Name: 4683-50-5|3-Methoxycyclopent-2-enone|98%
Brand: Ambeed
SKU: A912409
Price: 35.0 USD
Availability: InStock
Rating: 90 (25 reviews)

1
[ 4683-50-5 ]
[ 1826-67-1 ]
[ 108264-48-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran at -78℃; for 1h;
68%	In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	Preparation of 3-vinylcyclopent-2-en-1-one (1) Iodine (47 mg, 0.18 mmol) was added to a solution of 1,3-cyclopentanedione (600 mg, 6.12 mmol) in methanol (12 mL) at room temperature and stirred at the same temperature. After 48 h, the resulting solution was concentrated in vacuo. The residual oil was purified by silica gel column chromatography (AcOEt/hexane = 3/1~1/0) to afford 3-methoxycyclopent-2-en-1-one as a light yellow solid (546 mg, 80% yield). To a solution of 3-methoxycyclopent-2-en-1-one (458 mg, 3.6 mmol) in THF (3.6 mL) was added dropwise a solution of a vinyl magnesium bromide (1 M in THF, 4.0 mL, 4.0 mmol) at 0 °C under argon. Once the addition was complete, the resulting solution was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was poured into 1 N HCl aq. at 0 °C. The layers were separated, and the aqueous layer was extracted with AcOEt (3×20 mL). The combined organic layers were washed successively with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (AcOEt/hexane = 28/72) to afford 1 as a colorless oil (267 mg, 68% yield).

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[2]Hyakutake, Ryuichi; Gondo, Naruhiro; Ueda, Yoshihiro; Yoshimura, Tomoyuki; Furuta, Takumi; Kawabata, Takeo [Tetrahedron Letters, 2016, vol. 57, # 12, p. 1321 - 1324]

2
[ 4683-50-5 ]
[ 68236-10-2 ]
[ 192181-83-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sulfuric acid In tetrahydrofuran 1.) THF, 0 deg C; 2.) 30 min;

Reference： [1]Molander, Gary A.; Hiersemann, Martin [Tetrahedron Letters, 1997, vol. 38, # 25, p. 4347 - 4350]

3
[ 14630-40-1 ]
[ 4683-50-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With water In 1,4-dioxane for 12h; Heating;

Reference： [1]Tumer, Seniz U.; Herndon, James W.; McMullen, Leonard A. [Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8394 - 8404]

4
[ 67-56-1 ]
[ 3859-41-4 ]
[ 4683-50-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With iodine at 23℃; for 48h; Inert atmosphere;
96%	With tris(pentafluorophenyl)borate at 20℃;
93%	With iodine at 20℃; for 0.0666667h;

92%	With titanium tetrachloride In dichloromethane at 20℃; for 0.5h;
90%	With phosphorus pentaoxide; silica gel at 20℃; for 0.333333h;
90%	With Al_x Cl_y-ionic liquid-SiO₂-Fe₂O₃ at 20℃; for 0.583333h;
80%	With titanium tetrachloride
80%	With titanium tetrachloride In dichloromethane at 20℃; for 1h;
80%	With iodine at 20℃; for 48h;	Preparation of 3-vinylcyclopent-2-en-1-one (1) Iodine (47 mg, 0.18 mmol) was added to a solution of 1,3-cyclopentanedione (600 mg, 6.12 mmol) in methanol (12 mL) at room temperature and stirred at the same temperature. After 48 h, the resulting solution was concentrated in vacuo. The residual oil was purified by silica gel column chromatography (AcOEt/hexane = 3/1~1/0) to afford 3-methoxycyclopent-2-en-1-one as a light yellow solid (546 mg, 80% yield). To a solution of 3-methoxycyclopent-2-en-1-one (458 mg, 3.6 mmol) in THF (3.6 mL) was added dropwise a solution of a vinyl magnesium bromide (1 M in THF, 4.0 mL, 4.0 mmol) at 0 °C under argon. Once the addition was complete, the resulting solution was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was poured into 1 N HCl aq. at 0 °C. The layers were separated, and the aqueous layer was extracted with AcOEt (3×20 mL). The combined organic layers were washed successively with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (AcOEt/hexane = 28/72) to afford 1 as a colorless oil (267 mg, 68% yield).
67%	With sulfuric acid for 18h; Reflux;
	With iodine at 25℃; for 16h;	7.A Example 7 A; 3 -methoxycyclopent-2-enone; A mixture of 1,3-cyclopentanedione (15.0 g, 153 mmol) and I2 (1.164 g, 4.59 mmol) in methanol (150 mL) was stirred at 25 °C for 16 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with aqueous Na2S203 solution (100 mL), water (100 mL) and brine (100 mL) successively. The organic layer was dried over Na2S04, filtered and concentrated in vacuo. The residue was used in the next step without further purification. LC/MS (ESI) m/z 113 (M+H)+.

Reference： [1]Kats-Kagan, Roman; Herzon, Seth B. [Organic Letters, 2015, vol. 17, # 8, p. 2030 - 2033]
[2]Chandrasekhar; Srinivasa Rao; Ramakrishna Reddy [Synlett, 2005, # 9, p. 1471 - 1473]
[3]Bhosale, Rajesh S.; Bhosale, Sidhanath V.; Bhosale, Sheshanath V.; Wang, Tianyu; Zubaidha [Tetrahedron Letters, 2004, vol. 45, # 39, p. 7187 - 7188]
[4]Clerici, Angelo; Pastori, Nadia; Porta, Ombretta [Tetrahedron, 2001, vol. 57, # 1, p. 217 - 225]
[5]Cui, Zhen-Shui; Zhang, Zhan-Hui; Liu, Shu-Fen [Journal of Chemical Research, 2006, # 6, p. 390 - 392]
[6]Li, Pei-He; Li, Bao-Le; Hu, Hai-Chuan; Zhao, Xiao-Na; Zhang, Zhan-Hui [Catalysis Communications, 2014, vol. 46, p. 118 - 122]
[7]Liang, Huan; Schule, Arnaud; Vors, Jean-Pierre; Ciufolini, Marco A. [Organic Letters, 2007, vol. 9, # 21, p. 4119 - 4122]
[8]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]
[9]Hyakutake, Ryuichi; Gondo, Naruhiro; Ueda, Yoshihiro; Yoshimura, Tomoyuki; Furuta, Takumi; Kawabata, Takeo [Tetrahedron Letters, 2016, vol. 57, # 12, p. 1321 - 1324]
[10]Winkler, Christoph K.; Stueckler, Clemens; Mueller, Nicole J.; Pressnitz, Desiree; Faber, Kurt [European Journal of Organic Chemistry, 2010, # 33, p. 6354 - 6358]
[11]Current Patent Assignee: ABBVIE INC; ABBOTT LABORATORIES INC - WO2012/83170, 2012, A1 Location in patent: Page/Page column 181

5
[ 4683-50-5 ]
(+/-)-5-hydroxy-3-methoxycyclopent-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With pocine pancreatic lipase In phosphate buffer; dimethyl sulfoxide at 20℃; for 36h;

