1ref-Hydroxy-2trans-methyl-2cis-ethoxycarbonyl-cyclohexan | 173006-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1ref-Hydroxy-2trans-methyl-2cis-ethoxycarbonyl-cyclohexan
• 英文别名: ethyl (1R,2S)-2-hydroxy-1-methylcyclohexane-1-carboxylate
• CAS: 173006-71-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JWQZGIYBARNRDS-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 sodium hydride 、 二乙醇胺 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1ref-Hydroxy-2trans-methyl-2cis-ethoxycarbonyl-cyclohexan
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative α-Tertiary Ketones with B-Chlorodiisopinocampheylborane

  摘要：

  Kinetic resolution of racemic alpha-tertiary ketones with 0.5-0.6 molar equiv of B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric and enantiomeric excess, with the unreacted ketone recovered in very high ee. For example, ethyl 1-methyl-8-oxocyclopentane- and -cyclohexanecarboxylates are partially reduced to recover the ketone in 91 greater than or equal to 99% ee and the product alcohols in up to 94% de, with >90% ee for the major diastereomer. Bicyclic ketones, such as 1-methyl- and 1-ethylnorcamphor, camphor, and camphenilone, are readily resolved to provide the ketone in 92 to greater than or equal to 99% ee, with the product alcohol recovered in high de and ee. Dihydrospiro[bicyclo[3.2.1]octane-2,2'(3'H)-furan]-3-one is resolved to provide the ketone in greater than or equal to 99% ee and the product alcohol in greater than or equal to 99% de. In all the cases studied, the R-isomer of the ketone is recovered when (d)Ipc(2)BCl is used for kinetic resolution, while (l)Ipc(2)BCl provides the S-ketone. Optimum conditions for obtaining the product alcohol, or the ketone, or both, in very high yields and ee have been established.

  DOI：

  10.1021/jo951206z