2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid | 1408287-41-1

• 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: 2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid
• 英文别名: 2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yl]oxycarbonylbenzoic acid
• CAS: 1408287-41-1
• 化学式: C₁₈H₂₁ClO₄
• 分子量: 336.815
• InChiKey: YJDJGEKWFIPORN-CQSZACIVSA-N

物化性质

• 沸点：
  490.6±45.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid 在 potassium tert-butylate 、 叔丁醇 作用下， 反应 1.0h， 以55%的产率得到2-甲基-6-次甲基-2,7-辛二烯-4-醇
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family

  摘要：

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.

  DOI：

  10.1134/s1070428012090035
• 作为产物：
  描述：

  2-[8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid 在 硫酸 、 水 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 2-[(4S)-8-chloro-2-methyl-6-methylideneoct-2-en-4-yloxycarbonyl]benzoic acid
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family

  摘要：

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.

  DOI：

  10.1134/s1070428012090035

文献信息

• Improved synthesis of optically active ipsdienol
  作者：V. N. Kovalenko、K. N. Prokhorevich

  DOI：10.1134/s1070428016050250

  日期：2016.5

  of monoterpene alcohol ipsdienol 1, an actual pheromone component of bark beetle of genus Ips. The key synthesis stage was the resolution of the direct precursor of the ipsdienol, (±)-6-methyl-2-(2chloroethyl)hepta-1,5-dien-4-ol by its conversion into acid phthalate and the crystallization of the acid phthalate as salt with (+)or (–)-1-phenylethylamine. Then the optically active acid phthalates (S)-2

  在我们之前的出版物 [1] 中，描述了用于制备单萜醇异丙二烯醇 1 的两种对映异构体的简单程序，异丙双烯醇 1 是 Ips 属树皮甲虫的实际信息素成分。关键合成阶段是异丙二烯醇的直接前体 (±)-6-methyl-2-(2chloroethyl)hepta-1,5-dien-4-ol 通过转化为邻苯二甲酸和结晶邻苯二甲酸与 (+) 或 (-)-1-苯乙胺的盐。然后用叔丁醇钾在叔丁醇中处理光学活性酸邻苯二甲酸酯(S)-2和(R)2。通过在一个阶段中酯部分的脱氯化氢和同时醇解以55%的产率获得(S)或(R)-异丙二烯醇。