Reference： [1]Demir, Ayhan S.; Sesenoglu, Ozge [Tetrahedron Asymmetry, 2002, vol. 13, # 6, p. 667 - 670]

6
[ 629-04-9 ]
[ 4683-50-5 ]
[ 67100-40-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 1-Bromoheptane With magnesium In tetrahydrofuran Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran at 0 - 20℃;

Reference： [1]Lipshutz, Bruce H.; Servesko, Jeff M.; Petersen, Tue B.; Papa, Patrick P.; Lover, Andrew A. [Organic Letters, 2004, vol. 6, # 8, p. 1273 - 1275]

7
[ 6952-59-6 ]
[ 4683-50-5 ]
[ 849697-79-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 3-cyanobromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexane at -78 - -20℃; for 1.5h;

Reference： [1]McBriar, Mark D.; Guzik, Henry; Xu, Ruo; Paruchova, Jaroslava; Li, Shengjian; Palani, Anandan; Clader, John W.; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian; Weig, Blair [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2274 - 2277] McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

8
[ 4683-50-5 ]
[ 623-00-7 ]
[ 849697-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromobenzenecarbonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexane at -78 - -20℃;

Reference： [1]McBriar, Mark D.; Guzik, Henry; Xu, Ruo; Paruchova, Jaroslava; Li, Shengjian; Palani, Anandan; Clader, John W.; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian; Weig, Blair [Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2274 - 2277]

9
[ 108-36-1 ]
[ 4683-50-5 ]
[ 885323-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,3-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexane at -78 - -20℃;

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

10
[ 4683-50-5 ]
[ 90878-19-6 ]
[ 104804-92-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran at 0℃; for 12h;
	In tetrahydrofuran	19 3-Phenethylcyclopentenone 3-Phenethylcyclopentenone The general procedure for the preparation of substrates using 3-methoxycyclopentenone (1.29 g, 11.5 mmol) and phenethylmagnesium chloride (23 mmol, 1M in THF) gave, afler flash chromatography (4:1 hexanes:ethyl acetate), the title compound as a colorless liquid (2.01 g, 94%). Spectroscopic data were consistent with previously reported data for this compound.4

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]
[2]Current Patent Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGY - US6465664, 2002, B1

11
[ 4683-50-5 ]
[ 2695-47-8 ]
[ 155500-24-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 6-Bromo-1-hexene With magnesium In tetrahydrofuran at 0 - 60℃; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran at 0 - 60℃; for 2h; Inert atmosphere;
2.67 g	Stage #1: 6-Bromo-1-hexene With magnesium In tetrahydrofuran at 60℃; for 12h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran at 0 - 12℃; Further stages.;

Reference： [1]Stang, Erik M.; White, M. Christina [Journal of the American Chemical Society, 2011, vol. 133, # 38, p. 14892 - 14895]
[2]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

12
[ 17640-15-2 ]
[ 4683-50-5 ]
[ 141693-19-8 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: 3-methoxycyclopent-2-enone With lithium hexamethyldisilazane In tetrahydrofuran at -50℃; for 0.5h; Stage #2: methyl cyanoformate In tetrahydrofuran at -50 - 20℃; for 2.5h; Further stages.;

Reference： [1]Liang, Huan; Schule, Arnaud; Vors, Jean-Pierre; Ciufolini, Marco A. [Organic Letters, 2007, vol. 9, # 21, p. 4119 - 4122]

13
[ 4683-50-5 ]
(+/-)-trans-3-(3-hydroxycyclopentyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 8 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

14
[ 4683-50-5 ]
cis-3-(3-hydroxycyclopentyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

15
[ 4683-50-5 ]
3-((1R,3R)-3-Bromo-cyclopentyl)-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: 85 percent / CBr₄; Ph₃P / tetrahydrofuran / 1 h / 0 °C

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

16
[ 4683-50-5 ]
Methanesulfonic acid (1S,3R)-3-(3-cyano-phenyl)-cyclopentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: Et₃N / CH₂Cl₂ / 3 h

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

17
[ 4683-50-5 ]
trans-3-{3-[3-(4-methylpiperazin-1-yl)propylamino]cyclopentyl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: Et₃N / CH₂Cl₂ / 3 h 5.1: 200 mg / K₂CO₃ / various solvent(s) / 18 h / 100 °C

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

18
[ 4683-50-5 ]
cis-3-{3-[3-(4-methylpiperazin-1-yl)propylamino]cyclopentyl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: 85 percent / CBr₄; Ph₃P / tetrahydrofuran / 1 h / 0 °C 5.1: 85 percent / K₂CO₃ / various solvent(s) / 18 h / 100 °C

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

19
[ 4683-50-5 ]
N'-(3-chloro-4-fluorophenyl)-N-[trans-3-(3-cyanophenyl)cyclopentyl]-N-[3-(4-methyl-1-piperazinyl)propyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: Et₃N / CH₂Cl₂ / 3 h 5.1: 200 mg / K₂CO₃ / various solvent(s) / 18 h / 100 °C 6.1: 61 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

20
[ 4683-50-5 ]
N'-(3-chloro-4-fluorophenyl)-N-[cis-3-(3-cyanophenyl)cyclopentyl]-N-[3-(4-methyl-1-piperazinyl)propyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 59 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -20 °C 2.1: 80 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 12 h / 0 - 20 °C 3.1: 68 percent / H₂ / Pd/C / methanol; H₂O / 1 h / 760 Torr 4.1: 85 percent / CBr₄; Ph₃P / tetrahydrofuran / 1 h / 0 °C 5.1: 85 percent / K₂CO₃ / various solvent(s) / 18 h / 100 °C 6.1: 79 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

Reference： [1]McBriar, Mark D.; Guzik, Henry; Shapiro, Sherry; Paruchova, Jaroslava; Xu, Ruo; Palani, Anandan; Clader, John W.; Cox, Kathleen; Greenlee, William J.; Hawes, Brian E.; Kowalski, Timothy J.; O'Neill, Kim; Spar, Brian D.; Weig, Blair; Weston, Daniel J.; Farley, Constance; Cook, John [Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2294 - 2310]

21
[ 4683-50-5 ]
(R)-3-heptylcyclopentanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran 1.2: 68 percent / tetrahydrofuran / 0 - 20 °C 2.1: copper(I) chloride; sodium methoxide; polymethylhydrosiloxane / (R)-(2,3-methylenedioxy-6-(4-MeO-3,5-tBu₂-C₆H₂)2P-C₆H₂)2 / toluene / -78 °C 2.2: 97 percent / toluene / Alkaline hydrolysis

Reference： [1]Lipshutz, Bruce H.; Servesko, Jeff M.; Petersen, Tue B.; Papa, Patrick P.; Lover, Andrew A. [Organic Letters, 2004, vol. 6, # 8, p. 1273 - 1275]

22
[ 4683-50-5 ]
3-(5-hexenyl)cyclopentanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg / tetrahydrofuran / 12 h / 60 °C 1.2: 2.67 g / tetrahydrofuran / 0 - 12 °C 2.1: polymethylhydrosiloxane; NaOt-Bu; (S)-BINAP / CuCl / toluene / 24 h / 15 °C

