2-丙烯酸,3-[1-(2-溴乙基)环己基]-,乙基酯,(E)- | 139376-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-丙烯酸,3-[1-(2-溴乙基)环己基]-,乙基酯,(E)-
• 英文名称: ethyl (E)-3-<1-(2-bromoethyl)cyclohexyl>propenoate
• 英文别名: ethyl (E)-3-[1-(2-bromoethyl)cyclohexyl]prop-2-enoate
• CAS: 139376-70-8
• 化学式: C₁₃H₂₁BrO₂
• 分子量: 289.213
• InChiKey: GHRNRMXGHPYMEZ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  2-丙烯酸,3-[1-(2-溴乙基)环己基]-,乙基酯,(E)- 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以95%的产率得到ethyl (E)-3-<1-(2-iodoethyl)cyclohexyl>propenoate
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025
• 作为产物：
  描述：

  1-(2-bromoethyl)-1-ethenylcyclohexane 在 二甲基硫 、 臭氧 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 2-丙烯酸,3-[1-(2-溴乙基)环己基]-,乙基酯,(E)-
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025