 2H), 4.20 (m, 2H).

Reference： [1]Patent: WO2010/65579,2010,A2 .Location in patent: Page/Page column 82

38
[ 625-33-2 ]
[ 1134192-86-1 ]
[ 1134192-87-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	In dichloromethane at 20℃; for 3.5h;	2 Example 2 Enone 5: To a solution of 31 (252 mg, 0.752 mmol) and 2-pentenone (94 mg, 1.11 mmol) in CH2Cl2 (3.7 mL) was added 2nd Gen. Hoveyda-Grubbs catalyst (23.3 mg, 37.3 μmol) at room temperature. After 3.5 hours, the reaction was loaded directly onto silica gel and was purified by chromatography, eluting with 10-30% EtOAc/hexanes, to give 5 (178 mg, 0.472 mmol, 63%) as colorless oil as well as recovered 31 (75 mg, 0.224 mmol, 30%): IR (neat) 2929, 2095, 1712, 1665, 1449, 1308, 1252, 1144, 1075 cm-1; 1H NMR (300 MHz, CDCl3) δ 7.73-7.81 (m, 3H), 7.60-7.68 (m, 2H), 6.78 (dt, J=16.0, 6.8 Hz, 1H), 6.13 (d, J=16.0 Hz, 1H), 4.16 (t, J=7.6 Hz, 1H), 3.27 (t, J=6.3 Hz, 2H), 2.99-3.07 (m, 1H), 2.53-2.68 (m, 1H), 2.16-2.31 (m, 5H), 1.95 (q, J=7.6 Hz, 2H), 1.64-1.86 (m, 2H), 1.47-1.54 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 201.4, 198.5, 146.6, 136.1, 134.6, 131.9, 129.4, 129.3, 74.5, 50.8, 44.3, 31.3, 27.1, 26.3, 24.6, 21.6; HRMS (FAB+) calcd. for C18H24N3O4S (M+H) 378.1488, found 378.1489.
63%	With Hoveyda-Grubbs catalyst second generation In dichloromethane at 20℃; for 3.5h; Inert atmosphere;

Reference： [1]Current Patent Assignee: OREGON HEALTH & SCIENCE UNIVERSITY - US2010/184986, 2010, A1 Location in patent: Page/Page column 44
[2]Yang, Hua; Carter, Rich G. [Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 4929 - 4938]

39
[ 625-33-2 ]
[ 62-53-3 ]
[ 1198-37-4 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 2336 - 2340

40
[ 923604-74-4 ]
[ 625-33-2 ]
[ 1235835-77-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; for 36h;
68%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; for 36h;

Reference： [1]Yang, Hua; Carter, Rich G. [Organic Letters, 2010, vol. 12, # 13, p. 3108 - 3111]
[2]Yang, Hua; Banerjee, Somdev; Carter, Rich G. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4851 - 4863]

41
[ 625-33-2 ]
[ 821-77-2 ]
[ 1235835-69-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 6h; Darkness;
43%	With Hoveyda-Grubbs catalyst second generation In dichloromethane at 20℃; for 6h; Darkness;

Reference： [1]Yang, Hua; Carter, Rich G. [Organic Letters, 2010, vol. 12, # 13, p. 3108 - 3111]
[2]Yang, Hua; Banerjee, Somdev; Carter, Rich G. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4851 - 4863]

42
[ 625-33-2 ]
[ 59137-50-7 ]
[ 1235835-68-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 24h;
89%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 24h;

Reference： [1]Yang, Hua; Carter, Rich G. [Organic Letters, 2010, vol. 12, # 13, p. 3108 - 3111]
[2]Yang, Hua; Banerjee, Somdev; Carter, Rich G. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4851 - 4863]

43
[ 625-33-2 ]
[ 41795-35-1 ]
[ 1235835-70-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 13h;
93%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 13h;

Reference： [1]Yang, Hua; Carter, Rich G. [Organic Letters, 2010, vol. 12, # 13, p. 3108 - 3111]
[2]Yang, Hua; Banerjee, Somdev; Carter, Rich G. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 25, p. 4851 - 4863]

44
[ 625-33-2 ]
[ 98-80-6 ]
[ 67110-72-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With BF₄^(1-)*C₆₈H₄₄N₂O₄P₂Rh⁽¹⁺⁾; water; potassium hydroxide In 1,4-dioxane at 60℃; for 1h; Anaerobic conditions; Combinatorial reaction / High throughput screening (HTS); optical yield given as %ee; enantioselective reaction;
78%	With chlorobis(ethylene)rhodium(I) dimer; (R<SUB>S</SUB>)-N-(cinnamyl)-2-methylpropane-2-sulfinamide; potassium hydroxide In methanol; water at 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
60%	With chlorobis(ethylene)rhodium(I) dimer; [η⁵-1-bis(3,5-di(trifluormethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 9h; Inert atmosphere; enantioselective reaction;

Reference： [1]Location in patent: experimental part Dorta, Romano; Drinkel, Emma; Briceno, Alexander; Dorta, Reto [Organometallics, 2010, vol. 29, # 11, p. 2503 - 2514]
[2]Khiar, Noureddine; Salvador, Alvaro; Chelouan, Ahmed; Alcudia, Ana; Fernandez, Inmaculada [Organic and Biomolecular Chemistry, 2012, vol. 10, # 12, p. 2366 - 2368]
[3]Kamikawa, Ken; Tsen, Ya-Yi; Jian, Jia-Hong; Takahashi, Tamotsu; Ogasawara, Masamichi [Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1545 - 1553]

45
[ 625-33-2 ]
[ 95-55-6 ]
[ 115310-98-0 ]

Yield	Reaction Conditions	Operation in experiment
		Synthetic Example 7; In a three-necked flask were placed 33 g of o-aminophenol and 207 g of concentrated hydrochloric acid and the mixture was heated to the reflux temperature and stirred for 1 hour. To the mixture being heated under reflux was slowly added 51 g of 3-penten-2-one with a purity of 65% over 2 hours and stirring was continued for another 2 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, 300 ml of a 48% aqueous solution of NaOH was added until the aqueous phase became alkaline. Ethyl acetate was added further, the organic layer was recovered and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by gas chromatography, recrystallized from hexane and the crystals collected by filtration were washed with hexane and dried at 80 C. under reduced pressure to give 18.9 g of 2,4-dimethyl-8-quinolinol.

