ethyl (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>naphthalene-1-carboxylate | 143633-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>naphthalene-1-carboxylate
• 英文别名: Ethyl (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-(2,2-dimethylbutyryloxy)-6-[(E)-prop-1-enyl]naphthalene-1-carboxylate；ethyl (1S,2S,4aR,6S,8S,8aS)-8-(2,2-dimethylbutanoyloxy)-2-methyl-6-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
• CAS: 143633-60-7
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: XWGMWGGKRYADIA-ODUJVCJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>naphthalene-1-carboxylate 在 重铬酸吡啶 、 3 A molecular sieve 、 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (1S,3S,4aR,7S,8S,8aS)-8-formyl-1,2,3,4,4a,7,8,8a-octahydro-7-methyl-3-<(E)-prop-1-enyl>-1-naphthalenyl 2,2-dimethylbutyrate
  参考文献：
  名称：

  Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

  摘要：

  The natural product dihydromevinolin, 2, and a series of structurally related 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, 3-6, have been synthesized. The key features are an intramolecular Diels-Alder reaction to form a functionalized decalin skeleton with six asymmetric centers in a stereocontrolled manner, the selective manipulation of the functional groups, and an improved method for the introduction and elaboration of the delta-lactone portion. Analogue 6 was approximately 10-fold more potent than 2 as an inhibitor and was produced in multigram quantities.

  DOI：

  10.1021/jo00047a011
• 作为产物：
  描述：

  (+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone 在 吡啶 、 chromium dichloride 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 3 A molecular sieve 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.33h， 生成 ethyl (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>naphthalene-1-carboxylate
  参考文献：
  名称：

  Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

  摘要：

  The natural product dihydromevinolin, 2, and a series of structurally related 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, 3-6, have been synthesized. The key features are an intramolecular Diels-Alder reaction to form a functionalized decalin skeleton with six asymmetric centers in a stereocontrolled manner, the selective manipulation of the functional groups, and an improved method for the introduction and elaboration of the delta-lactone portion. Analogue 6 was approximately 10-fold more potent than 2 as an inhibitor and was produced in multigram quantities.

  DOI：

  10.1021/jo00047a011