(1S,2S,3S,4S,7R,9S)-4,9-Dimethyl-10-oxo-11-oxa-tricyclo[7.2.1.0^2,7]dodec-5-ene-3-carboxylic acid ethyl ester | 1027013-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,2S,3S,4S,7R,9S)-4,9-Dimethyl-10-oxo-11-oxa-tricyclo[7.2.1.0^2,7]dodec-5-ene-3-carboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S,3S,4S,7R,9S)-4,9-dimethyl-10-oxo-11-oxatricyclo[7.2.1.02,7]dodec-5-ene-3-carboxylate
• CAS: 1027013-68-8
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: QXJDUTZWIYIIJO-UVXMZDTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (1S,2S,3S,4S,7R,9S)-4,9-Dimethyl-10-oxo-11-oxa-tricyclo[7.2.1.0^2,7]dodec-5-ene-3-carboxylic acid ethyl ester 在 2,6-二甲基吡啶 、 sodium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,2S,4aR,6S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1,6-dicarboxylic acid 1-ethyl ester 6-methyl ester
  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：

  (E)-3-[(2S,4S)-4-((2E,4E)-Hexa-2,4-dienyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-acrylic acid ethyl ester 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 11.0h， 生成 (1S,2S,3S,4S,7R,9S)-4,9-Dimethyl-10-oxo-11-oxa-tricyclo[7.2.1.0^2,7]dodec-5-ene-3-carboxylic acid ethyl ester
  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.