(1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate | 108944-86-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate
• 英文别名: (+)-(8S)-8-hydroxy-12-nordrimanic acid methyl ester；methyl (1R,2S,4aS,8aS)-2-hydroxy-5,5,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalene-1-carboxylate
• CAS: 108944-86-1
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: PNORERWVNDPBJT-OHTBPHCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 PhP(+)MeBr(-) 、 sodium hydride 、 lithium 1-butanethiolate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 吡啶 、 六甲基磷酰三胺 、 二甲基亚砜 、 丙酮 、 苯 为溶剂， 反应 75.67h， 生成 (-)-ent-zonarol
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Zonarol. A Fungitoxic Hydroquinone from the Brown Seaweed Dictyoptfris Zonarioides(1)

  摘要：

  AbstractA total synthesis of both the enantiomers of zonarol 1 was accomplished. Measurements of the ORD‐CD spectra of two bicyclic intermediates coupled with direct comparison of the natural and synthetic zonarol 1 established the absolute configuration of the naturally occurring (+)‐zonarol 1 as 1R, 4aR, 8aR.

  DOI：

  10.1002/bscb.19860950906
• 作为产物：
  描述：

  香叶基丙酮 在 sodium tetrahydroborate 、 三氯硅烷 、 水 、 四氯化锡 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 40.5h， 生成 (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Zonarol. A Fungitoxic Hydroquinone from the Brown Seaweed Dictyoptfris Zonarioides(1)

  摘要：

  AbstractA total synthesis of both the enantiomers of zonarol 1 was accomplished. Measurements of the ORD‐CD spectra of two bicyclic intermediates coupled with direct comparison of the natural and synthetic zonarol 1 established the absolute configuration of the naturally occurring (+)‐zonarol 1 as 1R, 4aR, 8aR.

  DOI：

  10.1002/bscb.19860950906

文献信息

• Total synthesis of two 12-nordrimanes and the pharmacological active sesquiterpene hydroquinone yahazunol
  作者：Thorsten Laube、Winfried Beil、Karlheinz Seifert

  DOI：10.1016/j.tet.2004.11.059

  日期：2005.1

  The synthesis of two 12-nordrimanes and yahazunol was achieved via 8-oxo-12-nordrimanic acid methyl ester. The cytotoxic activity of yahazunol and seven other sesquiterpene hydroquinones and sesquiterpene quinones has been determined. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Absolute Configuration of Zonarol. A Fungitoxic Hydroquinone from the Brown Seaweed Dictyoptfris Zonarioides(1)
  作者：Kenji Mori、Makoto Komatsu

  DOI：10.1002/bscb.19860950906

  日期：——

  AbstractA total synthesis of both the enantiomers of zonarol 1 was accomplished. Measurements of the ORD‐CD spectra of two bicyclic intermediates coupled with direct comparison of the natural and synthetic zonarol 1 established the absolute configuration of the naturally occurring (+)‐zonarol 1 as 1R, 4aR, 8aR.