(3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-<2-(ethoxycarbonyl)-(E)-ethenyl>tetrahydrofuran-2-one | 102418-84-8

• 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: (3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-<2-(ethoxycarbonyl)-(E)-ethenyl>tetrahydrofuran-2-one
• 英文别名: (3S,5S)-3-(2'(E),4'(E)-hexadienyl)-5-[2-(ethoxycarbonyl)-(E)-ethenyl]tetrahydrofuran-2-one；ethyl (E)-3-[(2S,4S)-4-[(2E,4E)-hexa-2,4-dienyl]-5-oxooxolan-2-yl]prop-2-enoate
• CAS: 102418-84-8
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: LSGUMLNDWRXFMX-ZIMONONYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-<2-(ethoxycarbonyl)-(E)-ethenyl>tetrahydrofuran-2-one 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 均三甲苯 为溶剂， 反应 264.0h， 以73%的产率得到(+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone
  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：

  sorbyl bromide 在 草酰氯 、 溴代叔丁烷 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.42h， 生成 (3S,5S)-3-<2'(E),4'(E)-hexadienyl>-5-<2-(ethoxycarbonyl)-(E)-ethenyl>tetrahydrofuran-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

文献信息

• A stereochemically controlled intramolecular Diels–Alder approach to the octahydronaphthalene fragment of dihydromevinolin
  作者：Alan H. Davidson、Chris D. Floyd、Andrew J. Jones、Peter L. Myers

  DOI：10.1039/c39850001662

  日期：——

  An enantiospecific route to the octahydronaphthalene (22) from L-glutamic acid is described: the key step is the intramolecular Diels–Alder reaction (19) to (22).

  描述了从L-谷氨酸到八氢萘（22）的对映体特异性路线：关键步骤是分子内Diels-Alder反应（19）至（22）。
• 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.