drim-8-en-11-ol acetate | 157722-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: drim-8-en-11-ol acetate
• 英文别名: 11-acetoxy-8-drimene；isodrimenyl acetate；[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl acetate
• CAS: 157722-62-8
• 化学式: C₁₇H₂₈O₂
• 分子量: 264.408
• InChiKey: AHHGTQIJEIDRFP-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  drim-8-en-11-ol acetate 在 sodium chromate(VI) 、 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 3.5h， 以91%的产率得到11-acetoxydrim-8(9)-en-7-one
  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：

  ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl acetate 在 2,3,5-三甲基吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 drim-8-en-11-ol acetate
  参考文献：
  名称：

  由（-）-紫杉醇合成具有生物活性的drimanes

  摘要：

  描述了对映体特异性的合成方法，它是生物活性drimanes合成中的关键中间体乙酸二烯基乙酸酯（8）和从香紫苏醇（1）中提取的强效鱼类拒食剂乙酸白三烷基酯（14）。还显示了由乙酸白烷基酯（14）的短而有效的合成多角体（22）。

  DOI：

  10.1016/s0040-4039(00)76667-6

文献信息

• Elimination of C-8-functional groups from driman-8α,11-diol-11-monoacetate and-diacetate
  作者：K. I. Kuchkova、A. N. Aryku、A. N. Barba、P. F. Vlad

  DOI：10.1007/s10600-007-0151-9

  日期：2007.7

  The dehydration products of driman-8α,11-diol-11-monoacetate that are formed upon reaction with several dehydrating agents and the products from elimination of the C-8 acetoxy group in driman-8α,11-diol diacetate were investigated in detail. A new effective synthesis of drimenylacetate from driman-8α, 11-diol-11-monoacetate by its regioselective dehydration using methanesulfonic acid trimethylsilyl ether was developed.

  研究了与几种脱水剂反应生成的driman-8α,11-diol-11-monoacetate的脱水产物以及从driman-8α,11-diol diacetate中去除C-8乙酰氧基所产生的产物。开发了一种通过使用甲磺酸三甲基硅基醚对driman-8α,11-diol-11-monoacetate进行区域选择性脱水的新有效合成方法，生成drimenylacetate。
• 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 biologically active drimanes and homodrimanes from (−)-sclareol
  作者：Alejandro F. Barrero、Enrique A. Manzaneda、Joaquin Altarejos、Sofía Salido、Jose M. Ramos、M.S.J. Simmonds、W.M. Blaney

  DOI：10.1016/0040-4020(95)00370-n

  日期：1995.7

  Three drimanes, polygodial (2), albicanyl acerate (3) and 7-oxo-8,12-drimen-11-al (5), and two homodrimanes, 13,14,15,16-tetranorlabd-7-en-12,17-dial (6) and 7-oxo-13,14,15,16-tetranorlabd-8(17)-en-12-al (7), were synthesized from (-)-sclareol (1), and their antifeedant, antitumor and antimicrobial properties tested. In mast cases, 6 and 7 were found to be more active than 2.
• Synthesis of (−)-Hyatellaquinone and Revision of Absolute Configuration of Naturally Occurring (+)-Hyatellaquinone
  作者：Stéphane Poigny、Thomas Huor、Michèle Guyot、Mohammad Samadi

  DOI：10.1021/jo9910886

  日期：1999.12.1
• Synthesis of biologically active drimanes from (−)-sclareol
  作者：Alejandro F. Barrero、Enrique Alvarez-Manzaneda、Joaquín Altarejos、Sofía Salido、José M. Ramos

  DOI：10.1016/s0040-4039(00)76667-6

  日期：1994.5

  The enantiospecific synthesis of drimenyl acetate (8), a key intermediate in the synthesis of biologically active drimanes, and albicanyl acetate (14), potent fish antifeedant, from sclareol (1), are described. Also a short and efficient synthesis of polygodial (22), from albicanyl acetate (14), is shown.

  描述了对映体特异性的合成方法，它是生物活性drimanes合成中的关键中间体乙酸二烯基乙酸酯（8）和从香紫苏醇（1）中提取的强效鱼类拒食剂乙酸白三烷基酯（14）。还显示了由乙酸白烷基酯（14）的短而有效的合成多角体（22）。