Reference： [1]Patent: US2010/256377,2010,A1 .Location in patent: Page/Page column 18
[2]Journal of Fluorescence,2018,vol. 28,p. 1121 - 1126

46
[ 696-63-9 ]
[ 625-33-2 ]
[ 1233849-11-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1-methyl-imidazolium p-toluenesulfonic acid at 20℃; for 4h; neat (no solvent);
96%	With [Ni(2,6-bis[[(S)-2-(methyloxycarbonyl)-1-pyrrolidinyl]methyl]-pyridine)(CH₃CN)](ClO₄)2*H₂O In acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique;
41%	With C₃₉H₄₇N₇Ni₂O₅⁽³⁺⁾*3ClO₄^(1-) In acetonitrile at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Han, Feng; Yang, Lei; Li, Zhen; Xia, Chungu [Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 346 - 354]
[2]Lee, Way-Zen; Chiang, Chien-Wei; Kulkarni, Girish M.; Kuo, Ting-Shen [Journal of the Chinese Chemical Society, 2013, vol. 60, # 3, p. 245 - 250]
[3]Location in patent: scheme or table Lee, Way-Zen; Tseng, Huan-Sheng; Wang, Tzu-Li; Tsai, Hui-Lien; Kuo, Ting-Shen [Organometallics, 2010, vol. 29, # 13, p. 2874 - 2881]

47
[ 625-33-2 ]
[ 65304-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-penten-2-one With Oxone; sodium bromide In dichloromethane; water at 0 - 40℃; for 20.25h; Stage #2: With triethylamine In dichloromethane; water at 0℃; for 4.33333h;
	Multi-step reaction with 2 steps 1: bromine / 0.58 h / Cooling with ice 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / Cooling with ice
	With bromine; triethylamine In diethyl ether; chloroform at 0 - 20℃;

Stage #1: 3-penten-2-one With bromine In dichloromethane at 0℃; for 0.25h; Stage #2: With triethylamine In dichloromethane for 0.25h;

Reference： [1]Yagoubi, Myriam; Cruz, Ana C. F.; Nichols, Paula L.; Elliott, Richard L.; Willis, Michael C. [Angewandte Chemie - International Edition, 2010, vol. 49, # 43, p. 7958 - 7962]
[2]Current Patent Assignee: Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - JP2015/34179, 2015, A
[3]Poulsen, Pernille H.; Li, Yang; Lauridsen, Vibeke H.; Jørgensen, Danny K. B.; Palazzo, Teresa A.; Meazza, Marta; Jørgensen, Karl Anker [Angewandte Chemie - International Edition, 2018, vol. 57, # 33, p. 10661 - 10665][Angew. Chem., 2018, vol. 130, # 33, p. 10821 - 10825,5]
[4]Chao, Tzu-Hsuan; Cheng, Mu-Jeng; Kardile, Rahul Dadabhau; Liu, Rai-Shung [Angewandte Chemie - International Edition, 2020, vol. 59, # 26, p. 10396 - 10400][Angew. Chem., 2020, vol. 132, # 26, p. 10482 - 10486,5]

48
[ 625-33-2 ]
[ 942070-20-4 ]
[ 1258071-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; potassium hydroxide In tert-butyl methyl ether at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation;

Reference： [1]Tajuddin, Hazmi; Shukla, Lena; Maxwell, Aoife C.; Marder, Todd B.; Steel, Patrick G. [Organic Letters, 2010, vol. 12, # 24, p. 5700 - 5703]

49
[ 625-33-2 ]
[ 365564-07-4 ]
[ 1258071-64-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5700 - 5703

50
[ 625-33-2 ]
[ 325142-95-8 ]
[ 68118-13-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5700 - 5703

51
[ 95-14-7 ]
[ 625-33-2 ]
[ 1340332-19-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1-methyl-imidazolium p-toluenesulfonic acid In dichloromethane at 20℃; for 3h;

Reference： [1]Location in patent: experimental part Han, Feng; Yang, Lei; Li, Zhen; Xia, Chungu [Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 346 - 354]

52
[ 625-33-2 ]
[ 18039-42-4 ]
[ 1353002-70-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1-methyl-imidazolium p-toluenesulfonic acid In dichloromethane at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Han, Feng; Yang, Lei; Li, Zhen; Xia, Chungu [Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 346 - 354]

53
1-bromomethyl-2-vinyl-cyclohexane [ No CAS ]
[ 625-33-2 ]
C₁₁H₁₇BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With Hoveyda-Grubbs catalyst second generation In dichloromethane for 12h; Reflux; Inert atmosphere;	6.8.5. Cross-metathesis General procedure: A flame-dried round-bottom flask equipped with reflux condenser was charged with the bromide (1.21 g, 6 mmol), crotonaldehyde (0.49 mL, 6 mmol), and dichloromethane (30 mL). Hoveyda-Grubbs catalyst22 (188 mg, 0.3 mmol) was subsequently added as a solid, producing a light brown/green solution, which was refluxed for 12 h. The mixture was then plugged through a pad of silica gel and concentrated in vacuo. Yield after column chromatography (1.33 g, 56%).

Reference： [1]Location in patent: experimental part Cran, John W.; Krafft, Marie E.; Seibert, Kimberly A.; Haxell, Thomas F.N.; Wright, James A.; Hirosawa, Chitaru; Abboud, Khalil A. [Tetrahedron, 2011, vol. 67, # 51, p. 9922 - 9943]

54
[ 625-33-2 ]
[ 1119-51-3 ]
7-bromo-3-hepten-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Inert atmosphere; Reflux;	6.9. Synthesis of compounds 57, 58, 67 and 68: general procedure General procedure: A flame-dried round-bottom flask equipped with reflux condenser was charged with 5-bromo-1-pentene (1.04 g, 7 mmol), 3-penten-2-one (2.1 mL, 7 mmol), and dichloromethane (35 mL). Grubbs second generation catalyst22 (219 mg, 0.35 mmol) was subsequently added as a solid, producing a light brown/green solution that was refluxed for 12 h. The mixture was then plugged through a pad of silica gel and concentrated in vacuo. Purification of the residue via distillation under reduced pressure at 125 °C afforded the desired ester in 75% yield.

Reference： [1]Location in patent: experimental part Cran, John W.; Krafft, Marie E.; Seibert, Kimberly A.; Haxell, Thomas F.N.; Wright, James A.; Hirosawa, Chitaru; Abboud, Khalil A. [Tetrahedron, 2011, vol. 67, # 51, p. 9922 - 9943]

55
[ 625-33-2 ]
[ 2695-47-8 ]
[ 114140-77-1 ]

Yield	Reaction Conditions	Operation in experiment
28%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Inert atmosphere; Reflux;	6.9. Synthesis of compounds 57, 58, 67 and 68: general procedure General procedure: A flame-dried round-bottom flask equipped with reflux condenser was charged with 5-bromo-1-pentene (1.04 g, 7 mmol), 3-penten-2-one (2.1 mL, 7 mmol), and dichloromethane (35 mL). Grubbs second generation catalyst22 (219 mg, 0.35 mmol) was subsequently added as a solid, producing a light brown/green solution that was refluxed for 12 h. The mixture was then plugged through a pad of silica gel and concentrated in vacuo. Purification of the residue via distillation under reduced pressure at 125 °C afforded the desired ester in 75% yield.

Reference： [1]Location in patent: experimental part Cran, John W.; Krafft, Marie E.; Seibert, Kimberly A.; Haxell, Thomas F.N.; Wright, James A.; Hirosawa, Chitaru; Abboud, Khalil A. [Tetrahedron, 2011, vol. 67, # 51, p. 9922 - 9943]

56
[ 625-33-2 ]
[ 174619-42-2 ]
[ 874337-87-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Inert atmosphere; Reflux;	6.7.2. Cross-metathesis General procedure: A flame-dried round-bottom flask equipped with reflux condenser was charged with alkylated malonate (2.14 g, 7 mmol), 3-penten-2-one (2.1 mL, 7 mmol), and dichloromethane (35 mL). Grubbs second generation catalyst22 (219 mg, 0.35 mmol) was subsequently added as a solid, producing a light brown/green solution, which was refluxed for 12 h. The mixture was then plugged through a pad of silica gel and concentrated in vacuo. Purification of the residue via distillation under reduced pressure at 125 °C afforded the desired ester in 48% yield.

