<1S-trans>-(1,1-dimethylethyl)dimethyl<(5-methyl-2-methylenecyclohexyl)oxy>silane | 145668-40-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <1S-trans>-(1,1-dimethylethyl)dimethyl<(5-methyl-2-methylenecyclohexyl)oxy>silane
• 英文别名: tert-butyl-dimethyl-[(1S,5R)-5-methyl-2-methylidenecyclohexyl]oxysilane
• CAS: 145668-40-2
• 化学式: C₁₄H₂₈OSi
• 分子量: 240.461
• InChiKey: LOFFBWFKYDEKIH-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <1S-trans>-(1,1-dimethylethyl)dimethyl<(5-methyl-2-methylenecyclohexyl)oxy>silane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以73%的产率得到trans-(1S)-5-methyl-2-methylenecyclohexanol
  参考文献：
  名称：

  Total synthesis of 1233A

  摘要：

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.

  DOI：

  10.1021/jo00056a013
• 作为产物：
  描述：

  trans-(1R)-2-<<(1,1,-dimethylethyl)dimethylsilyl>oxy>-4-methylenecyclohexanemethanol 在 Wilkinson's catalyst 2-硝基苯基丝氰酸酯 、 三丁基膦 、 氢气 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 25.0~55.0 ℃ 、482.63 kPa 条件下， 反应 18.0h， 生成 <1S-trans>-(1,1-dimethylethyl)dimethyl<(5-methyl-2-methylenecyclohexyl)oxy>silane
  参考文献：
  名称：

  Total synthesis of 1233A

  摘要：

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.

  DOI：

  10.1021/jo00056a013

文献信息

• Total synthesis of 1233A
  作者：P. M. Wovkulich、K. Shankaran、J. Kiegiel、M. R. Uskokovic

  DOI：10.1021/jo00056a013

  日期：1993.2

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.