(3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene | 68831-82-3

• 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: (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene
• 英文别名: (1R,4R)-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-ol
• CAS: 68831-82-3
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: YTPJSSUCMUKHHN-JXSGWAFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 6.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,4R)-3,5,5-trimethyl-4-[(E)-(R)-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-cyclohex-2-enyl ester
  参考文献：
  名称：

  Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui

  摘要：

  Twelve C-13 nor-isoprenoids have been isolated from the leaves of Cestrum parqui (Solanaceae). The structure (2R,6R,9R)-2,9-dihydroxy-4-megastigmen-3-one has been assigned to the new compound. All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa L. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2003.11.018
• 作为产物：
  描述：

  (6R)-6-[(4-methoxyphenyl)methoxy]-2-methylhept-2-en-4-ol 在 吡啶 、 2,6-二甲基吡啶 、 正丁基锂 、 硼烷四氢呋喃络合物 、 mercury(II) diacetate 、 palladium diacetate 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) 、 三乙胺 、 红铝 、 三(邻甲基苯基)磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 68.42h， 生成 (3R,6R,7E,9R)-3,9-dihydroxy-4,7-megastigmadiene
  参考文献：
  名称：

  Enantiocontrolled access to the ionone type bisnorsesquiterpenes. Total syntheses of 3-oxo-α-ionol and related natural products

  摘要：

  The enantiocontrolled total syntheses of three ionone type bisnorsesquiterpenes have been accomplished employing a highly diastereoselective intramolecular Heck reaction as the key step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.151

文献信息

• Behr,D. et al., Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry, 1978, vol. B32, # 6, p. 391 - 394
  作者：Behr,D. et al.

  DOI：——

  日期：——
• Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui
  作者：Brigida D'Abrosca、Marina DellaGreca、Antonio Fiorentino、Pietro Monaco、Palma Oriano、Fabio Temussi

  DOI：10.1016/j.phytochem.2003.11.018

  日期：2004.2

  Twelve C-13 nor-isoprenoids have been isolated from the leaves of Cestrum parqui (Solanaceae). The structure (2R,6R,9R)-2,9-dihydroxy-4-megastigmen-3-one has been assigned to the new compound. All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa L. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantiocontrolled access to the ionone type bisnorsesquiterpenes. Total syntheses of 3-oxo-α-ionol and related natural products
  作者：Daisuke Kikuchi、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2011.10.151

  日期：2012.1

  The enantiocontrolled total syntheses of three ionone type bisnorsesquiterpenes have been accomplished employing a highly diastereoselective intramolecular Heck reaction as the key step. (C) 2011 Elsevier Ltd. All rights reserved.