di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl] imidodicarbonate | 944729-38-8

• 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: di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl] imidodicarbonate
• 英文别名: [(1S,2S,3S,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl] N-[[(1S,2S,3S,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]oxycarbonyl]carbamate
• CAS: 944729-38-8
• 化学式: C₂₂H₃₅NO₄
• 分子量: 377.524
• InChiKey: STFKIZNVKOTVFB-NAVXHOJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl] imidodicarbonate 在 次氯酸叔丁酯 作用下， 反应 0.5h， 生成 di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl] N-chloroimidodicarbonate
  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：

  (1S,2S,3S,5R)-(+)-异松蒎醇 在 吡啶 、 ammonium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 6.0h， 生成 di[(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl] 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