(+)-(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-1-(hydroxymethyl)-2,6-dimethylnaphthalene | 116180-69-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-1-(hydroxymethyl)-2,6-dimethylnaphthalene
• 英文别名: (1S,2S,4aR,6S,8S,8aS)-2,6-dimethyl-1-(hydroxymethyl)-8-hydroxy-1,2,4a,5,6,7,8,8a-octahydronaphthalene；(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2,6-dimethyl-1-naphthalenemethanol；(1S,3S,4aR,7S,8S,8aS)-8-(hydroxymethyl)-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol
• CAS: 116180-69-9
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: XCNYIXDPELFDJB-JIQZXMICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-α-甲氧基苯乙酸 、 (+)-(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-1-(hydroxymethyl)-2,6-dimethylnaphthalene 生成 (1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene
  参考文献：
  名称：

  从L-谷氨酸对映体合成二氢美诺灵

  摘要：

  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。

  DOI：

  10.1039/c39870001786
• 作为产物：
  描述：

  (1S,2S,4aR,8RS,8aS)-1-benzyloxymethyl-1,2,4a,5,8,8a-hexahydro-2-methyl-8-naphthol 在 sodium hydroxide 、 copper(l) iodide 、 重铬酸吡啶 、 氨 、 双氧水 、 lithium 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 62.58h， 生成 (+)-(1S,2S,4aR,6S,8S,8aS)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-1-(hydroxymethyl)-2,6-dimethylnaphthalene
  参考文献：
  名称：

  Asymmetric synthesis of the hydronaphthalene moieties of mevinic acids

  摘要：

  The hydronaphthalene moieties of mevinic acids are synthesized enantioselectively by using the asymmetric intramolecular Diels-Alder reaction catalyzed by a chiral titanium reagent.

  DOI：

  10.1016/s0957-4166(00)80028-2

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.
• Synthetic studies on the mevinic acids using the chiron approach: total synthesis of (+)-dihydromevinolin
  作者：Stephen Hanessian、Patrick J. Roy、Marino Petrini、Paul J. Hodges、Romano Di Fabio、Germano Carganico

  DOI：10.1021/jo00309a022

  日期：1990.10
• HANESSIAN, STEPHEN;ROY, PATRICK J.;PETRINI, MARINO;HODGES, PAUL J.;DI, FA+, J. ORG. CHEM., 55,(1990) N2, C. 5766-5777
  作者：HANESSIAN, STEPHEN、ROY, PATRICK J.、PETRINI, MARINO、HODGES, PAUL J.、DI, FA+

  DOI：——

  日期：——