(1R,4aS,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde | 854764-53-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,4aS,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
• CAS: 854764-53-7
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: QERPVYKBRGJBBY-LXGFNABISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,4aS,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以79%的产率得到1(R)-Hydroxypolygodial
  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：

  (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 草酰氯 、 氢气 、 二异丁基氢化铝 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (1R,4aS,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
  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