Reference： [1]Location in patent: experimental part Cran, John W.; Krafft, Marie E.; Seibert, Kimberly A.; Haxell, Thomas F.N.; Wright, James A.; Hirosawa, Chitaru; Abboud, Khalil A. [Tetrahedron, 2011, vol. 67, # 51, p. 9922 - 9943]

57
[ 33177-29-6 ]
[ 625-33-2 ]

Yield	Reaction Conditions	Operation in experiment
59.7%	In water at 179.84℃; Inert atmosphere;	3 The decarboxylation of DHHMP (2) to PO (7) was performed in a pressurized (500 psi) upflow reactor, using 2 wt % DHHMP in water as the feed (0.04 mL/min) and He as the carrier gas (14 cc (STP)/min). Decomposition of DHHMP in water was noted to occur across a temperature range of 343-543 K. The molar ratio of CO2 to converted DHHMP was close to 1:1 in all runs. In addition to CO2, PO was the only other product observed. Due to low reactant and product concentrations, and reactant feed rate, the overall carbon balance did not close completely. At 100% conversion of DHHMP, 60% molar yield to PO was noted
	With Amberlyst 70 In water at 99.84℃; for 4h; Inert atmosphere; Flow reactor;

Reference： [1]Current Patent Assignee: WARF (in: University of Wisconsin); UNIVERSITY OF WISCONSIN SYSTEM - US2012/116119, 2012, A1 Location in patent: Page/Page column 6
[2]Chia, Mei; Haider, M. Ali; Pollock, Gerald; Kraus, George A.; Neurock, Matthew; Dumesic, James A. [Journal of the American Chemical Society, 2013, vol. 135, # 15, p. 5699 - 5708]

58
[ 625-33-2 ]
[ 936641-27-9 ]
C₁₉H₂₀O [ No CAS ]
[ 1374988-88-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With C₅₀H₆₈Cl₂O₄Rh₂; caesium carbonate In 1,4-dioxane; water at 70℃; for 4h; optical yield given as %ee; enantioselective reaction;	4.3. Typical procedure for the rhodium-catalyzed asymmetric 1,4-addition (entry 12 in Table 1) General procedure: To a solution of [RhCl((R)-L3)]2 (5.0 mg, 10 μmol of Rh, 5 mol % Rh), Cs2CO3 (97.7 mg, 0.30 mmol), and (E)-1,2-diphenylethenylboronic acid 1 (89.6 mg, 0.40 mmol) in dioxane (1.0 mL) was added 2-cyclohexenone 2a (19.2 mg, 0.20 mmol) and H2O (50 μL). After stirring at 70 °C for 4 h, the reaction mixture was diluted with Et2O (1.0 mL), and filtered through a pad of silica gel. The plug was washed with Et2O (30 mL) and the combined filtrates were concentrated on a rotary evaporator. The residue was purified by preparative TLC on silica gel with hexane/EtOAc (3/1) to give 3a (54.5 mg, 99% yield). The data for 3a, 3b, 3c, 3d, and 3i have already been reported.7

Reference： [1]Location in patent: experimental part Sasaki, Keigo; Hayashi, Tamio [Tetrahedron Asymmetry, 2012, vol. 23, # 5, p. 373 - 380]

59
[ 496-15-1 ]
[ 625-33-2 ]
[ 1343287-47-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium fluoride on basic alumina In dichloromethane at 20℃; for 24h;	4.2. General procedure of Lewis acid/base catalyzed Michael addition of indoline with α,β-unsaturated systems General procedure: To a solution of indoline (1.0 mmol) and Michael acceptor (1.0 mmol) in CH2Cl2 (10 mL) was added Lewis acid/base (0.1 mmol). The mixture was stirred until the starting material disappeared (TLC, hexane/ethyl acetate). After evaporation of the solvent, the crude product was dissolved with EtOAc (40 mL) and the organic phase was washed with water (2×20 mL). The EtOAc extract was dried over Na2SO4, filtered, evaporated in vacuo, and the compound was purified by silica gel column chromatography (hexane/ethyl acetate).

Reference： [1]Location in patent: experimental part Kilic, Haydar; Bayindir, Sinan; Erdogan, Esra; Saracoglu, Nurullah [Tetrahedron, 2012, vol. 68, # 27-28, p. 5619 - 5630]

60
[ 627-27-0 ]
[ 625-33-2 ]
[ 1344301-72-9 ]

Yield	Reaction Conditions	Operation in experiment
27%	With sulfuric acid at 0 - 20℃;	4 Intermediate 12: 2,2-diethyloxan-4-ol To a mixture of 3-butene-l-ol (19.8 ml; 233 mmol) and 3-pentenone (12.3 ml; 116 mmol) was added 75% sulfuric acid (19.8; 334 mmol; prepared by diluting 79 ml of cone, sulfuric acid to 100 ml with distilled water) drop-wise at 0 °C. The reaction was allowed to warm to room temperature and stirred overnight. Water (70 ml) was added to the mixture then neutralized with NaOH (pellets) to pH 8 and extracted with diethyl ether (3x150 ml). The ether extract was washed with an aqueous sodium bisulfite solution (40 ml), dried over K2C03 and the ether evaporated in vacuo. The residue was distilled under reduced pressure to give 2,2-diethyloxan-4-ol (4.89 g, 27%, B. Pt. 65-70 °C at 1mm Hg).1H NMR (400 MHz, CDC13) δ 4.04 - 3.86 (m, 1H), 3.84 - 3.66 (m, 1H), 3.65 - 3.38 (m, 1H), 2.06 - 1.95 (m, 1H), 1.92 - 1.76 (m, 2H), 1.78 - 1.63 (m, 1H), 1.63 - 1.50 (m, 1H), 1.51 - 1.31 (m, 3H), 1.28 - 1.10 (m, 1H), 0.92 - 0.68 (m, 6H)
27%	With sulfuric acid In water at 0 - 20℃;	4 Intermediate 12: 2,2-diethyloxan-4-olTo a mixture of 3-butene-1-ol (19.8 ml; 233 mmol) and 3-pentenone (12.3 ml; 116 mmol) was added 75% sulfuric acid (19.8; 334 mmol; prepared by diluting 79 ml of conc. sulfuric acid to 100 ml with distilled water) drop-wise at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. Water (70 ml) was added to the mixture then neutralized with NaOH (pellets) to pH 8 and extracted with diethyl ether (3×150 ml). The ether extract was washed with an aqueous sodium bisulfite solution (40 ml), dried over K2CO3 and the ether evaporated in vacuo. The residue was distilled under reduced pressure to give 2,2-diethyloxan-4-ol (4.89 g, 27%, B. Pt. 65-70° C. at 1 mm Hg).1H NMR (400 MHz, CDCl3) δ 4.04-3.86 (m, 1H), 3.84-3.66 (m, 1H), 3.65-3.38 (m, 1H), 2.06-1.95 (m, 1H), 1.92-1.76 (m, 2H), 1.78-1.63 (m, 1H), 1.63-1.50 (m, 1H), 1.51-1.31 (m, 3H), 1.28-1.10 (m, 1H), 0.92-0.68 (m, 6H).

