(1R,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester | 854764-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1R,8R,8aR)-8-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-1,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate
• CAS: 854764-51-5
• 化学式: C₂₃H₃₈O₅Si
• 分子量: 422.637
• InChiKey: ZBXMREXPUXFKBE-PMAPCBKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 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：

  (1R,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal 草酰氯 、 氢氟酸 、 氢气 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 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 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到(1R,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydronaphthalene-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 1(R)-hydroxypolygodial

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.04.020