ethyl (4-iso-propylcyclohexylidene)acetate | 725707-39-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (4-iso-propylcyclohexylidene)acetate
• CAS: 725707-39-1
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: AEINRORMNMXYNL-LUAWRHEFSA-N

物化性质

• 沸点：
  278.5±9.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (4-iso-propylcyclohexylidene)acetate 在 Ra-Ni 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 35.0~70.0 ℃ 、275.79 kPa 条件下， 反应 36.0h， 生成
  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
• 作为产物：
  描述：

  4-异丙基环己酮 、 乙氧甲酰基亚甲基三苯基膦 以 乙腈 为溶剂， 反应 0.33h， 以99%的产率得到ethyl (4-iso-propylcyclohexylidene)acetate
  参考文献：
  名称：

  微波辅助的区域化单环和二酮与稳定的磷内酯的区域选择性烯化

  摘要：

  在控制的微波加热下，许多环状的单酮和二酮与（carbethoxyethidene）三苯基磷芳烷进行区域选择性烯烃化反应。4-取代的环己酮或1,2-和1,4-环己二酮与ylide在MeCN中在190°C下进行Wittig反应20分钟，得到的外环烯烃的异构体比率> 94：6。另一方面，在20mol％DBU的存在下在230℃下进行20分钟的相同反应提供了＞ 83:17异构体比率的内环烯烃。碱介导的环外烯烃异构化成环内异构体主要是由产物的热力学稳定性驱动的，并且研​​究了环结构对去共轭作用的影响。

  DOI：

  10.1016/j.tet.2005.12.060

文献信息

• Highly regioselective Wittig reactions of cyclic ketones with a stabilized phosphorus ylide under controlled microwave heating
  作者：Jinlong Wu、Huafeng Wu、Shaoyong Wei、Wei-Min Dai

  DOI：10.1016/j.tetlet.2004.03.198

  日期：2004.5

  Significant base and temperature effects on the Wittig reactions of cyclohexanones with (carbethoxymethylene)triphenylphosphorane under microwave irradiation were observed. For the Wittig reactions carried out in a domestic microwave oven under solvent-free conditions, the initially formed exo-olefin products isomerized into the thermodynamically more stable endo-olefins due to uncontrolled high reaction temperature. In sharp contrast, under controlled microwave heating, both exo- and endo-olefins have been selectively synthesized by accurately regulating the reaction temperature with or without a base. (C) 2004 Elsevier Ltd. All rights reserved.