Reference： [1]Current Patent Assignee: TREVENA INC - WO2017/106547, 2017, A1 Location in patent: Paragraph 0208; 0209; 0210
[2]Current Patent Assignee: TREVENA INC - US2012/245181, 2012, A1 Location in patent: Page/Page column 27

61
[ 617-86-7 ]
[ 625-33-2 ]
[ 57137-75-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,2-bis-(diphenylphosphino)ethane In neat (no solvent) at 20℃; for 6h; Inert atmosphere; diastereoselective reaction;	Representative Procedure for the (Z)-Selective 1,4-Hydrosilylation of Enone (1a) with Triethylsilane General procedure: A flask was charged with [Rh(cod)2]BF4 (10.2 mg, 0.025 mmol) and DPPE (10.0 mg, 0.025 mmol), and then evacuated and filled with argon. To the flask were added 3-nonen-2-one (1a) (701 mg, 5 mmol) and triethylsilane (640 mg, 5.5 mmol). The mixture was stirred under room temperature for 1 h. The progress of the reaction was monitored by GLC. Aluminium oxide 90 (active basic activity stage 1, 0.063-0.200 mm) column chromatography of the residue gave 2a (n-hexane, 1.218 g, 4.75 mmol, 95% yield). The stereoisomeric ratio of 2a was determined by 1H NMR.

Reference： [1]Onodera, Gen; Hachisuka, Ryosuke; Noguchi, Tomomi; Miura, Hiroki; Hashimoto, Toru; Takeuchi, Ryo [Tetrahedron Letters, 2014, vol. 55, # 2, p. 310 - 313]

62
[ 61550-02-5 ]
[ 625-33-2 ]
C₉H₁₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With [Cu((S,S)-(C₆H₅CHCH₂OCN)2C(CH₃)2)](CF₃SO₃)2; 1,1,1,3',3',3'-hexafluoro-propanol In toluene at 20℃; for 5h;

Reference： [1]Fraile, Jose M.; Garcia, Nuria; Herrerias, Clara I. [ACS Catalysis, 2013, vol. 3, # 12, p. 2710 - 2718]

63
[ 625-33-2 ]
[ 374-14-1 ]
C₈H₉F₅N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 2,2,3,3,3-pentafluoropropylamine hydrochloride With sodium nitrite In dichloromethane; water at 0℃; for 0.166667h; Stage #2: 3-penten-2-one In dichloromethane; water at 20℃; for 168h; regioselective reaction;

Reference： [1]Mykhailiuk, Pavel K. [Chemistry - A European Journal, 2014, vol. 20, # 17, p. 4942 - 4947]

64
[ 625-33-2 ]
[ 75-52-5 ]
(R)-4-methyl-5-nitropentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 9-epi-9-amino-9-deoxyquinine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; benzoic acid at 40℃; for 144h; enantioselective reaction;	2. General procedure for the asymmetric Michael reaction: General procedure: 9-amino-epi-quinine 4 (6.5 mg, 0.04 mmol), α,β-unsaturated enones (0.2 mmol) and benzoic acid (9.9 mg, 0.08 mmol) were stirred in redistilled nitromethane at 40 °C. After due reaction time, the reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography onsilica gel (EtOAc/petroleum ether) to afford the desired Michael adduct. The enantiomeric excess was determined by HPLC analysis on chiral column.
80%	With (S)-N<SUP>1</SUP>-cyclohexyl-3,3-dimethylbutane-1,2-diamine; benzoic acid In dichloromethane at 30℃; for 48h; enantioselective reaction;

Reference： [1]Liu, Siyang; Wang, Qingqing; Ye, Ling; Shi, Zhichuan; Zhao, Zhigang; Yang, Xuejun; Ding, Keyi; Li, Xuefeng [Tetrahedron, 2016, vol. 72, # 33, p. 5115 - 5120]
[2]Gu, Xiaodong; Dai, Yuanyuan; Guo, Tingting; Franchino, Allegra; Dixon, Darren J.; Ye, Jinxing [Organic Letters, 2015, vol. 17, # 6, p. 1505 - 1508]

65
[ 625-33-2 ]
[ 20361-10-8 ]
ethyl 3-oxo-1-(4-oxopentan-2-yl)isoindoline-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In acetonitrile at 20℃; for 8h;	General Procedure for K2CO3-Catalyzed Michael Reaction of Isoindolinones 1 General procedure: The unsaturated compound (1.5 eq.) was added at rt to a solution of the iso-indolinone 1 (0.10 mmol) and K2CO3 (0.5 eq., 0.05 mmol) in CH3CN (1 mL). The reaction was stirred until the disappearance of 1 as detected by thin-layer chromatography (TLC), the solvent was evaporated, and the mixture was purified directly on chromatographic column in 8/2 hexane/ethyl acetate, affording the adducts 2 (or 3) in the range of 75-99% yields.

Reference： [1]Scorzelli, Francesco; Di Mola, Antonia; Palombi, Laura; Filosa, Rosanna; Massa, Antonio [Synthetic Communications, 2015, vol. 45, # 13, p. 1552 - 1558]

66
[ 1504-06-9 ]
[ 625-33-2 ]
C₁₄H₁₇NO₂ [ No CAS ]
(R)-3-methyl-3-((S)-4-oxopentan-2-yl)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With Boc-D-Phg-OH; (R,R)-1,2-diphenylethylenediamine In toluene at 20℃; for 24h; stereoselective reaction;

Reference： [1]Wei, Yuan; Wen, Shigang; Liu, Zunwu; Wu, Xinxin; Zeng, Bubing; Ye, Jinxing [Organic Letters, 2015, vol. 17, # 11, p. 2732 - 2735]

67
[ 10604-59-8 ]
[ 625-33-2 ]
4-(1-ethyl-1H-indol-3-yl)pentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dichloro bis(acetonitrile) palladium(II) In 1,2-dichloro-ethane at 30℃; for 6h; regioselective reaction;	Representative Procedure for the Michael Addition of Indoles with Enones General procedure: A mixture of but-3-en-2-one 4b (42 mg, 0.6 mmol), 1H-indole 1a (58.5 mg, 0.5 mmol), PdCl2(MeCN)2 (6.5 mg, 0.025 mmol) in 2 mL of DCE was stirred at at room temperature (30 oC) for appropriate time. Then, solvent was removed under reduced pressure, and the mixture was subjected to column chromatography over silica gel (100-200 mesh, eluent: petroleum ether 60-80 oC/ethylacetate 4:1 v/v) to afford a corresponding product 5d as a white solid in 89% (83 mg) isolated yield.

