ethyl (3R)-2-(3-methylcyclohexylidene)acetate | 221157-79-5

• 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: ethyl (3R)-2-(3-methylcyclohexylidene)acetate
• 英文别名: ((R)-3-methyl-cyclohexyliden-(ξ))-acetic acid ethyl ester；((R)-3-Methyl-cyclohexyliden-(ξ))-essigsaeure-aethylester；ethyl 2-[(3R)-3-methylcyclohexylidene]acetate
• CAS: 221157-79-5
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: FXLUOHJAMBWLCB-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (3R)-2-(3-methylcyclohexylidene)acetate 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (Z,3R)-(-)-(3-methylcyclohexylidene)acetaldehyde
  参考文献：
  名称：

  一种新颖且高度立体选择性的氮杂-spirocycles方法。2-epi-（+/-）-perhydrohistrionicotoxin的短总合成和2-pyrones前所未有的脱羧。

  摘要：

  [反应：见正文]描述了氮杂螺环化合物的新颖且高度立体选择性的合成。该方法的应用举例说明了在aza-spirocenter上具有高非对映异构体控制的2-epi-（+/-）-perhydrohistrionicotoxin的简短合成。在该总合成过程中观察到了2-吡喃酮环的空前脱羧。

  DOI：

  10.1021/ol020052o
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 (R)-(+)-3-甲基环己酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 ethyl (3R)-2-(3-methylcyclohexylidene)acetate
  参考文献：
  名称：

  一种新颖且高度立体选择性的氮杂-spirocycles方法。2-epi-（+/-）-perhydrohistrionicotoxin的短总合成和2-pyrones前所未有的脱羧。

  摘要：

  [反应：见正文]描述了氮杂螺环化合物的新颖且高度立体选择性的合成。该方法的应用举例说明了在aza-spirocenter上具有高非对映异构体控制的2-epi-（+/-）-perhydrohistrionicotoxin的简短合成。在该总合成过程中观察到了2-吡喃酮环的空前脱羧。

  DOI：

  10.1021/ol020052o

文献信息

• Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、Visaka U. K. Dissanayake、Giles S. Ratcliffe、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Ryszard J. Oles、John C. O'Toole、Gemma M. Perkins、Lakhbir Singh、Nirmala Suman-Chauhan、Jacqueline A. O'Neill

  DOI：10.1021/jm970649n

  日期：1998.5.1

  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.
• 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.
• A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-<i>epi</i>-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones
  作者：Michael J. McLaughlin、Richard P. Hsung、Kevin P. Cole、Juliet M. Hahn、Jiashi Wang

  DOI：10.1021/ol020052o

  日期：2002.6.1

  [reaction: see text] A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin with high diastereomeric control at the aza-spirocenter. An unprecedented decarboxylation of the 2-pyrone ring is observed in this total synthesis effort.

  [反应：见正文]描述了氮杂螺环化合物的新颖且高度立体选择性的合成。该方法的应用举例说明了在aza-spirocenter上具有高非对映异构体控制的2-epi-（+/-）-perhydrohistrionicotoxin的简短合成。在该总合成过程中观察到了2-吡喃酮环的空前脱羧。
• Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom
  作者：Fulvia Felluga、Franco Ghelfi、Giuliana Pitacco、Fabrizio Roncaglia、Ennio Valentin、Cesare Daniele Venneri

  DOI：10.1016/j.tetasy.2010.07.010

  日期：2010.9

  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.