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

23
[ 4683-50-5 ]
(2R,3R,7S)-7-Hex-5-enyl-2,3-dimethyl-1,4-dioxa-spiro[4.4]nonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Mg / tetrahydrofuran / 12 h / 60 °C 1.2: 2.67 g / tetrahydrofuran / 0 - 12 °C 2.1: polymethylhydrosiloxane; NaOt-Bu; (S)-BINAP / CuCl / toluene / 24 h / 15 °C 3.1: p-toluenesulfonic acid / toluene / 0.5 h / 120 °C

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

24
[ 4683-50-5 ]
Bis-((S)-3-phenethyl-cyclopent-1-enyloxy)-diphenyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 12 h / 0 °C 2: 78 percent / NaOt-Bu; (S)-p-tol-BINAP / CuCl / toluene / 4 h / -78 °C

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

25
[ 4683-50-5 ]
[ 102776-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 12 h / 0 °C 2: 84 percent / polymethylhydrosiloxane; NaOt-Bu; (S)-p-tol-BINAP / CuCl / toluene / 24 h / 10 °C

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

26
[ 4683-50-5 ]
[ 288304-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg / tetrahydrofuran / 12 h / 60 °C 1.2: 2.67 g / tetrahydrofuran / 0 - 12 °C 2.1: polymethylhydrosiloxane; NaOt-Bu; (S)-BINAP / CuCl / toluene / 24 h / 15 °C

Reference： [1]Moritani, Yasunori; Appella, Daniel H.; Jurkauskas, Valdas; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6797 - 6798]

27
[ 4683-50-5 ]
[ 114614-91-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

28
[ 4683-50-5 ]
[ 114614-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 42 percent / KH / diethyl ether / 3 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

29
[ 4683-50-5 ]
[ 114614-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

30
[ 4683-50-5 ]
[ 114615-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: tetrahydrofuran / 3 h / Ambient temperature 5: 86 percent / HF / acetonitrile; H₂O / 192 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

31
[ 4683-50-5 ]
[ 114615-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: tetrahydrofuran / 4 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

32
[ 4683-50-5 ]
[ 114673-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 1.) toluene, roomtemp., 36 h; 2.) CH₂Cl₂, 0 deg C, 0.5 h 4: 75 percent / acetic acid / tetrahydrofuran; H₂O / 72 h / Ambient temperature
	Multi-step reaction with 5 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: 84 percent / toluene / 36 h / Ambient temperature 5: 75 percent / acetic acid / tetrahydrofuran; H₂O / 72 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[2]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

33
[ 4683-50-5 ]
[ 114615-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 1.) toluene, roomtemp., 36 h; 2.) CH₂Cl₂, 0 deg C, 0.5 h 4: 75 percent / acetic acid / tetrahydrofuran; H₂O / 72 h / Ambient temperature 5: 95 percent / Ag₂O, K₂CO₃ / CHCl₃ / 96 h / Ambient temperature
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: 73 percent / toluene / 24 h / Ambient temperature
	Multi-step reaction with 6 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: 84 percent / toluene / 36 h / Ambient temperature 5: 75 percent / acetic acid / tetrahydrofuran; H₂O / 72 h / Ambient temperature 6: 95 percent / Ag₂O, K₂CO₃ / CHCl₃ / 96 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[2]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[3]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

34
[ 4683-50-5 ]
[ 114615-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: tetrahydrofuran / 4 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

35
[ 4683-50-5 ]
[ 114615-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 42 percent / tetrahydrofuran / 4 h / Ambient temperature
	Multi-step reaction with 5 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: tetrahydrofuran / 3 h / Ambient temperature 5: 100 percent / HF / acetonitrile; H₂O / 96 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[2]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

36
[ 4683-50-5 ]
[ 114615-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 42 percent / KH / diethyl ether / 3 h / Ambient temperature 4: tetrahydrofuran / 5 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

37
[ 4683-50-5 ]
[ 114615-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 42 percent / KH / diethyl ether / 3 h / Ambient temperature 4: tetrahydrofuran / 5 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

38
[ 4683-50-5 ]
[ 114615-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: tetrahydrofuran / 3 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

39
[ 4683-50-5 ]
[ 114615-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: tetrahydrofuran / 3 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

40
[ 4683-50-5 ]
[ 114615-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 1.) toluene, roomtemp., 36 h; 2.) CH₂Cl₂, 0 deg C, 0.5 h

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

41
[ 4683-50-5 ]
[ 114673-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 1.) toluene, roomtemp., 36 h; 2.) CH₂Cl₂, 0 deg C, 0.5 h
	Multi-step reaction with 4 steps 1: 98 percent / tetrahydrofuran / 1 h / -78 °C 2: 84 percent / diisobutylaluminum hydride, NaF, H₂O / diethyl ether / 0.5 h / 0 °C 3: 89 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 4: 84 percent / toluene / 36 h / Ambient temperature

Reference： [1]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]
[2]Fisher,M.J.; Hehre,W.J.; Kahn,S.D. [Journal of the American Chemical Society, 1988, vol. 110, p. 4625]

42
[ 4683-50-5 ]
[ 32916-51-1 ]
[ 70640-08-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 3-methoxycyclopent-2-enone; cyclopentylmagnesium chloride With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex In tetrahydrofuran; diethyl ether at -78 - 20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water for 0.166667h; Inert atmosphere;	3-Cyclopentyl-2-cyclopenten-1-one (2a): To a stirred suspension of 800mg of copper bromide dimethylsulfide in 100ml of THF equilibrated to -78°C, were added in series 24ml of 2.0M cyclopentylmagnesium chloride in diethyl ether and 8ml of HMPA under inert atmosphere. To the mixture was added a solution of 5.4ml of TMSCl and 4.3g of 3-methoxy-2-cyclopenten-1-one in 20ml of THF. The reaction mixture was slowly warmed to room temperature and stirred for 3h, to which was added 50ml of 10% aqueous HCl. The resulting reaction mixture was stirred for another 10 min and subjected to extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. Then the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=3:1) to yield 4.5g (78%) of 3-cyclopentyl-2-cyclopenten-1-one as an oil. 1H NMR (CDCl3, 300MHz): δ 5.94 (m, 1H), 2.82 (m, 1H), 2.61 (m, 2H), 2.41 (m, 2H), 1.96 (m, 2H), 1.77-1.5 (m, 6H); MS (EI): 150 (M+).
	With chloro-trimethyl-silane; copper bromide dimethylsulfide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -78 - 20℃; for 3h;	1.1 Example 1: 3-cyclopentyl-2-(4-fluorophenyl)-2-cyclopenten-l -one oxime:; The titled compound was prepared according to the four step procedure as described below.; STEP 1 (Synthesis of 3-cyclopentyl-2-cvclopenten-l-one):; To a stirred suspension of 800 mg copper bromide dimethylsulfide in 100 ml tetrahydrofuran (THF) equilibrated to -78 0C, were added in series 24 ml 2.0 M cyclopentylmagnesium chloride in diethyl ether and 8 ml hexamethylphosphoramide (HMPA) under inert atmosphere. To the mixture was added a solution of 5.4 ml trimethylsilyl chloride (TMSCl) and 4.3 g 3-methoxy-2-cyclopenten-l-one in 20 ml THF. The reaction mixture was slowly warmed to room temperature and stirred for 3 hours, to which was added 50 ml 10 % aqueous HCl. The resulting reaction mixture was stirred for another 10 min and subjected to extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. Then the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate = 3:1) to yield 4.5 g of 3-cyclopentyl- 2-cycloρenten-l-one as an oil. 1H NMR (CDCl3, 300MHz): δ 5.94 (m, IH), 2.82 (m, IH), 2.61 (m, 2H), 2.41 (m, 2H), 1.96 (m, 2H), 1.77-1.5 (m, 6H).

