(S1,R2,RS)-2-<(4-methylphenyl)sulfinyl>-1-trimethylsilyloxycyclohexanecarbonitrile | 160835-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S1,R2,RS)-2-<(4-methylphenyl)sulfinyl>-1-trimethylsilyloxycyclohexanecarbonitrile
• 英文别名: (S1,R2,RS)-2-[(4-methylphenyl)sulfinyl]-1-trimethylsilyloxycyclohexanecarbonitrile
• CAS: 160835-76-7
• 化学式: C₁₇H₂₅NO₂SSi
• 分子量: 335.543
• InChiKey: RFKFWYBDHVXILF-WWMYMODYSA-N

物化性质

• 沸点：
  462.664±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.126±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S1,R2,RS)-2-<(4-methylphenyl)sulfinyl>-1-trimethylsilyloxycyclohexanecarbonitrile 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 15.0h， 以73%的产率得到(S1,R2,RS)-1-hydroxy-2-<(4-methylphenyl)sulfinyl>cyclohexanecarbonitrile
  参考文献：
  名称：

  Highly diastereoselective Hydrocyanation of α-sulfinyl cycloalkanones

  摘要：

  Hydrocyanation of cyclic alpha-sulfinyl ketones under different conditions has been studied. The obtained results show that compounds derived from cyclohexanone react with Et(2)AlCN yielding only sulfinyl cyanohydrins exhibiting different configurations at sulfur and at hydroxylic carbon. The stereoselectivity is slightly lower but also very high starting from alpha-sulfinyl cyclopentanones. The influence of Lewis acids as well as the stereochemical course of these reactions have also been discussed.

  DOI：

  10.1016/s0040-4020(01)90484-3
• 作为产物：
  描述：

  三甲基氰硅烷 、 (S₂,R_S)-2-p-Tolylsulfinylcyclohexanone 在 potassium cyanide 、 18-crown-ether 作用下， 生成 (R1,R2,RS)-2-<(4-methylphenyl)sulfinyl>-1-trimethylsilyloxycyclohexanecarbonitrile 、 (S1,R2,RS)-2-<(4-methylphenyl)sulfinyl>-1-trimethylsilyloxycyclohexanecarbonitrile
  参考文献：
  名称：

  Highly diastereoselective Hydrocyanation of α-sulfinyl cycloalkanones

  摘要：

  Hydrocyanation of cyclic alpha-sulfinyl ketones under different conditions has been studied. The obtained results show that compounds derived from cyclohexanone react with Et(2)AlCN yielding only sulfinyl cyanohydrins exhibiting different configurations at sulfur and at hydroxylic carbon. The stereoselectivity is slightly lower but also very high starting from alpha-sulfinyl cyclopentanones. The influence of Lewis acids as well as the stereochemical course of these reactions have also been discussed.

  DOI：

  10.1016/s0040-4020(01)90484-3