Reference： [1]Mohapatra, Swapna Sarita; Mukhi, Priyabrata; Mohanty, Anuradha; Pal, Satyanarayan; Sahoo, Aditya Omprakash; Das, Debjit; Roy, Sujit [Tetrahedron Letters, 2015, vol. 56, # 42, p. 5709 - 5713]

68
[ 625-33-2 ]
[ 3724-65-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;	Benzoic Acid (3a); Typical Procedure from Acetophenone or Phenylacetylene General procedure: To a mixture of acetophenone (100 mg, 1 equiv) or phenylacetylene (1 equiv) in dioxane (5 mL), Oxone (2 equiv) and TFA (2 equiv) were added. The mixture was then heated to reflux for 10 h and then cooled to r.t. H2O (10 mL) was added and the mixture was extracted with EtOAc (2 × 20 mL). The combined organic layers were treated with sat. NaHCO3 solution and the aqueous layer was poured onto crushed ice and treated with 2 M HCl; a colorless solid precipitated out. The precipitate was filtered off and dried in vacuo to give benzoic acid (3a) after column chromatography (silica gel; EtOAc-hexane, 1:9) as a white crystalline solid; yield: 0.096 g (95%) from 1a; mp 122-123 °C.

Reference： [1]Aravinda Kumar; Venkateswarlu, Vunnam; Vishwakarma, Ram A.; Sawant, Sanghapal D. [Synthesis, 2015, vol. 47, # 20, p. 3161 - 3168]

69
[ 625-33-2 ]
[ 98-80-6 ]
[ 32587-80-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With chlorobis(ethylene)rhodium(I) dimer; [(η⁵-1-bis(3,5-dimethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 9h; Inert atmosphere; enantioselective reaction;
95%	With chlorobis(ethylene)rhodium(I) dimer; C₄₁H₂₄F₁₂O₂P₂; potassium hydroxide In water; toluene at 20℃; for 4h; Inert atmosphere; Schlenk technique; enantioselective reaction;
95%	With chlorobis(ethylene)rhodium(I) dimer; C₄₁H₂₄F₁₂O₂P₂; potassium hydroxide In water; toluene at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	2 Asymmetric addition of phenylboronic acid to 3-penten-2-one Under nitrogen protection, L (5.3 mg, 6.3ymol) was added to a 10 ml Schlenk flask, Μ-dichlorotetraethylene dirhodium (I) (l .2 mg, 3ymol), K0H (27 mg, 0.48 mmol), 0.8 mL of toluene, 0.3 mL of water, Stir at room temperature for 5 minutes. To the system was added phenylboronic acid (4a) (176 mg, 1.44 mmol) 3-penten-2-one (3b) (10 lmg, 1.2 mmol), followed by stirring at room temperature for 0.5 hour. Saturated NaHC03 solution was added to the system, Extracted with AcOEt three times, dried, Spin-dry and fast column chromatography, To give colorless oily liquid (S) -4-phenylpentanone (196 mg, 95% y i eld, & > 99%ee );

91%	With C₁₇H₂₇NO In water; toluene at 100℃; for 12h; Inert atmosphere;
90%	With heterogeneous Rh/Ag bimetallic nanoparticle catalyst immobilized on chiral polymer In water; toluene at 100℃; for 24h; Inert atmosphere; enantioselective reaction;

Reference： [1]Kamikawa, Ken; Tsen, Ya-Yi; Jian, Jia-Hong; Takahashi, Tamotsu; Ogasawara, Masamichi [Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1545 - 1553]
[2]Hu, Shu-Bo; Chen, Zhang-Pei; Zhou, Ji; Zhou, Yong-Gui [Tetrahedron Letters, 2016, vol. 57, # 17, p. 1925 - 1929]
[3]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN106866736, 2017, A Location in patent: Paragraph 0040-0042
[4]Yasukawa, Tomohiro; Miyamura, Hiroyuki; Kobayashi, Shu [Chemical Science, 2015, vol. 6, # 11, p. 6224 - 6229]
[5]Min, Hyemin; Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu [Chemical Science, 2019, vol. 10, # 32, p. 7619 - 7626]

70
[ 625-33-2 ]
[ 4827-64-9 ]
C₁₃H₁₅NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With (S)-N<SUP>1</SUP>-cyclohexyl-3,3-dimethylbutane-1,2-diamine; benzoic acid In ethyl acetate at 20℃; for 72h; stereoselective reaction;

Reference： [1]Fei, Jie; Qian, Qingqing; Sun, Xiaohua; Gu, Xiaodong; Zou, Chuncheng; Ye, Jinxing [Organic Letters, 2015, vol. 17, # 21, p. 5296 - 5299]

71
[ 34989-82-7 ]
[ 625-33-2 ]
C₁₃H₁₅NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With (S)-N<SUP>1</SUP>-cyclohexyl-3,3-dimethylbutane-1,2-diamine; benzoic acid In tetrahydrofuran at 20℃; for 96h; stereoselective reaction;

Reference： [1]Fei, Jie; Qian, Qingqing; Sun, Xiaohua; Gu, Xiaodong; Zou, Chuncheng; Ye, Jinxing [Organic Letters, 2015, vol. 17, # 21, p. 5296 - 5299]

72
[ 625-33-2 ]
[ 135082-85-8 ]
[ 110-16-7 ]
2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.8%	Stage #1: 3-penten-2-one; 2,2-dimethyl-2H-1-benzopyran-6-amine In propan-1-ol; water for 2h; Stage #2: maleic acid In methanol; ethyl acetate; toluene at 50℃;	1 Production of 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline maleate REFERENCE SYNTHESIS EXAMPLE 1 Production of 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline maleate N-(2,2,-dimethyl-2H-chromen-6-yl)acetamide (199.38 g, 0.918 mol), 1-propanol (800 g), and hydrochloric acid (288 g) were mixed and heated to reflux at 90° C. to 95° C. for 5 hours. The mixture was cooled to room temperature, iron chloride (anhydrous) (400 g, 2.49 mol) was added, and the mixture was heated to 90° C. To the mixture, 3-penten-2-one (140 g, 1.66 mol) was added dropwise and the mixture was heated for 2 hours. The mixture was cooled to room temperature, toluene (1,100 g) and water (1,399 g) were added, and the mixture was separated. To the obtained organic phase, a 16% sodium carbonate aqueous solution (2,200 g) and water (901 g) were added, and the mixture was separated. To the obtained organic phase, activated carbon (10 g) was added, and the mixture was stirred and filtrated. From the filtrate, the solvent was evaporated, and the residue was dried and solidified. The residue was dissolved in ethyl acetate (801 g) and toluene (108 g), and the mixture was heated to 50° C. To the mixture, a solution of maleic acid (85.5 g, 0.737 mol) dissolved in methanol (200 g) was added dropwise. The mixture was cooled to 20° C., and the precipitated crystal was collected by filtration, washed with ethyl acetate (201 g), and dried under reduced pressure at 50° C. to obtain 204.77 g (yield: 62.8%) of 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline maleate as a yellow solid. Appearance: yellow solid 1H-NMR (CDCl3, TMS) δ(ppm): 1.53 (6H, s), 2.76 (3H, s), 2.91 (3H, s), 6.09 (1H, d, J=9.9 Hz), 6.40 (2H, s), 6.63 (1H, d, J=9.9 Hz), 7.30 (2H, s), 8.09 (1H, s)

