1(R)-Hydroxypolygodial | 143840-14-6

• 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: 1(R)-Hydroxypolygodial
• 英文别名: (1R,4aS,8R,8aS)-8-hydroxy-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
• CAS: 143840-14-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: LGWVDHGRABZBKL-RMRHIDDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1(R)-Hydroxypolygodial 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以82%的产率得到(1S,4aS,8R,8aS)-8-hydroxy-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
• 作为产物：
  描述：

  (R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol 在 palladium on activated charcoal 咪唑 、 草酰氯 、 氢氟酸 、 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 、 乙腈 为溶剂， 反应 65.0h， 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

文献信息

• Enantioselective synthesis and vanilloid activity evaluation of 1-β-(p-methoxycinnamoyl)polygodial, an antinociceptive compound from Drymis winteri barks
  作者：Carmela Della Monica、Luciano De Petrocellis、Vincenzo Di Marzo、Raffaella Landi、Irene Izzo、Aldo Spinella

  DOI：10.1016/j.bmcl.2007.10.001

  日期：2007.12

  A simple strategy is outlined for preparation of the antinociceptive 1-beta-(p-methoxycinnamoyl) polygodial, isolated from Drymis winteri barks. The synthesized compound showed vanilloid activity. (c) 2007 Elsevier Ltd. All rights reserved.