Reference： [1]Kim, Yeonjoon; Hong, Yong Deog; Joo, Yung Hyup; Woo, Byung Young; Kim, Sun-Young; Koh, Hyun Ju; Park, Miyoung; Byoun, Kyoung Hee; Shin, Song Seok [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 13, p. 2807 - 2810]
[2]Current Patent Assignee: AMOREPACIFIC CORP. - WO2006/59867, 2006, A1 Location in patent: Page/Page column 11-12

43
[ 110-18-9 ]
[ 4683-50-5 ]
[ 295788-93-1 ]
[ 296764-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium In tetrahydrofuran	3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one 3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one 1,3-Bis(methoxymethoxy)-4-bromobenzene (1.0 g) was dissolved in THF (20 ml) and cooled to -78° C. under argon. N,N,N',N'-Tetramethylethylene diamine was added followed by dropwise addition of n-BuLi (3.4 ml of a 2.2M solution in hexanes) over 10 mins. After stirring at -78° C. for 1 hr, a solution of 3-methoxy-2-cyclopentene-1-one (605 mg) in THF (5 ml) was added slowly. The reaction mixture was stirred at -78° C. for 1 hr before warming to 0° C. 1 M HCl (20 ml) was added, and after 10 min the mixture was extracted with ethyl acetate (2*50 ml). The combined organic phases were washed with brine (30 ml), dried over magnesium sulfate, and concentrated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as yellow oil (128 mg, 13%); m/z (ES+) 279 (M+1)+.

Reference： [1]Current Patent Assignee: PFIZER INC - US2002/161041, 2002, A1 Current Patent Assignee: PFIZER INC - US6828460, 2004, B2

44
[ 4683-50-5 ]
3-(4-methyl-3-pentenyl)-2-cyclopenten-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 1-bromo-4-methylpent-3-ene With magnesium In diethyl ether at 25 - 40℃; for 1h; Stage #2: 3-methoxycyclopent-2-enone In diethyl ether at 25℃; for 0.5h;	1 Preparation of 3-(4-methyl-3-pentenyl)-2-cyclopenten-1-one Magnesium turnings 2.1 g (0.086 mole) were added to 50 ml diethyl ether with stirring. 1-Bromo-4-methyl-3-pentene 10 g (0.061 mole) was added dropwise over 30 minutes. The reaction was allowed to warm from 25° C. to 40° C. during the addition and aged for 30 minutes. A solution of 3-Methoxy-2-cyclopenten-1-one, 10 g (0.089 mole) in diethyl ether was added at 25° C. The resulting mixture was aged 30 minutes then quenched with 20% aqueous acetic acid (50 ml). The organic layer was dried over sodium sulfate, filtered and distilled to give 6.6 g (65% yield) of 3-(4-methyl-3-pentenyl)-2-cyclopenten-1-one. The 3-(4-methyl-3-pentenyl)-2-cyclopenten-1-one had a boiling point (Bp) of 117° C. at 5 mmHg. NMR data: 1.62 ppm (s, 3H), 1.69 ppm (s, 3H), 2.28 ppm (q, 2H, J=7.21 Hz), 2.39-2.41 ppm (m, 2H), 2.44 ppm (t, 2H, J=7.46 Hz), 2.58 ppm (m, 2H), 5.09 ppm (t, 1H, J=6.69 Hz), 5.96 ppm (s, 1H).

Reference： [1]Current Patent Assignee: INTERNATIONAL FLAVORS & FRAGRANCES INC - US7141699, 2006, B1 Location in patent: Page/Page column 4; 5

45
[ 4683-50-5 ]
[ 82444-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	With methylamine In ethanol	10 trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(3-oxo-cyclopent-1-enyl)amino]-2H-1-benzopyran-6-carbonitrile EXAMPLE 10 trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(3-oxo-cyclopent-1-enyl)amino]-2H-1-benzopyran-6-carbonitrile 1,12 g 3-methoxy-cyclopent-2-en-1-on are reacted with 15 ml of methylamine (33% solution in ethanol) during 23 hours at 100° C. in an autoclave. Flash-chromatography (silica gel/dichloromethane, methanol 5%) on the concentrated raw material yields N-methyl-3-amino-cyclopent-2-en-1-on having a m.p. of 130°-31° C.

Reference： [1]Current Patent Assignee: Sandoz (in: Novartis); NOVARTIS AG - US5071871, 1991, A

46
[ 4683-50-5 ]
[ 49761-82-2 ]
[ 957477-28-0 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 128 - 135
[2]Chemical Communications,2007,p. 3921 - 3923

47
[ 90-14-2 ]
[ 4683-50-5 ]
[ 1026667-64-0 ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 1-Iodonaphthalene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.25h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes at -78 - -20℃; for 2h;	VI.A Example VI; Preparation of 5-(naphthalene-l -yl)bicvclo[3 1 0]hexan-2-armnes using Reaction Scheme 3A. Synthesis of 3-naphthalen-l-yl-cvclopent-2-enoneTo a stirred solution of 1-iodonapthalene (10 00 g, 39 36 mmol) in tetrahydrofuran (300 mL) at -78 0C was added «-butyllithium (2 5 M in hexanes, 17 49 mL, 43 73 mmol, 1 1 eq ) so that the reaction temperature remained < - 78 0C The reaction mixture was stirred for 15 minutes To the reaction mixture was added a solution of 3-methoxy-2-cyclopenten-l-one (5 10 g, 45 48 mmol, 1 16 eq ) in tetrahydrofuran (50 mL) so that the reaction temperature remained < -78 0C The reaction mixture was warmed to -20 0C over a 2 h peϖod and the reaction mixture was quenched with a solution of IN HCl and concentrated in vacuo to remove the organics A solution of IN HCl was added and the reaction mixture was stirred for a further 0 5 h and extracted with ethyl acetate (3 x 100 mL) The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) followed by bϖne (100 mL), dϖed over magnesium sulphate and concentrated in vacuo to afford a yellow oil The crude oil was puϖfied by flash chromatography (S1O2, ethyl acetate EPO petroleum ether 40-60, 20 % 80 %) to afford the desired compound as an off-white solid (4 01 g, 49 %) ' H NMR (400 MHz, CDCl3) δ ppm 2 68 (2H, dt, J 2, 4 8 Hz, CH2), 3 16 (2η, td, J 2 4, 4 8 Hz, CH2), 6 51 ( 1 η, t, J 1 6 Hz, CH), 7 54-7 60 (4η, m, ArH), 7 93-8 01 (2η, m, ArH), 8 10-8 18 (1 η, m, ArH)

Reference： [1]Current Patent Assignee: ETHISMOS RESEARCH INC - WO2008/57575, 2008, A2 Location in patent: Page/Page column 79-80

48
[ 624-31-7 ]
[ 4683-50-5 ]
[ 65564-87-6 ]

Yield	Reaction Conditions	Operation in experiment
63.5%	Stage #1: 4-tolyl iodide With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.25h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes at -78 - -20℃; for 2h;	II.A Example II; Preparation of 5-(4-methylphenyl)bicyclo[3 1 0]hexan-2-amines using Reaction Scheme 3A. Synthesis of 3-p-tolyl-cvclopent-2-en-l-oneA solution of 4-iodotoluene (10 g, 45 mmol) in THF (300 mL) at -78 0C was treated with a solution of n-butyllithjum (2 5 M in hexanes, 20 mL, 50 mmol) such that the reaction temperature remained < -78 0C After 15 minutes, a solution of 3- methoxy-2-cyclopenten-l-one (5 78 g, 52 mmol) in THF (50 mL) was added such that the reaction temperature remained < -780C The reaction mixture was warmed to -20 0C over 2 h, quenched with a solution of IN HCl and concentrated in vacuo to remove THF A solution of IN HCl (40 mL) was added, the solution was stirred for 30 min and extracted with EtOAc (3x) The combined organic extracts were washed with saturated aqueous NaHCO3, bnne, dϖed over MgSθ4, filtered and concentrated in vacuo The residue was puϖfied by silica gel chromatography using heptane/EtOAc as the eluting solvent to afford 4 92 g of 3-p-tolyl-cyclopent-2-enone as a white EPO powder (Yield 63 5%) 1H NMR (400 MHz, CHLOROFORM-rf) δ ppm 2 42 (s, 3 H) 2 59 (ddd, J=4 83, 2 64, 2 49 Hz, 2 H) 3 05 (td, J=4 98, 1 76 Hz, 2 H) 6 55 (t, J=I 66 Hz, 1 H) 7 27 (d, J=S 00 Hz, 2 H) 7 57 (dt, J=8 30, 1 90 Hz, 2 H)

Reference： [1]Current Patent Assignee: ETHISMOS RESEARCH INC - WO2008/57575, 2008, A2 Location in patent: Page/Page column 56-57

49
[ 580-13-2 ]
[ 4683-50-5 ]
[ 98586-03-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes at -78 - -20℃; for 2h;	VIII.A Example VlII; Preparation of 5-(naphthalene-2-yl)bicvclo[3 1 0]hexan-2-amines using Reaction Scheme 3A. Synthesis of 3-naphthalen-2-vI-cyclopent-2-enoneA solution of 2-bromonapthalene (8 03 g, 38 8 mmol) in anhydrous tetrahydrofuran (200 mL) at -78 0C was treated with a solution of «-butyllithium (1 6 M in hexane, 26 9 mL, 43 0 mmol, 1 1 eq ) such that the reaction temperature remained at -78 0C After 15 min, a solution of 3-methoxy-2-cyclopenten- l-one (5 0 g, 44 6 mmol, 1 leq ) in anhydrous tetrahydrofuran (50 mL) was added such that the reaction temperature remained below -78 0C The reaction was warmed to -20 0C EPO over 2 h, quenched with a solution of IN HCl (100 mL) and concentrated in vacuo to remove tetrahydrofuran A solution of IN HCl (100 mL) was added, stirred for 30 mm and extracted with ethylacetate (3 x 100 mL) The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (100 mL), bnne (100 mL), dϖed over magnesium sulphate, filtered and concentrated in vacuo The residue was puϖfied by silica gel chromatography using 3 7 ethyl acetate/petrol as the eluting solvent to afford (2 77 g, 28%) as a white solid 1H NMR (400 MHz, CDCl3) δ ppm 2 63-2 66 (2H, m, CH2), 3 17-3 20 (2η, m, CH2), 6 70 (1 η, t, J 1 6 Hz, CH), 7 53-7 59 (2η, m, ArH), 7 75 (1η, dd, J 1 6, 8 5 Hz, ArH), 7 85-7 93 (3η, m, ArH), 8 12 (1 η, s, ArH)

Reference： [1]Current Patent Assignee: ETHISMOS RESEARCH INC - WO2008/57575, 2008, A2 Location in patent: Page/Page column 87-88

50
[ 4683-50-5 ]
[ 20555-91-3 ]
[ 1026667-58-2 ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: 3,4-dichloroiodobenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.25h; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes at -78 - -20℃; for 2h;	IV.A Example IV; Preparation of 5-(3,4-dichlorophenyDbicvclof3 1 0]hexan-2 -amines using Reaction Scheme 3A. Synthesis of 3-(3,,4-dichlorophenyl)cvclopent-2-en-l-oneA solution of 1 , 2-dichloro-4-iodobenzene (1 0 g, 3 66 mmol) in THF (50 mL) at -780C was treated with a solution of n-butylhthium (2 5 M in hexanes, 1 5 mL, 3 8 mmol) such that the reaction temperature remained < -780C After 15 min, a solution of 3-methoxy-2-cyclopenten- l-one (0 452 g, 3 96 mmol) in THF (20 mL) was added such that the reaction temperature remained < -78°C The reaction mixture was EPO warmed to -2O0C over 2 h, quenched with a solution of IN HCl and concentrated in vacuo to remove THF A solution of IN HCl (5 mL) was added, the solution was stirred for 30 min and extracted with EtOAc (2x) The combined organic extracts were washed with saturated aqueous NaHCO3, bϖne, dried over MgSθ4, filtered and concentrated in vacuo The residue was puϖfied by silica gel chromatography using EtO Ac/Heptanes as the eluting solvent to afford 0 3 g of target compound as a white powder (Yield 36%) 1H NMR (400 MHz, CHLOROFORM-^ δ ppm 2 58 - 2 62 (m, 2 H) 2 97 - 3 03 (m, 2 H) 6 56 (t, 1 H) 7 45 - 7 55 (m, 2 H) 7 71 (d, 1 H)

Reference： [1]Current Patent Assignee: ETHISMOS RESEARCH INC - WO2008/57575, 2008, A2 Location in patent: Page/Page column 69-70

51
[ 4683-50-5 ]
[ 14203-25-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-Bromosuccinimide In dichloromethane at 25℃; for 16h;	7.B Example 7B; 2-bromo-3-methoxycyclopent-2-enone; A mixture of Example 7A (500 mg, 4.46 mmol) and Λ^-bromosuccinimide (794 mg, 4.46 mmol) in dichloromethane (5 mL) was stirred at 25 °C for 16 hours. The mixture was concentrated in vacuo. The residue was purified on a silica column (dichloromethane/methanol = 200:1, v/v) to afford the title compound (650 mg, 3.40 mmol, 76% yield) as a solid. .H NMR (400 MHz, CDC13) δ ppm 4.12 (s, 3H), 2.79-2.82 (m, 2H), 2.62-2.65 (m, 2H); LC/MS (ESI) m/z 191 (M+H)+.
69%	With N-Bromosuccinimide In 1,2-dichloro-ethane at 0℃; for 2.5h;	1.7 Λ/-Bromosuccinimide (24.92g, 0.140 mol) is added, portionwise over one hour, to a stirred solution of 3-methoxycyclopent-2-enone (14.95 g, 0.133 mol) in 1 ,2- dichloroethane (300 ml) at 0 0C in an amber flask. The reaction is stirred at 00C for a further 90 minutes and then any remaining solid is removed by filtration. The filtrate is evaporated under reduced pressure, and the residue is dissolved in warm toluene (600ml) and washed quickly with ice-cold water (2 x 100ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure until approximately 150 ml remains. The flask is cooled in an ice bath and left for 30 minutes. The resultant precipitate is removed by filtration, washed with hexane (50 ml) and dried to give 2-bromo-3-methoxycyclopent-2-enone (17.5g, 69%)
	With N-Bromosuccinimide In 1,2-dichloro-ethane at 0℃; for 2.5h;	2.1 Step 1 : Preparation of 2-bromo-3-methoxycyclopent-2-enone.; /V-Bromosuccinimide (24.92 g, 0.140 mol) is added, portionwise, over 1 hour to a stirred solution of 3-methoxycyclopent-2-enone (14.95 g, 0.133 mol) in 1 ,2-dichloroethane (300 ml) at 00C in an amber flask. The reaction mixture is stirred at O0C for a further 90 minutes and then any remaining solid is removed by filtration. The filtrate is evaporated to dryness under reduced pressure, the resultant solid is dissolved in warm toluene (600 ml) and washed quickly with ice- cold water (2 x 100 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure until approximately 150 ml remains. The residue is cooled with an ice bath and left for 30 minutes. The resultant solid is removed by filtration, washed with hexane (50 ml) and air-dried to give 2-bromo-3-methoxycyclopent-2- enone.

	With N-Bromosuccinimide In 1,2-dichloro-ethane at 0℃; for 2.5h;	1.1 Step 1 :Preparation of 2-bromo-3-methoxy-cvclopent-2-enoneTo a stirred solution of 3-methoxy-cyclopent-2-enone (14.95g, 0.133 mmol) in 1 ,2-dichloroethane (300ml) at 00C in an amber flask is added portionwise over one hour Λ/-bromosuccinimide (24.92g, 140 mmol). The reaction is stirred at 0 0C for a further 90 minutes and then any remaining solid isremoved by filtration. The filtrate isevaporated to dryness under reduced pressure, the resultant solid dissolved in warm toluene (600ml) and washed quickly with water (2 x 100ml). The organic phase isevaporated under reduced pressure until a precipitate appears. The residue is cooled overnight in a fridge. The resultant solid isremoved by filtration, washed with hexane (50ml) and air-dried to give 15.2 g of 2-bromo-3-methoxy-cyclopent-2-enone as a white crystalline solid.
	With N-Bromosuccinimide In 1,2-dichloro-ethane at 0℃; for 2.5h;	Step 1: Preparation of 2-bromo-3-methoxy-cyclopent-2-en- 1-one. N-Bromosuccinimide (24.92 g, 0.140 mol) is added, portionwise, over 1 hour to a stirred solution of 3-methoxycyclopent-2-enone (14.95 g, 0.133 mol) in I ,2-dichloroethane (300 ml) at 0°C in an amber flask. The reaction mixture is stirred at 0°C for a further 90 minutes and then any remaining solid is removed by filtration. The filtrate is evaporated to dryness under reduced pressure, the resultant solid is dissolved in warm toluene (600 ml) and washed quickly with ice- cold water (2 x 100 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure until approximately 150 ml remains. The residue is cooled with an ice bath and left for 30 minutes. The resultant solid is removed by filtration, washed with hexane (50 ml) and air-dried to give 2-bromo-3-methoxy-cyclopent-2-en-1- one.

Reference： [1]Current Patent Assignee: ABBVIE INC; ABBOTT LABORATORIES INC - WO2012/83170, 2012, A1 Location in patent: Page/Page column 181
[2]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2010/81894, 2010, A1 Location in patent: Page/Page column 48
[3]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2009/19005, 2009, A2 Location in patent: Page/Page column 54
[4]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2010/69834, 2010, A1 Location in patent: Page/Page column 55
[5]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2014/195327, 2014, A1 Location in patent: Page/Page column 109

52
[ 3859-41-4 ]
[ 77-78-1 ]
[ 4683-50-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In acetone at 20 - 60℃; for 8h;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

53
[ 7766-51-0 ]
[ 4683-50-5 ]
[ 1118944-98-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at -78℃; Inert atmosphere; Stage #2: 4-iodobut-1-ene In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at -78 - 0℃; for 3h; Inert atmosphere;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

54
[ 4683-50-5 ]
[ 611-17-6 ]
[ 1118944-94-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: 1-bromomethyl-2-chlorobenzene In tetrahydrofuran; hexane at -78℃; Inert atmosphere;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

55
[ 4683-50-5 ]
[ 106-95-6 ]
[ 1118944-96-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78℃; Inert atmosphere;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

56
[ 4683-50-5 ]
[ 623-49-4 ]
[ 1118945-12-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: 3-methoxycyclopent-2-enone With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78℃; Stage #2: ethyl cyanoformate In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; toluene at -78℃; for 1.25h; Stage #3: ethyl cyanoformate Further stages;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

57
[ 4683-50-5 ]
[ 623-49-4 ]
[ 1118945-02-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: ethyl cyanoformate In tetrahydrofuran; hexane at -78℃; Inert atmosphere;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

58
[ 4683-50-5 ]
[ 3188-13-4 ]
[ 1118945-00-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at -78℃; Inert atmosphere; Stage #2: ethyl chloromethyl ether In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane at -78 - 0℃; for 3h; Inert atmosphere;

Reference： [1]Schule, Arnaud; Liang, Huan; Vors, Jean-Pierre; Ciufolini, Marco A. [Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1587 - 1597]

59
[ 4683-50-5 ]
[ 66222-28-4 ]
[ 119090-37-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: (benzyloxymethyl)tributylstannane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexane at -78 - 20℃; for 5.16667h; Inert atmosphere;

Reference： [1]Wang, Jingxin; Lee, Vincent; Sintim, Herman O. [Chemistry - A European Journal, 2009, vol. 15, # 12, p. 2747 - 2750]

60
[ 4683-50-5 ]
(E)-1-iodo-5-methylhex-3-ene [ No CAS ]
[ 1245503-58-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: (E)-1-iodo-5-methylhex-3-ene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes; diethyl ether at -78 - -30℃; for 2.5h; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; hexanes; diethyl ether; water

Reference： [1]Wencel-Delord, Joanna; Alexakis, Alexandre; Crevisy, Christophe; Mauduit, Marc [Organic Letters, 2010, vol. 12, # 19, p. 4335 - 4337]

61
[ 4683-50-5 ]
[ 2622-05-1 ]
[ 61765-58-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 3-methoxycyclopent-2-enone; allylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran; water Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 1h; Inert atmosphere;

Reference： [1]Wencel-Delord, Joanna; Alexakis, Alexandre; Crevisy, Christophe; Mauduit, Marc [Organic Letters, 2010, vol. 12, # 19, p. 4335 - 4337]

62
[ 4683-50-5 ]
[ 119245-02-2 ]
[ 149191-26-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: (E)-3-hexenyl iodide With n-butyllithium In hexanes; diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes; diethyl ether at -78 - -30℃; for 3h; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; hexanes; diethyl ether; water

Reference： [1]Wencel-Delord, Joanna; Alexakis, Alexandre; Crevisy, Christophe; Mauduit, Marc [Organic Letters, 2010, vol. 12, # 19, p. 4335 - 4337]

63
[ 4683-50-5 ]
[ 108330-00-3 ]
[ 1245503-59-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: (E)-4-<(tert-butyldimethylsilyl)oxy>-1-iodo-1-butene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran; hexanes; diethyl ether at -78 - -30℃; for 3h; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; hexanes; diethyl ether; water

Reference： [1]Wencel-Delord, Joanna; Alexakis, Alexandre; Crevisy, Christophe; Mauduit, Marc [Organic Letters, 2010, vol. 12, # 19, p. 4335 - 4337]

64
[ 50675-18-8 ]
[ 4683-50-5 ]
[ 1262512-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methoxycyclopent-2-enone With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; for 18.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; n-heptane; ethylbenzene	1 A solution of S-methoxy-cyclopent^-enone (18.8 g, 0.17 mol) in THF (200 ml) was added drop wise over 30 minutes (using an addition funnel) to a solution of lithium diisopropylamide solution (1.8 M in tetrahydrofuran/heptane/ethylbenzene, 103 ml, 0.18 mol) in THF (150 ml) at -78 0C, under nitrogen and allowed to stir at this temperature for 30 minutes. Tetrahydropyranyl-4-carbaldehyde (21 g, 0.18 mol) was then added drop wise and the reaction stirred at -78 0C for 30 minutes, before being allowed to warm to room temperature overnight (18 h). The reaction was then quenched by the addition of 1 M hydrochloric acid (500 ml) and extracted with ethyl acetate (3 x 500 ml). The aqueous layer was then saturated with sodium chloride and extracted with ethyl acetate (2 x 250 ml). The combined organics were evaporated and the crude product was purified using column chromatography (EtOAc: hexane, 3:7 to 100% EtOAc) to give 5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3- methoxy-cyclopent-2-enone (20.8 g).

Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2011/12862, 2011, A1 Location in patent: Page/Page column 94; 95

65
[ 4683-50-5 ]
[ 1312768-00-5 ]
[ 1354552-41-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - -40℃;

Reference： [1]Location in patent: scheme or table Moustafa, Gamal A. I.; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko [Journal of Organic Chemistry, 2012, vol. 77, # 2, p. 1202 - 1207]

66
[ 4683-50-5 ]
[ 1373128-36-9 ]
[ 1373128-41-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 3-methoxycyclopent-2-enone; [4-(1,3-dioxolan-2-yl)butyl]magnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 5h;	General Procedure for Preparation of Enone-aldehydes. General procedure: To a stirred solution of Grignard reagent (2.5 mmol) in THF (5 mL) was added 3-alkoxyenone (2.1 mmol) at room temperature. The mixture was stirred at room temperature for another 5 h and then quenched with 10% aqueous HCl (5 mL) at 0 oC and stirred at room temperature for 5 h. The aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica-gel chromatography with EtOAc/hexanes as the eluent to furnish the enone-aldehyde.
68%	Stage #1: 3-methoxycyclopent-2-enone; [4-(1,3-dioxolan-2-yl)butyl]magnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; Inert atmosphere;

Reference： [1]Hsu, Day-Shin; Hsu, Chi-Wei [Tetrahedron Letters, 2012, vol. 53, # 17, p. 2185 - 2188]
[2]Hsu, Day-Shin; Chen, Chih-Hao; Hsu, Chi-Wei [European Journal of Organic Chemistry, 2016, vol. 2016, # 3, p. 589 - 598]

67
[ 4683-50-5 ]
[ 91083-05-5 ]
[ 109390-76-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 3-methoxycyclopent-2-enone; (3-(1,3-dioxolan-2-yl)propyl)magnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 5h;	General Procedure for Preparation of Enone-aldehydes. General procedure: To a stirred solution of Grignard reagent (2.5 mmol) in THF (5 mL) was added 3-alkoxyenone (2.1 mmol) at room temperature. The mixture was stirred at room temperature for another 5 h and then quenched with 10% aqueous HCl (5 mL) at 0 oC and stirred at room temperature for 5 h. The aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica-gel chromatography with EtOAc/hexanes as the eluent to furnish the enone-aldehyde.
65%	Stage #1: 3-methoxycyclopent-2-enone; (3-(1,3-dioxolan-2-yl)propyl)magnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; Inert atmosphere;

Reference： [1]Hsu, Day-Shin; Hsu, Chi-Wei [Tetrahedron Letters, 2012, vol. 53, # 17, p. 2185 - 2188]
[2]Hsu, Day-Shin; Chen, Chih-Hao; Hsu, Chi-Wei [European Journal of Organic Chemistry, 2016, vol. 2016, # 3, p. 589 - 598]

68
[ 4683-50-5 ]
[ 1407512-39-3 ]
[ 1407512-42-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Baidya, Mahiuddin; Griffin, Kimberly A.; Yamamoto, Hisashi [Journal of the American Chemical Society, 2012, vol. 134, # 45, p. 18566 - 18569]

69
[ 4683-50-5 ]
3-methoxycyclopent-2-ene-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With ammonium cerium (IV) nitrate; iodine In acetonitrile at 24℃; for 1h; Inert atmosphere;

Reference： [1]Calandra, Nicholas A.; King, Sandra M.; Herzon, Seth B. [Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10031 - 10057]

70
[ 4683-50-5 ]
[ 1068-55-9 ]
[ 1619-28-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	In tetrahydrofuran; diethyl ether at 0 - 23℃; for 6h; Inert atmosphere;

Reference： [1]Kats-Kagan, Roman; Herzon, Seth B. [Organic Letters, 2015, vol. 17, # 8, p. 2030 - 2033]

71
[ 4683-50-5 ]
[ 37610-80-3 ]
3-(3-oxocyclopent-1-enyl)propanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: 3-methoxycyclopent-2-enone; 1,3-dioxolan-2-ylethylmagnesium bromide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; Inert atmosphere;

Reference： [1]Hsu, Day-Shin; Chen, Chih-Hao; Hsu, Chi-Wei [European Journal of Organic Chemistry, 2016, vol. 2016, # 3, p. 589 - 598]

72
[ 639863-88-0 ]
[ 4683-50-5 ]
3-(3-oxocyclopent-1-en-1-yl)butanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 1-(1,3-dioxan-2-yl)-2-bromopropane With iodine; magnesium In tetrahydrofuran at 80℃; for 1h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran at 0 - 25℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 23℃; for 7h; Ionic liquid;