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2015/266887, 2015, A1 Location in patent: Paragraph 0088

73
[ 625-33-2 ]
dimethyl 2-(pent-4-en-1-yl)malonate [ No CAS ]
dibenzyl (2S)-2-(2-oxopropyl)cyclopentane-1,1-dicarboxylate [ No CAS ]
dibenzyl (2R)-2-(2-oxopropyl)cyclopentane-1,1-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63 % ee	Stage #1: 3-penten-2-one; dimethyl 2-(pent-4-en-1-yl)malonate With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 20℃; for 16h; Inert atmosphere; Stage #2: With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea In toluene for 24h; Inert atmosphere; Overall yield = 76 %; Overall yield = 15 mg; enantioselective reaction;	Dibenzyl (2S)-2-(2-Oxopropyl)cyclopentane-1,1-dicarboxylate (3m; Table 2, Entry 13) General procedure: Dibenzyl (2S)-2-(2-Oxopropyl)cyclopentane-1,1-dicarboxylate (3m; Table 2, Entry 13) Slightly yellow oil; yield: 15.0 mg (76%); [α]D20 -1 7. 0 (c 1 . 0,CHCl3).HPLC [Chiralpak OJ-H, i-PrOH-hexane (5:95); flow rate: 0.6mL/min, λ = 210 nm]: tminor = 90.5 min, tmajor = 76.3 min, ee = 63%. 1H NMR (500 MHz, CDCl3): δ = 7.33-7.26 (m, 10 H), 5.16-5.05(m, 4 H), 2.90-2.89 (m, 1 H), 2.76 (dd, J = 3.0, 17.5 Hz, 1 H), 2.37-2.36 (m, 2 H), 2.19 (dd, J = 11.0, 17.5 Hz, 1 H), 2.12-2.06 (m, 1 H),1.98 (s, 3 H), 1.82-1.79 (m, 1 H), 1.66-1.65 (m, 1 H), 1.33-1.31 (m,1 H).13C NMR (125 MHz, CDCl3): δ = 207.5, 171.8, 171.3, 135.8, 135.6,128.8 2, 128.7 2, 128.6 2, 128.5 2, 128.3 2, 67.2, 67.1,62.9, 45.4, 42.1, 34.3, 31.2, 30.2, 22.9.HRMS (ES): m/z [ M + N a ]+ calcd for C24H26NaO5: 417.1678;found: 417.1695.

Reference： [1]Zhang, Yinan; Song, Xixi; Chen, Xiaobei; Song, Aiguo; Zhang, Shilei; Wang, Wei [Synthesis, 2014, vol. 46, # 19, p. 2601 - 2607]

74
[ 625-33-2 ]
[ 27607-77-8 ]
[ 81802-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at -8 - 0℃; for 0.25h;	39.1 Step 1 : To a solution of 3-penten-2-one (5 mL, 51.2 mmol) and triethylamine (15.71 mL, 113 mmol) in CH2CI2 (125 mL) at -8 °C (internal) was added trimethylsilyl trifluoromethanesulfonate (10.23 mL, 56.4 mmol) at such a rate to keep the internal temperature below 0 °C. The reaction mixture was stirred for 15 minutes at about -5°C and then was allowed to warm to ambient temperature, when LC/MS indicated complete reaction. The reaction mixture was washed successively with water (200 mL), saturated NaHC03 (200 mL), 10%> CuS04 (200 mL x 2) and brine (200 mL). The organic fraction was then dried over Na2S04 and concentrated to yield (E)-trimethyl(penta-l ,3-dien-2-yloxy)silane (6.92 g) which used in next step without further purification.

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS - WO2016/69891, 2016, A1 Location in patent: Page/Page column 180

75
[ 625-33-2 ]
[ 1165952-91-9 ]
1-[(1S*,2S*,3R*,4R*)-3-methylbicyclo[2.2.2]oct-5-en-2-yl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethylaluminum dichloride In toluene at 0℃; for 3h;	5.2.1 1-((1S,4R,7S,8R)-8-Methylbicyclo[2.2.2]oct-2-en-7-yl)ethanone (11) A flame-dried 1L round-bottom flask was charged with 1,4-cyclohexadiene (10) (9.8mL, 0.10mol) and penten-2-one ( 9) (10.0mL, 0.10mol, 70% purity). Anhydrous PhMe (0.20L, 0.5M) was added and the flask was cooled in an ice/water bath. EtAlCl2 (113mL, 0.11mol) was then added, the reaction mixture was stirred at 0°C for 3h. Afterward, 1N HCl solution was added slowly to the reaction mixture, until the evolution of gas had ceased. The mixture was extracted with Et2O (3×), and the organic phases were combined and washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to yield crude product. Acetone was added to the residue, the white precipitate formed was removed by filtration through a small plug of Celite and rinsed with acetone. Solvent was removed via rotary evaporation. The obtained yellow oil was subjected to the next step without further purification. 1H NMR (400MHz, CDCl3) δ 6.41-6.33 (m, 1H), 6.10-6.03 (m, 1H), 2.81-2.73 (m, 1H), 2.29-2.22 (m, 1H), 2.10 (s, 3H), 2.03 (dd, J=6.4Hz, 1.8Hz, 1H), 1.91-1.81 (m, 1H), 1.79-1.69 (m, 1H), 1.56-1.46 (m, 1H), 1.34-1.24 (m, 1H), 1.12-1.01 (m, 1H), 1.07 (d, J=6.9Hz, 1H). 13C NMR (100.52MHz, CDCl3) δ 210.0, 136.9, 130.6, 60.6, 36.0, 33.8, 32.9, 28.4, 26.2, 20.0, 18.2.

Reference： [1]Jansone-Popova, Santa; May, Jeremy A. [Tetrahedron, 2016, vol. 72, # 26, p. 3734 - 3747]

76
[ 625-33-2 ]
4-chloropenta-2,4-dien-5-yltrichlorophosphonium hexachlorophosphorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With phosphorus pentachloride In benzene at 20℃; for 24h;	4-Chloropenta-2,4-dien-5-yltrichlorophosphonium hexachlorophosphorate (6). A solution of 3-penten-2-one 1 (2.6 g, 0.03 mol) in 10 mL of benzene was added dropwise to a solution of phosphorus pentachloride (21 g, 0.1 mol) in 150 mL of benzene at room temperature with stirring. The reaction mixture was kept for 24 h at room temperature followed by filtration. The precipitate was washed with benzene and dried in a vacuum. Yield 12.9 g (86%), colorless crystals hydrolyzed in air, mp 122-123°C (decomp.). Found, %: C 12.01; H 1.83; Cl 72.89; P 12.13. C5H6Cl10P2. Calculated, %: C 12.42; H 1.24; Cl 73.50; P 12.84.

