ethyl (1S,3R)-(-)-3-methyl-1-(nitromethyl)cyclohexaneacetate | 221157-80-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1S,3R)-(-)-3-methyl-1-(nitromethyl)cyclohexaneacetate
• 英文别名: ethyl 2-[(1S,3R)-3-methyl-1-(nitromethyl)cyclohexyl]acetate
• CAS: 221157-80-8
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: XRJVTOXCEXPYEJ-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,3R)-(-)-3-methyl-1-(nitromethyl)cyclohexaneacetate 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (1S,3R)-(-)-1-carboxy-3-methylcyclohexaneacetic acid
  参考文献：
  名称：

  Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom

  摘要：

  Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic beta,beta-dialkyl-gamma-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active gamma-nitroesters gave access to optically active beta,beta-disubstituted gamma-aminoacids as well as alpha,alpha-disubstituted succinic acids, both being biologically relevant compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.010
• 作为产物：
  描述：

  (R)-(+)-3-甲基环己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.75h， 生成 ethyl (1S,3R)-(-)-3-methyl-1-(nitromethyl)cyclohexaneacetate
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n

文献信息

• An in vitro investigation into conformational aspects of gabapentin
  作者：Justin S. Bryans、David C. Horwell、Giles S. Ratcliffe、Jean-Marie Receveur、J.Ronald Rubin

  DOI：10.1016/s0968-0896(99)00023-1

  日期：1999.5

  Conformational analysis of constrained cyclohexane systems was pioneered fifty years ago by Barton and Hassel. We now report an investigation based on a conformational analysis of a number of novel cyclohexane based Gabapentin analogues coupled with their in vitro evaluation at the Gabapentin binding site. These data are used to propose a possible binding conformation for Gabapentin. (C) 1999 Elsevier Science Ltd. All rights reserved.