(1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl-methyl chloroformate | 944729-34-4

• 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: (1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl-methyl chloroformate
• 英文别名: [(1S,2R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl carbonochloridate
• CAS: 944729-34-4
• 化学式: C₁₁H₁₇ClO₂
• 分子量: 216.708
• InChiKey: XYFDGFZHBDTADU-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl-methyl chloroformate 在 ammonium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 di[(1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ylmethyl] imidodicarbonate
  参考文献：
  名称：

  Design and Synthesis of Chiral N-Chloroimidodicarbonates:  Application to Asymmetric Chlorination of Silyl Enol Ethers

  摘要：

  New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C-2-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the presence of a suitable Lewis acid such as Sm(OTf)(3).

  DOI：

  10.1021/jo070614n
• 作为产物：
  描述：

  三光气 、 (-)-顺式-桃金娘烷醇 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以100%的产率得到(1S,2R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl-methyl chloroformate
  参考文献：
  名称：

  Design and Synthesis of Chiral N-Chloroimidodicarbonates:  Application to Asymmetric Chlorination of Silyl Enol Ethers

  摘要：

  New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C-2-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the presence of a suitable Lewis acid such as Sm(OTf)(3).

  DOI：

  10.1021/jo070614n