(+/-)-2-octylvinyl carbonate | 173779-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (+/-)-2-octylvinyl carbonate
• 英文别名: Ethenyl octan-2-yl carbonate；ethenyl octan-2-yl carbonate
• CAS: 173779-28-7
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: VAXNKVZRGWONRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-octylvinyl carbonate 、 苯甲醇 在 4 A molecular sieve 、 immobilized lipase from Candida antarctica SP 435A 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以45%的产率得到S-(+)-benzyl-2-octyl carbonate
  参考文献：
  名称：

  Kinetic resolution of vinyl carbonates through a lipase-mediated synthesis of their carbonate and carbamate derivatives.

  摘要：

  Lipase from Candida antarctica was used in the synthesis of different chiral carbonates and carbamates through the enzymic resolution of the starting racemic vinyl carbonates. A striking feature was the changeover of the enantioselectivity with regard to the one showed when vinyl carbonates were used in the resolution of alcohols and amines, thus the S enantiomer of the vinyl carbonate was resolved whereas the same enzyme was selective towards R ones when resolving alcohols and amines. In this way, compounds obtained beforehand as R carbonates were now achieved as S ones with better e.e.'s and shorter reaction times.

  DOI：

  10.1016/s0040-4020(01)81561-1
• 作为产物：
  描述：

  仲辛醇 、 氯甲酸乙烯酯 以 吡啶 为溶剂， 反应 2.0h， 以80%的产率得到(+/-)-2-octylvinyl carbonate
  参考文献：
  名称：

  Kinetic resolution of vinyl carbonates through a lipase-mediated synthesis of their carbonate and carbamate derivatives.

  摘要：

  Lipase from Candida antarctica was used in the synthesis of different chiral carbonates and carbamates through the enzymic resolution of the starting racemic vinyl carbonates. A striking feature was the changeover of the enantioselectivity with regard to the one showed when vinyl carbonates were used in the resolution of alcohols and amines, thus the S enantiomer of the vinyl carbonate was resolved whereas the same enzyme was selective towards R ones when resolving alcohols and amines. In this way, compounds obtained beforehand as R carbonates were now achieved as S ones with better e.e.'s and shorter reaction times.

  DOI：

  10.1016/s0040-4020(01)81561-1

文献信息

• Double enantioselective enzymic synthesis of carbonates and urethanes
  作者：Marcos Pozo、Vicente Gotor

  DOI：10.1016/0957-4166(95)00369-z

  日期：1995.11

  Double enantioselective lipase-catalyzed alkoxycarbonylation of racemic alcohols and amines with racemic vinyl carbonates to yield carbonates and carbamates with two stereogenic centers was carried out using Candida antarctica lipase.