drim-7-ene-9α,11-diol | 149286-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: drim-7-ene-9α,11-diol
• 英文别名: 7-drimen-9α,11-diol；drim-7en-9α,11-diol；(1R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-4a,6,7,8-tetrahydro-4H-naphthalen-1-ol
• CAS: 149286-42-0
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: ZZWGQQYPPYOXSR-AEGPPILISA-N

物化性质

• 熔点：
  82-83 °C(Solvent: Hexane)
• 沸点：
  340.1±17.0 °C(predicted)
• 密度：
  1.006±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  drim-7-ene-9α,11-diol 在 吡啶 、 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 2.83h， 生成 (-)-drim-7-ene-9α,11,12-triol
  参考文献：
  名称：

  Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

  摘要：

  The first syntheses are reported for recently isolated drimanes 11,12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.

  DOI：

  10.1021/np990140q
• 作为产物：
  描述：

  11-acetoxydrim-8(9)-en-7-one 在 sodium hydroxide 、 双氧水 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.5h， 生成 drim-7-ene-9α,11-diol
  参考文献：
  名称：

  Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

  摘要：

  The first syntheses are reported for recently isolated drimanes 11,12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.

  DOI：

  10.1021/np990140q

文献信息

• Convenient synthesis of drimenol and its oxidation with selenium dioxide
  作者：K. I. Kuchkova、A. N. Aricu、I. P. Dragalin、P. F. Vlad

  DOI：10.1007/s11172-005-0203-x

  日期：2004.12

  A convenient synthesis of drimenol by treatment of readily available drimane-8α, 11-diol 11-monoacetate with sulfuric acid in ethanol under mild conditions was developed. Oxidation of drimenol with selenium dioxide gives known drim-7-ene-9α, 11-diol and drim-7-ene-11,12-diol as the major products.

  通过在温和条件下用硫酸在乙醇中处理容易获得的 drimane-8α, 11-diol 11-monoacetate，开发了一种方便的 drimenol 合成方法。用二氧化硒氧化 drimenol 得到已知的 drim-7-ene-9α, 11-diol 和 drim-7-ene-11,12-diol 作为主要产物。
• Synthesis of Drim-7,9(11)-diene and Its Hydroxylated Derivatives
  作者：Pavel F. Vlad、Alexandru G. Ciocarlan、Mihai N. Coltsa、Alexandr V. Baranovsky、Natalya B. Khripach

  DOI：10.1080/00397910802241399

  日期：2008.10.28

  efficient synthesis of drim-7,9(11)-diene and its hydroxylated derivates from drim-8-en-7-one. Reduction of this ketone with NaBO4 in the presence of CeCl3 · 7H2O afforded regio- and stereoselectively drim-8-en-7β-ol in a high yield. Its dehydration with H2SO4 under mild conditions led to drim-7,9(11)-diene. Noncatalytic oxidation of drim-7,9(11)-diene with OsO4 and the catalytic oxidation with the

  摘要 本文描述了一种新型高效合成 drim-7,9(11)-二烯及其衍生自 drim-8-en-7-one 的羟基化衍生物。在CeCl3·7H2O 存在下用NaBO4 还原该酮以高产率提供区域选择性和立体选择性drim-8-en-7β-ol。其在温和条件下用 H2SO4 脱水生成 drim-7,9(11)-二烯。drim-7,9(11)-diene 与 OsO4 的非催化氧化和 OsO4-NMO 对的催化氧化得到高产率，取决于条件，driman-7β,8β,9α,11-tetraol 或其混合物使用 drim-7-en-9α,11-diol 和 drim-9(11​​)-en-7α,8α-diol。在最佳条件下，这些二醇的总收率达到了 89%。drim-7-en-9α,11-二醇和 drim-9(11​​)-en-7α,8α-二醇与 OsO4 的单独非催化氧化得到 driman-7α,8α
• Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions
  作者：Alejandro F. Barrero、Enrique J. Alvarez-Manzaneda、R. Chahboun

  DOI：10.1016/s0040-4039(00)00071-x

  日期：2000.3

  1,1-Disubstituted 1,2-diols are efficiently converted into carbonyl compounds by reaction with triphenylphosphine and diethyl azodicarboxylate. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol
  作者：A. F. Barrero、M. Cortés、E. A. Manzaneda、E. Cabrera、R. Chahboun、M. Lara、A. R. Rivas

  DOI：10.1021/np990140q

  日期：1999.11.1

  The first syntheses are reported for recently isolated drimanes 11,12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.