[(1S,3S,4aR,7S,8S,8aS)-8-(hydroxymethyl)-7-methyl-3-[(Z)-prop-1-enyl]-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate | 1027510-30-0

• 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: [(1S,3S,4aR,7S,8S,8aS)-8-(hydroxymethyl)-7-methyl-3-[(Z)-prop-1-enyl]-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• CAS: 1027510-30-0
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: GWQYCMRLWPSZPE-YAEKKFQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S,3S,4aR,7S,8S,8aS)-8-(hydroxymethyl)-7-methyl-3-[(Z)-prop-1-enyl]-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate 在 碲化氢 、 sodium tetrahydroborate 、 重铬酸吡啶 、 3 A molecular sieve 、 二乙基甲氧基硼烷 、 氢氟酸 、 氯化铵 、 溶剂黄146 、 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 80.0h， 生成 (1S,2S,4aR,6S,8S,8aS,4'R,6'R,2''S)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2''-methylbutyryl)oxy>-6-<(Z)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one
  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 2,6-二甲基吡啶 、 草酰氯 、 氢氟酸 、 sodium hexamethyldisilazane 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 45.25h， 生成 [(1S,3S,4aR,7S,8S,8aS)-8-(hydroxymethyl)-7-methyl-3-[(Z)-prop-1-enyl]-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2S)-2-methylbutanoate
  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

文献信息

• Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors
  作者：Christopher M. Blackwell、Alan H. Davidson、Steven B. Launchbury、Christopher N. Lewis、Elizabeth M. Morrice、Maxwell M. Reeve、Jonathon A. R. Roffey、Andrew S. Tipping、Richard S. Todd

  DOI：10.1021/jo00047a011

  日期：1992.10

  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.