(1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl carbamate | 944729-35-5

• 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,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl carbamate
• 英文别名: [(1S,2S,3S,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl] carbamate
• CAS: 944729-35-5
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: BRLABJNZYDGKJF-KZVJFYERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl carbamate 在 次氯酸叔丁酯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 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 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 6.0h， 生成 (1S,2S,3S,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl carbamate
  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