Reference： [1]Larina; Komarova; Rozinov [Russian Journal of General Chemistry, 2016, vol. 86, # 3, p. 512 - 514][Zh. Obshch. Khim., 2016, vol. 86, # 3, p. 368 - 370]

77
[ 625-33-2 ]
[ 6258-66-8 ]
(S)-4-(4-chlorobenzylthio)pentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With C38H54ClFeN2O2; In 1,2-dichloro-ethane; at -5℃; for 31h;	General procedure: An oven-dried vial was charged with Fe-salen complex (+)-2 (13.2 mg, 0.02 mmol, 20 mol%) and enone 7 or 15 (0.1 mmol), followed by anhyd DCE (1 mL). The resulting brown suspension was stirred at r.t. for 10 min. The suspension was cooled to -5 C and thiol 6 (0.12 mmol) was added. The mixture was stirred at -5 C for the appropriate time (see Tables 2 and 3) and then concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography (silica gel, 15% hexane-Et2O). The enantiomeric excess of the purified product was determined by HPLC on a Daicel Chiralcel OD, AD, OJ, OD-H or AS-H column.

Reference： [1]Synthesis,2016,vol. 48,p. 2768 - 2780
[2]Green Chemistry,2020,vol. 22,p. 4645 - 4655

78
[ 625-33-2 ]
[ 100-53-8 ]
C₁₂H₁₆OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With C₃₈H₅₄ClFeN₂O₂ In 1,2-dichloro-ethane at -5℃; for 32h; enantioselective reaction;	Asymmetric Sulfa-Michael Addition of Thiols to Acyclic α,β-Unsaturated Ketones Catalyzed by the Fe-Salen Complex (+)-2; General Procedure General procedure: An oven-dried vial was charged with Fe-salen complex (+)-2 (13.2 mg, 0.02 mmol, 20 mol%) and enone 7 or 15 (0.1 mmol), followed by anhyd DCE (1 mL). The resulting brown suspension was stirred at r.t. for 10 min. The suspension was cooled to -5 °C and thiol 6 (0.12 mmol) was added. The mixture was stirred at -5 °C for the appropriate time (see Tables 2 and 3) and then concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography (silica gel, 15% hexane-Et2O). The enantiomeric excess of the purified product was determined by HPLC on a Daicel Chiralcel OD, AD, OJ, OD-H or AS-H column.

Reference： [1]Shaw, Subrata; White, James D. [Synthesis, 2016, vol. 48, # 17, p. 2768 - 2780]

79
[ 625-33-2 ]
[ 108-98-5 ]
C₁₁H₁₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With C₃₈H₅₄ClFeN₂O₂ In 1,2-dichloro-ethane at -5℃; for 34h; enantioselective reaction;	Asymmetric Sulfa-Michael Addition of Thiols to Acyclic α,β-Unsaturated Ketones Catalyzed by the Fe-Salen Complex (+)-2; General Procedure General procedure: An oven-dried vial was charged with Fe-salen complex (+)-2 (13.2 mg, 0.02 mmol, 20 mol%) and enone 7 or 15 (0.1 mmol), followed by anhyd DCE (1 mL). The resulting brown suspension was stirred at r.t. for 10 min. The suspension was cooled to -5 °C and thiol 6 (0.12 mmol) was added. The mixture was stirred at -5 °C for the appropriate time (see Tables 2 and 3) and then concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography (silica gel, 15% hexane-Et2O). The enantiomeric excess of the purified product was determined by HPLC on a Daicel Chiralcel OD, AD, OJ, OD-H or AS-H column.

Reference： [1]Shaw, Subrata; White, James D. [Synthesis, 2016, vol. 48, # 17, p. 2768 - 2780]

80
[ 625-33-2 ]
[ 36635-61-7 ]
[ 18818-30-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride In diethyl ether; hexane; dimethyl sulfoxide at 20℃; for 1h;
79%	With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 20℃; for 1h;

Reference： [1]Wang, Pengzhi; Chau Nguyen, Khiem; Lindsey, Jonathan S. [Journal of Organic Chemistry, 2019, vol. 84, # 17, p. 11286 - 11293]
[2]Knowles, Jonathan P.; Booker-Milburn, Kevin I. [Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11429 - 11434]

81
[ 625-33-2 ]
N-(4-hydroxy-2,2-dimethylchroman-6-yl)butylamide [ No CAS ]
[ 865478-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(4-hydroxy-2,2-dimethylchroman-6-yl)butylamide With hydrogenchloride In ethanol; water at 77 - 81℃; for 13h; Stage #2: 3-penten-2-one With iron(III) chloride In ethanol; water at 30 - 85℃; for 4h;	7 The compound (3’) (140 g, 0.53 mol; (which is the amount of dried crystal; 177 gina case of wet crystal of the compound (3’))) obtained in Example 6 and ethanol (662 g) were mixed, and the mixture was heated to 77° C. Concentrated hydrochloric acid (277 g, 2.66 mol) was added, and the mixture was stirred at a temperature range of 80° C. to 81° C. for 13 hours, and then cooled to 30° C.10162] To the obtained reaction solution, iron (III) chloride (259 g, 1.60 mol) was added, and the mixture was heated to 82° C. Further, 3-penten-2-one (76.0 g, 0.90 mol) was added, and the mixture was stirred at a temperature range of 84° C. to 85°C. for 4 hours. The mixture was then cooled, toluene (700 g) and water (420 g) were added, and the mixture was stirred and then subjected to phase separation to obtain an organic phase. To the obtained organic phase, an aqueous solution (1,343 g) of 17% potassium carbonate was added, and the mixture was stirred and further subjected to phase separation to obtain an organic phase. To the resulting aqueous phase, toluene (700 g) was added, and the mixture was stirred and then subjected to phase separation to obtain an organic phase. All the organic phases thus obtained were combined, and water (700 g) was added. The mixture was stirred and then subjected to phase separation to obtain an organic phase. To the obtained organic phase, activated carbon (7.00 g) was added, and the mixture was stirred for 1 hour, and filtered through Celite as a filter aid. Further, the Celite was washed with toluene (140 g) and the filtrate was obtained. The filtrate afierthe filtrationwas concentrated to obtain 560g of solution of the compound (6) in toluene (purity: 85.07%). (Here, the purity was calculated excluding the peak of toluene.)

