methyl (3E,2R)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)pent-3-enoate | 145090-64-8

• 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: methyl (3E,2R)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)pent-3-enoate
• CAS: 145090-64-8
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: LZFJSBHGTCZIIX-MYSGNRETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (3E,2R)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)pent-3-enoate 在 甲酸 、 双氧水 、 臭氧 作用下， 生成 methyl hydrogen (S)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)malonate
  参考文献：
  名称：

  1-(N,N-Diisopropylcarbamoyloxy)-1,3-dimethylallyllithium·(−)-sparteine: stereochemistry of the enantioselective carboxylation and methoxycarbonylation

  摘要：

  The title compound (S)-3/(-)-2, easily available through deprotonation of the racemic O-(2-alkenyl) carbamate under kinetic resolution, undergoes with carbon dioxide or methyl chloroformate predominantly a-substitution with stereoinversion. The absolute configuration of the formed methyl carboxylate is established by chemical correlation, thus correcting our former suggestion3a.

  DOI：

  10.1016/s0040-4020(01)86587-x
• 作为产物：
  描述：

  、 氯甲酸甲酯 反应 0.08h， 生成 methyl (3E/Z)-4-methyl-4-(N,N-diisopropylcarbamoyloxy-2-methyl)but-3-enoate 、 methyl (3E,2S)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)pent-3-enoate 、 methyl (3E,2R)-2-methyl-2-(N,N-diisopropylcarbamoyloxy)pent-3-enoate
  参考文献：
  名称：

  1-(N,N-Diisopropylcarbamoyloxy)-1,3-dimethylallyllithium·(−)-sparteine: stereochemistry of the enantioselective carboxylation and methoxycarbonylation

  摘要：

  The title compound (S)-3/(-)-2, easily available through deprotonation of the racemic O-(2-alkenyl) carbamate under kinetic resolution, undergoes with carbon dioxide or methyl chloroformate predominantly a-substitution with stereoinversion. The absolute configuration of the formed methyl carboxylate is established by chemical correlation, thus correcting our former suggestion3a.

  DOI：

  10.1016/s0040-4020(01)86587-x