cis-(1R,3R)-3-methyl-6-methylenecyclohexanol | 145773-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-(1R,3R)-3-methyl-6-methylenecyclohexanol
• 英文别名: Cyclohexanol, 5-methyl-2-methylene-, (1R-cis)-；(1R,5R)-5-methyl-2-methylidenecyclohexan-1-ol
• CAS: 145773-23-5
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: CBPBBXYEZYIFQC-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-(1R,3R)-3-methyl-6-methylenecyclohexanol 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 、 对硝基苯甲酸 作用下， 生成 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：

  长叶薄荷酮 在 sodium tetrahydroborate 、 cerium(III) chloride 、 二甲基硫 、 potassium tert-butylate 、 臭氧 作用下， 生成 cis-(1R,3R)-3-methyl-6-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

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.