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2016/168161, 2016, A1 Location in patent: Paragraph 0161; 0162

82
[ 625-33-2 ]
[ 135082-85-8 ]
[ 865478-53-1 ]

Yield	Reaction Conditions	Operation in experiment
0.13 g	With hydrogenchloride; iron(III) chloride In propan-1-ol; water at 76 - 95℃; for 3h;	5 Method for Producing compound (6): 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline The compound (5) (0.18 g, 1.00 mmol) obtained in Example 5, n-propanol (1.80 g), concentrated hydrochloric acid (0.38 g, 3.65 mmol), and iron (III) chloride (0.50 g, 3.08 mmol) were mixed, and the mixture was heated to 76° C. Further, 3-penten-2-one (0.19 g, 1.83 mmol) was added, and the mixture was stirred at a temperature range of 80° C. to 95° C. for 3 hours. After then, an aqueous sodium carbonate solution and ethyl acetate were added and the mixture was subjected to phase separation to obtain an organic phase. The resulting aqueous phase was further subjected to phase separation with ethyl acetate to obtain an organic phase. All the obtained organic phases were combined, concentrated, and purified by column chromatography, to obtain 0.13 g of compound (6). Compound (6)MASS: 240 (M+1). ‘H-NMR (CDC13, TMS):ö(ppm): 1.49 (6H, s), 2.54 (3H, s), 2.62 (3H, s), 5.86 (1H, d,J=9.9 Hz), 6.56 (1H, d, J=9.9 Hz), 7.01 (1H, s), 7.20 (1H, s),7.60 (1H, s)Melting Point: 64° C.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2016/168161, 2016, A1 Location in patent: Paragraph 0153; 0154; 0155; 0156

83
[ 625-33-2 ]
[ 73183-34-3 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With methanol; copper nanoparticles on black carbon In toluene at 20℃; for 4h;	4.4.9. Experimental procedures for examples described in Table 2 CuNPs/CB (2 mg, 1.25 mol %), B2(pin)2 (0.22 mmol), 1 (0.2 mmol) were added to a 25 mL oven-dried Schlenk tube in air. Then toluene (1 mL) was added with a syringe. The resulting reaction mixture was stirred at room temperature for 4 h. The reaction mixture was then diluted with Et2O, filtered through silica gel with copious washings (Et2O or EtOAc), concentrated, and purified by column chromatography.

Reference： [1]Zhou, Xin-Feng; Sun, Yu-Yang; Wu, Ya-Dong; Dai, Jian-Jun; Xu, Jun; Huang, Yu; Xu, Hua-Jian [Tetrahedron, 2016, vol. 72, # 37, p. 5691 - 5698]

84
[ 625-33-2 ]
[ 759-02-4 ]
[ 56704-25-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With ammonium acetate; caesium carbonate In acetonitrile at 60℃; for 16h; regioselective reaction;

Reference： [1]Song, Zhidong; Huang, Xin; Yi, Wenbin; Zhang, Wei [Organic Letters, 2016, vol. 18, # 21, p. 5640 - 5643]

85
[ 625-33-2 ]
[ 126-81-8 ]
2-hydroxy-2,4,7,7-tetramethyl-2,3,4,6,7,8-hexahydro-5H-chromen-5-one [ No CAS ]
C₁₃H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91 % ee	With 9-epi-9-amino-9-deoxyquinine; salicylic acid In tetrahydrofuran at 0℃; for 96h; Overall yield = 69 %; enantioselective reaction;	3.2. General Procedure for the Asymmetric Michael Reaction of Cinnamones General procedure: 9-Amino-epi-quinine 3a (6.5 mg, 0.02 mmol), α,β-unsaturated enones (0.12 mmol), dimedone(14.0 mg, 0.1 mmol), and salicylic acid (4.9 mg, 0.04 mmol) were dissolved in THF (1 mL) withoutstirring. Once the solution was cooled down to 0 °C, the reaction mixture was stirred for 96 h.After the solvent was removed in vacuo, the residue was purified by flash chromatography on silicagel (EtOAc/petroleum ether) to afford the desired 3,4-dihydropyran.

Reference： [1]Wang, Qingqing; Wang, Wei; Ye, Ling; Yang, Xuejun; Li, Xinying; Zhao, Zhigang; Li, Xuefeng [Molecules, 2017, vol. 22, # 7]

86
[ 56434-57-2 ]
[ 625-33-2 ]
methyl (S)-3-oxo-2-(4-oxopentan-2-yl)-2,3-dihydrobenzofuran-2-carboxylate [ No CAS ]
C₁₅H₁₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 % de	Stage #1: 3-oxo-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester With C₄₂H₃₃N₃O₂; copper(II) bis(trifluoromethanesulfonate) In toluene at 20℃; for 0.166667h; Stage #2: 3-penten-2-one In toluene at 20℃; for 8h; Overall yield = 90 %; stereoselective reaction;	34 Example 1 General procedure: A complex of 0.02 mmol of oxazoline ligand (6)-an and copper trifluoromethanesulfonate is added, 3-oxo -2,3-dihydrobenzofuran-2-carboxylate (0.2 mmol)) adding into a 10 ml test tube, adding 4 ml of toluene to dissolve, and stirring at room temperature for 10 minutes, and adding the alpha, beta-unsaturated ketene as shown in the reaction formula 2A into the system by a sample feeding needle2Mmol), carrying out stirring reaction at room temperature for 8 hours, concentrating the reaction solution under reduced pressure, and separating by using a silica gel chromatography column, wherein the volume ratio of petroleum ether to ethyl acetate is 1-10: 1, and gradient elution is carried out on the eluent by taking eluent as an eluent, collecting eluant and evaporating the solvent to obtain an yellow liquid product (yield of 81%))

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN107188874, 2017, A Location in patent: Paragraph 0024-0027; 0091-0093

87
[ 2075-46-9 ]
[ 625-33-2 ]
C₈H₁₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.2%	Stage #1: 4-nitro-1H-pyrazole; 3-penten-2-one In ethanol at 140℃; for 4h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃;	A21b Preparation of intermediate 1 06b: In a sealed tube, 4-nitro-1H-pyrazole (3.898 g, 34.475 mmol) and 3-penten-2-one (6.729mL, 0.862 g/mL, 68.95 1 mmol) in EtOH (40.26 mL) were stirred at 140°C for 4 hours.After cooling down to rt, sodium borohydride (2.609 g, 68.951 mmol) was added portionwise. The reaction mixture was stirred at rt overnight.. The reaction mixture was poured onto ice water, acidified with 3N HC1(aq), extracetd with DCM twice, dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified viapreparative LC (Stationary phase: irregular SiOH 15-40jim 80g Grace, Mobile phase:gradient from 80% heptane, 20% EtOAc to 40% heptane, 60% EtOAc, 10% MeOH (2% NH4OH)) to afford intermediate 106b (5.3 g, yield 77.2%)

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2018/2219, 2018, A1 Location in patent: Page/Page column 298

Type	HazMat fee for 500 gram (Estimated)
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CAS No. :	625-33-2	MDL No. :	MFCD00009290
Formula :	C₅H₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LABTWGUMFABVFG-ONEGZZNKSA-N
M.W :	84.12	Pubchem ID :	637920
Synonyms :

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.88
TPSA :	17.07 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.44 cm/s

[ CAS No. 625-33-2 ] {[proInfo.proName]}

Quality Control of [ 625-33-2 ]

Related Doc. of [ 625-33-2 ]

Product Details of [ 625-33-2 ]

Calculated chemistry of [ 625-33-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 625-33-2 ]

Application In Synthesis of [ 625-33-2 ]

[ 625-33-2 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	0.52
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	0.83
Consensus Log Po/w :	0.99

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-0.62
Solubility :	20.0 mg/ml ; 0.238 mol/l
Class :	Very soluble
Log S (Ali) :	-0.45
Solubility :	29.9 mg/ml ; 0.355 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.58
Solubility :	22.0 mg/ml ; 0.261 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling