methyl (S)-1-methyl-2-oxocyclohexanecarboxylate | 89656-83-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-1-methyl-2-oxocyclohexanecarboxylate
• 英文别名: Methyl (S)-1-methyl-2-oxocyclohexane-1-carboxylate；methyl (1S)-1-methyl-2-oxocyclohexane-1-carboxylate
• CAS: 89656-83-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: XVOWMIBAOJEFIT-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-1-methyl-2-oxocyclohexanecarboxylate 、 N-苯基双(三氟甲烷磺酰)亚胺 、 lithium diisopropyl amide 生成 methyl (1S)-1-methyl-2-(trifluoromethylsulfonyloxy)cyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  HAIZA, MOHAMMED;LEE, JUNNING;SNYDER, JOHN K., J. ORG. CHEM., 55,(1990) N7, C. 5008-5013

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-Acetyl-2-methyl-5-oxo-pentanoic acid methyl ester 在 palladium on activated charcoal 四氢吡咯 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 methyl (S)-1-methyl-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  Maiti; Ghoshal; Mukhopadhyay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1072 - 1080

  摘要：

  DOI：

文献信息

• Asymmetric alkylation of .alpha.-alkyl .beta.-keto esters
  作者：Kiyoshi Tomioka、Kaori Ando、Yutaka Takemasa、Kenji Koga

  DOI：10.1021/ja00321a050

  日期：1984.5

  Diastereoselective alkylation de lithio enamines obtenues a partir d'α-alkyl β-cetoesters et du (S)-valinate de t-butyle

  非对映选择性烷基化脱硫烯胺减少部分 d'α-烷基 β-cetoesters et du (S)-valinate de t-butyle
• Factors controlling the diastereoface selectivity in the complementary asymmetric alkylation of α-alkyl β-keto esters
  作者：Kiyoshi Tomioka、Kaori Ando、Yutaka Takemasa、Kenji Koga

  DOI：10.1016/s0040-4039(01)91410-8

  日期：1984.1

  Complementary asymmetric alkylation reaction of the lithioenamine derived from 2-methoxycarbonylcyclohexanone and (S)-valine tert-butyl ester was examined by employing the various electron pair donating additives in a toluene solvent, in order to clarify the factors controlling the diastereoface selectivity.

  为了阐明控制非对映异构体选择性的因素，通过在甲苯溶剂中使用各种给电子对添加剂，研究了衍生自2-甲氧基羰基环己酮和（S）-缬氨酸叔丁基酯的硫代亚胺的互补不对称烷基化反应。
• Stereoselective reactions. XXI. Asymmetric alkylation of α-alkyl β-keto esters to α,α-dialkyl β-keto esters having either (R)- or (S)-chiral quaternary center depending on the solvent system
  作者：Kaori Ando、Yataka Takemasa、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4020(01)80346-x

  日期：——

  Asymmetric alkylation reaction of chiral enamines prepared from alpha-alkyl beta-keto esters and (S)-valine tert-butyl ester leading to either enantiomer is described. Lithiated chiral enamines can be alkylated with alkyl halides in a toluene solvent in the presence of HMPA to give, after hydrolysis, alpha,alpha-dialkyl beta-keto esters in 70-99%ee. The reactions in the presence of THF, dioxolane, or trimethylamine. instead of HMPA, afford the corresponding antipodes with enantiomeric purities of 44-92%ee. The present method provides a procedure for the synthesis of both enantiomers of alpha,alpha-dialkyl beta-keto esters in high enantiomeric purities starting from the same chiral enamines.
• Asymmetric alkylation using chiral cyclic diols to prepare a quaternary carbon
  作者：Keisuke Kato、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0040-4020(01)87012-5

  日期：1994.3

  Asymmetric alkylation of cyclic and acyclic beta-keto ester acetals (4, 5, 13, 14, and 18) with C-2-symmetric cycloalkane-1,2-dioxy moiety proceeded in a highly diastereoselective manner to afford enol ethers (9-12, 15-17, 19a-c) with a chiral quaternary carbon.
• Kato, Keisuke; Suemune, Hiroshi; Sakai, Kiyoshi, Heterocycles, 1994, vol. 37, # 1, p. 413 - 424
  作者：Kato, Keisuke、Suemune, Hiroshi、Sakai, Kiyoshi

  DOI：——

  日期：——