Reference： [1]Liu, Xin; Liu, Junyang; Zhao, Jing; Li, Shaoping; Li, Chuang-Chuang [Organic Letters, 2017, vol. 19, # 10, p. 2742 - 2745]

73
[ 4683-50-5 ]
[ 1066-54-2 ]
3-(trimethylsilylethynyl)-2-cyclopenten-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone at 0℃; for 2h;

Reference： [1]Hsu, Day-Shin; Liou, Chang-Yan [Organic and Biomolecular Chemistry, 2018, vol. 16, # 27, p. 4990 - 4995]

74
[ 4683-50-5 ]
[ 66927-74-0 ]
[ 154616-08-7 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: 5-bromo-1-(trimethylsilyl)pentyne With iodine; magnesium In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Stage #2: 3-methoxycyclopent-2-enone In tetrahydrofuran at 0 - 23℃; for 10.5h; Inert atmosphere;

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

75
[ 4683-50-5 ]
C₁₃H₂₀O₃ [ No CAS ]
C₁₃H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C
	Multi-step reaction with 6 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

76
[ 4683-50-5 ]
C₁₄H₂₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox
	Multi-step reaction with 7 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

77
[ 4683-50-5 ]
C₁₃H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox 8.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
	Multi-step reaction with 8 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox 8.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

78
[ 4683-50-5 ]
C₁₃H₂₀O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox 8.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere
	Multi-step reaction with 9 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere 6.1: hydrogen; Crabtree's catalyst / dichloromethane / 23 °C 7.1: potassium <i>tert</i>-butylate / toluene / 1 h / 110 °C / Inert atmosphere; Glovebox 7.2: 12 h / 110 °C / Inert atmosphere; Glovebox 8.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

79
[ 4683-50-5 ]
C₁₄H₂₄OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness
	Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

80
[ 4683-50-5 ]
C₁₁H₁₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

81
[ 4683-50-5 ]
C₁₇H₂₀O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere 4.1: bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 23 °C / Inert atmosphere 4.1: bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

82
[ 4683-50-5 ]
C₁₃H₁₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

83
[ 4683-50-5 ]
C₁₃H₁₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: magnesium; iodine / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere 1.2: 10.5 h / 0 - 23 °C / Inert atmosphere 2.1: C₅₀H₅₀Ag₂N₄O₆S₂; copper(II) bis(trifluoromethanesulfonate) / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 °C / Inert atmosphere; Darkness 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / Inert atmosphere; Cooling 3.2: 3 h / -78 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 23 °C / Inert atmosphere 5.1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate / dichloromethane / 4 h / 23 °C / Inert atmosphere

Reference： [1]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]
[2]Arya, Piyush; Peng, Cheng; Snyder, Scott A.; Zhou, Zhiyao [Angewandte Chemie - International Edition, 2020, vol. 59, # 32, p. 13521 - 13525][Angew. Chem., 2020, vol. 132, # 32, p. 13623 - 13627,5]

84
[ 4683-50-5 ]
C₁₈H₂₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: dichloromethane / 360 h / 25 °C / UV-irradiation; Inert atmosphere
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: dichloromethane / 360 h / 25 °C / UV-irradiation; Inert atmosphere

Reference： [1]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[2]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]

85
[ 4683-50-5 ]
C₁₈H₂₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: Crabtree's catalyst; hydrogen / dichloromethane / 5 h / 25 °C / 750.08 Torr
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: Crabtree's catalyst; hydrogen / dichloromethane / 5 h / 25 °C / 750.08 Torr

Reference： [1]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[2]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]

86
[ 4683-50-5 ]
C₁₈H₂₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr

Reference： [1]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[2]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]

87
[ 4683-50-5 ]
C₁₉H₂₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: C₃₈H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen / toluene / 10 h / 35 °C / 18751.9 Torr 3.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / -45 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr 3.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / -45 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: C₃₈H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen / toluene / 10 h / 35 °C / 18751.9 Torr 4.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 4.2: 1 h / -45 °C / Inert atmosphere

Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr 4.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 4.2: 1 h / -45 °C / Inert atmosphere

Reference： [1]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[2]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[3]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[4]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]

88
[ 4683-50-5 ]
C₁₉H₂₂O₃ [ No CAS ]
C₁₉H₂₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: C₃₈H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen / toluene / 10 h / 35 °C / 18751.9 Torr 3.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / -45 °C / Inert atmosphere 4.1: bis-[(trifluoroacetoxy)iodo]benzene; sodium carbonate / 0.5 h / 25 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr 3.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / -45 °C / Inert atmosphere 4.1: bis-[(trifluoroacetoxy)iodo]benzene; sodium carbonate / 0.5 h / 25 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: (aS)-Ir/In-BiphPHOX; hydrogen / 1,2-dichloro-ethane / 10 h / 35 °C / 11251.1 Torr 4.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 4.2: 1 h / -45 °C / Inert atmosphere 5.1: bis-[(trifluoroacetoxy)iodo]benzene; sodium carbonate / 0.5 h / 25 °C / Inert atmosphere

Multi-step reaction with 5 steps 1.1: lithium diisopropyl amide / toluene / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; thionyl chloride / toluene / 1 h / 55 °C / Inert atmosphere 3.1: C₃₈H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen / toluene / 10 h / 35 °C / 18751.9 Torr 4.1: tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 4.2: 1 h / -45 °C / Inert atmosphere 5.1: bis-[(trifluoroacetoxy)iodo]benzene; sodium carbonate / 0.5 h / 25 °C / Inert atmosphere

Reference： [1]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[2]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[3]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]
[4]Chen, Ruyi; Ding, Hanfeng; Hu, Jialei; Xie, Hujun; Xiong, Fengping; Zhao, Yifan [Journal of the American Chemical Society, 2022, vol. 144, # 6, p. 2495 - 2500]

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CAS No. :	4683-50-5	MDL No. :	MFCD00192267
Formula :	C₆H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DTWCFCILAJVNPE-UHFFFAOYSA-N
M.W :	112.13	Pubchem ID :	643476
Synonyms :

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.65
TPSA :	26.3 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) :	-6.82 cm/s

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	0.23
Log Po/w (WLOGP) :	0.88
Log Po/w (MLOGP) :	-0.04
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	0.79

[ CAS No. 4683-50-5 ] {[proInfo.proName]}

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[ 4683-50-5 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Log S (ESOL) :	-0.61
Solubility :	27.3 mg/ml ; 0.243 mol/l
Class :	Very soluble
Log S (Ali) :	-0.34
Solubility :	51.0 mg/ml ; 0.455 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.97
Solubility :	11.9 mg/ml ; 0.106 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
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.
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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.
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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.
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P332	IF SKIN irritation occurs:
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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

[ CAS No. 4683-50-5 ] {[proInfo.proName]}

Quality Control of [ 4683-50-5 ]

Related Doc. of [ 4683-50-5 ]

Product Details of [ 4683-50-5 ]

Calculated chemistry of [ 4683-50-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4683-50-5 ]

Application In Synthesis of [ 4683-50-5 ]

[ 4683-50-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 4683-50-5 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Ethers

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 4683-50-5 ]