(8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-3,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester | 854764-46-8

• 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: (8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-3,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-3,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate
• CAS: 854764-46-8
• 化学式: C₂₃H₃₈O₅Si
• 分子量: 422.637
• InChiKey: WHNUWBDTGCNHDF-UZUQRXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-3,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 17.0h， 生成 (1R,4aS,8R,8aS)-[8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]methanol
  参考文献：
  名称：

  Enantioselective synthesis of 1-(R)-hydroxypolygodial and its 9α epimer, 1-(R)-hydroxyisotadeonal

  摘要：

  The enantioselective synthesis of 1-(R)-hydroxypolygodial and its epimer at C-9 is described. alpha-Ionone was the starting material. Key steps of these syntheses included a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction. No vanilloid activity was detected for both compounds in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.059
• 作为产物：
  描述：

  3-乙烯基-2,4,4-三甲基环己-2-烯-1-酮 在 咪唑 、 硼烷四氢呋喃络合物 、 (S)-methyl-oxazaborolidine 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 (8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-3,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 1-(R)-hydroxypolygodial and its 9α epimer, 1-(R)-hydroxyisotadeonal

  摘要：

  The enantioselective synthesis of 1-(R)-hydroxypolygodial and its epimer at C-9 is described. alpha-Ionone was the starting material. Key steps of these syntheses included a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction. No vanilloid activity was detected for both compounds in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.059

文献信息

• Enantioselective synthesis of 1(R)-hydroxypolygodial
  作者：Carmela Della Monica、Giorgio Della Sala、Deborah D’Urso、Irene Izzo、Aldo Spinella

  DOI：10.1016/j.tetlet.2005.04.020

  日期：2005.6

  Enantioselective preparation of 1(R)-hydroxypolygodial (5) has been achieved starting from alpha-ionone through a synthetic strategy involving a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction as key steps. (c) 2005 Elsevier Ltd. All rights reserved.