1ref-Hydroxy-2cis-methyl-2trans-ethoxycarbonyl-cyclohexan | 173006-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1ref-Hydroxy-2cis-methyl-2trans-ethoxycarbonyl-cyclohexan
• 英文别名: ethyl (1R,2R)-2-hydroxy-1-methylcyclohexane-1-carboxylate
• CAS: 173006-70-7
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JWQZGIYBARNRDS-PSASIEDQSA-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-2cis-methyl-2trans-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

文献信息

• Cycloalkylamines as monoamine reuptake inhibitors
  申请人：Shao Liming

  公开号：US20070203111A1

  公开（公告）日：2007-08-30

  The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.

  本发明涉及新型环己胺衍生物及其在中枢神经系统（CNS）疾病的治疗和/或预防中的应用，例如抑郁症、焦虑症、精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及包含本发明化合物的制药组合物，以及抑制内源性单胺，如多巴胺、5-羟色胺和去甲肾上腺素从突触间隙中再摄取的方法和调节一个或多个单胺转运体的方法。
• CYCLOALKYLAMINES AS MONOAMINE REUPTAKE INHIBITORS
  申请人：Shao Liming

  公开号：US20100190861A1

  公开（公告）日：2010-07-29

  The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.

  本发明涉及新型环己基胺衍生物及其在治疗和/或预防中枢神经系统（CNS）疾病方面的应用，例如抑郁症，焦虑症，精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及含有本发明化合物的制药组合物，以及抑制内源性单胺，如多巴胺，5-羟色胺和去甲肾上腺素从突触间隙中再摄取的方法，以及调节一个或多个单胺转运体的方法。
• US8877975B2
  申请人：——

  公开号：US8877975B2

  公开（公告）日：2014-11-04