(E)-3-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]prop-2-enal | 144225-35-4

• 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: (E)-3-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]prop-2-enal
• CAS: 144225-35-4
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: MNRXYWAPTURPNC-KMSXPONXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]prop-2-enal 在 sodium methylate 、 lithium diisopropyl amide 作用下， 反应 5.58h， 生成 methyl (E,3S)-5-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]-3-hydroxypent-4-enoate
  参考文献：
  名称：

  C-2 dimethyl seco-mevinic acids. Synthesis of monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone.

  摘要：

  An efficient preparation of novel monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone is reported. Utilizing this chiral carbon pool, the C-2 dimethyl seco-mevinic acid 3a was prepared in 17 steps and 5.2 % overall yield. The key chiral intermediate aldehyde 10a was prepared via a short and efficient synthetic sequence (six steps, 27% yield) from (R)-(-)-carvone. The appropriate chirality of the diol acid side chain was secured by employing the chiral acetate synthon ''(S)-HYTRA'' and by performing a stereoselective 1,3-syn reduction on the beta-hydroxy ketone 19. Structural requirements at the C-2 position are rather stringent, and deletion of or addition of an extra methyl group are both unacceptable modifications for this novel class of monocyclic HMG-CoA reductase inhibitors.

  DOI：

  10.1021/jo00052a031
• 作为产物：
  描述：

  (5R)-5-isopropenyl-2,2-dimethylcyclohexanone 在 Wilkinson's catalyst 正丁基锂 、 高氯酸 、 氢气 、 三乙胺 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.25h， 生成 (E)-3-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]prop-2-enal
  参考文献：
  名称：

  C-2 dimethyl seco-mevinic acids. Synthesis of monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone.

  摘要：

  An efficient preparation of novel monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone is reported. Utilizing this chiral carbon pool, the C-2 dimethyl seco-mevinic acid 3a was prepared in 17 steps and 5.2 % overall yield. The key chiral intermediate aldehyde 10a was prepared via a short and efficient synthetic sequence (six steps, 27% yield) from (R)-(-)-carvone. The appropriate chirality of the diol acid side chain was secured by employing the chiral acetate synthon ''(S)-HYTRA'' and by performing a stereoselective 1,3-syn reduction on the beta-hydroxy ketone 19. Structural requirements at the C-2 position are rather stringent, and deletion of or addition of an extra methyl group are both unacceptable modifications for this novel class of monocyclic HMG-CoA reductase inhibitors.

  DOI：

  10.1021/jo00052a031