3-(2-Acetoxy-cyclohex-1-enyl)-propionic acid methyl ester | 807621-42-7

• 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: 3-(2-Acetoxy-cyclohex-1-enyl)-propionic acid methyl ester
• 英文别名: Methyl 3-(2-acetyloxycyclohexen-1-yl)propanoate
• CAS: 807621-42-7
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: OFPQPQHIXRMRTG-UHFFFAOYSA-N

物化性质

• 沸点：
  333.0±31.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-Acetoxy-cyclohex-1-enyl)-propionic acid methyl ester 在 吡啶 、 硝酸铵 、 溶剂黄146 、 三氟乙酸酐 、 锌 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(2-bromoacetyl)-1-azaspiro[4.5]decane-2,6-dione
  参考文献：
  名称：

  Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes

  摘要：

  Supply of major metabolites such as gamma-aminobutyric acid (GABA), beta-alanine and taurine is an essential instrument that shapes signalling, proper cell functioning and survival in the brain and peripheral organs. This background motivates the synthesis of novel classes of compounds regulating their selective transport through various fluid-organ barriers via the low-affinity gamma-aminobutyric acid (GABA) transporter subtype 2 (GAT2). Natural and synthetic spirocyclic compounds or therapeutics with a range of structures and biological activity are increasingly recognised in this regard. Based on pre-validated GABA transport activity, straightforward and efficient synthesis method was developed to provide an azaspiro[4.5]decane scaffold, holding a variety of charge, substituent and 3D constrain of spirocyclic amine. Investigation of the azaspiro[4.5]decane scaffold in cell lines expressing the four GABA transporter subtypes led to the discovery of a subclass of a GAT2-selective compounds with acyl-substituted azaspiro[4.5]decane core. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.100
• 作为产物：
  描述：

  乙酸异丙烯酯 、 3-(2-氧代环己基)丙酸甲酯 在 对甲苯磺酸 作用下， 反应 7.0h， 以86%的产率得到3-(2-Acetoxy-cyclohex-1-enyl)-propionic acid methyl ester
  参考文献：
  名称：

  AlMe3介导的多米诺骨牌反应可高效合成赤藓素和B-高赤藓素骨架。

  摘要：

  DOI：

  10.1002/anie.200460283