2-isopropyl-5-methylcyclohexa-1,5-dien-1-yl 2-chloroacetate | 1415503-66-0

• 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-isopropyl-5-methylcyclohexa-1,5-dien-1-yl 2-chloroacetate
• 英文别名: (5-Methyl-2-propan-2-ylcyclohexa-1,5-dien-1-yl) 2-chloroacetate；(5-methyl-2-propan-2-ylcyclohexa-1,5-dien-1-yl) 2-chloroacetate
• CAS: 1415503-66-0
• 化学式: C₁₂H₁₇ClO₂
• 分子量: 228.719
• InChiKey: YWHXJZBXWFPMQL-UHFFFAOYSA-N

物化性质

• 沸点：
  310.9±41.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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-isopropyl-5-methylcyclohexa-1,5-dien-1-yl 2-chloroacetate 在 N-9-anthracenylmethylcinchonidinium chloride 、 potassium hydroxide 、 2-氯乙醇 作用下， 以 氯仿 、 均三甲苯 为溶剂， 反应 24.0h， 以99%的产率得到(-)-胡椒酮
  参考文献：
  名称：

  Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts

  摘要：

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

  DOI：

  10.1021/ol3027363
• 作为产物：
  描述：

  胡椒酮 、 氯乙酸酐 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 正己烷 为溶剂， 反应 1.5h， 以58%的产率得到2-isopropyl-5-methylcyclohexa-1,5-dien-1-yl 2-chloroacetate
  参考文献：
  名称：

  Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts

  摘要：

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

  DOI：

  10.1021/ol3027363

文献信息

• Hydrolytic Enantioselective Protonation of Cyclic Dienyl Esters and a β-Diketone with Chiral Phase-Transfer Catalysts
  作者：Eiji Yamamoto、Daichi Gokuden、Ayano Nagai、Takashi Kamachi、Kazunari Yoshizawa、Akiyuki Hamasaki、Tamao Ishida、Makoto Tokunaga

  DOI：10.1021/ol3027363

  日期：2012.12.21

  Hydrolytic enantioselective protonation of dienyl esters and a beta-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active alpha,beta-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).