| 143633-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 143633-62-9
• 化学式: C₂₆H₄₄O₅Si
• 分子量: 464.718
• InChiKey: YCLCUASZSXCTTF-BPYKOXKGSA-N

物化性质

• 沸点：
  524.0±50.0 °C(predicted)
• 密度：
  1.034±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-甲基丁酰氯 、 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.0h， 以30%的产率得到methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate
  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)-8-<(tert-butyldimethylsilyl)oxy>-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxaldehyde 在 氢氟酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成
  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