(+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate | 102299-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate
• 英文别名: 1-O-ethyl 6-O-methyl (1S,2S,4aR,6S,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1,6-dicarboxylate
• CAS: 102299-03-6
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: PQWKMNUMPNERCA-LQSBQDLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate 在 吡啶 、 chromium dichloride 、 4-二甲氨基吡啶 、 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 48.33h， 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：

  甲醇 、 (+)-(1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6,8-naphthalenecarbolactone 在 sodium hexamethyldisilazane 作用下， 反应 2.0h， 以61%的产率得到(+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-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

文献信息

• The enantiospecific synthesis of dihydromevinolin from L-glutamic acid
  作者：Alan H. Davidson、Andrew J. Jones、Chris D. Floyd、Christopher Lewis、Peter L. Myers

  DOI：10.1039/c39870001786

  日期：——

  An enantiospecific synthesis of the diol (3), a compound which has previously been converted into dihydromevinolin, is reported.

  据报道二醇（3）的对映体特异性合成，该化合物先前已被转化为二氢甲基乙烯基。