(1R,4aR,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde | 1262283-43-1

• 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,4aR,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
• CAS: 1262283-43-1
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: BXASPXSBNBLFAS-RYLXDESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4aR,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以70%的产率得到(3S)-hydroxypolygodial
  参考文献：
  名称：

  Enantioselective synthesis of 3(S)-hydroxy polygodial derivatives and evaluation of their vanilloid activity

  摘要：

  The enantioselective synthesis of 3(S)-hydroxy polygodial and its acetyl derivative is described. The construction of the 3-hydroxy drimane skeleton was based on the titanium-catalyzed radical cyclization of (10S)-10, 11-epoxy-farnesyl acetate. Only underivatized 3(S)-hydroxy polygodial showed activity in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.002
• 作为产物：
  描述：

  (1R,4aR,6S,8aS)-(+)-6-(tert-butyldimethylsilyloxy)-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1,2-naphthalenedimethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.92h， 以76%的产率得到(1R,4aR,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
  参考文献：
  名称：

  Enantioselective synthesis of 3(S)-hydroxy polygodial derivatives and evaluation of their vanilloid activity

  摘要：

  The enantioselective synthesis of 3(S)-hydroxy polygodial and its acetyl derivative is described. The construction of the 3-hydroxy drimane skeleton was based on the titanium-catalyzed radical cyclization of (10S)-10, 11-epoxy-farnesyl acetate. Only underivatized 3(S)-hydroxy polygodial showed activity in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.002

文献信息

• Enantioselective synthesis of 3(S)-hydroxy polygodial derivatives and evaluation of their vanilloid activity
  作者：Mariantonietta D’Acunto、Carmela Della Monica、Irene Izzo、Luciano De Petrocellis、Vincenzo di Marzo、Aldo Spinella

  DOI：10.1016/j.tet.2010.11.002

  日期：2010.12

  The enantioselective synthesis of 3(S)-hydroxy polygodial and its acetyl derivative is described. The construction of the 3-hydroxy drimane skeleton was based on the titanium-catalyzed radical cyclization of (10S)-10, 11-epoxy-farnesyl acetate. Only underivatized 3(S)-hydroxy polygodial showed activity in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (C) 2010 Elsevier Ltd. All rights reserved.