(-)-axenol | 68945-58-4

• 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: (-)-axenol
• 英文别名: (5S,6R,9S,10S)-3,6-dimethyl-9-propan-2-ylspiro[4.5]dec-3-en-10-ol
• CAS: 68945-58-4
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: MYLXGCVCCZCOHU-CBBWQLFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-axenol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到(5S,7S,10R)-(+)-7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-one
  参考文献：
  名称：

  Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone

  摘要：

  The synthesis of the spirocyclic sesquiterpenes (-)-gleenol and (-)-axenol in enantiomerically pure form has been achieved starting from R-(-)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3-tiimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.025
• 作为产物：
  描述：

  (1R,2RS,4S)-2-Formyl-2-(3-oxobutyl)-p-menthan-3-on 在 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride 、 potassium tert-butylate 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 95.0h， 生成 (-)-axenol
  参考文献：
  名称：

  螺[4.5]癸烷倍半萜烯（-）-烯醇的短全合成

  摘要：

  螺环倍半萜烯（-）-烯醇从（-）-甲酮经二烯烃开始，分五步制备。最终的螺环系统是使用烯烃复分解反应制得的。将得到的酮选择性地还原为天然产物。

  DOI：

  10.1016/s0040-4020(02)00336-8

文献信息

• Total Synthesis of (.+-.)-Gleenol and (.+-.)-Axenol via a Functionalized Spiro[4.5]decane
  作者：Atsuo Nakazaki、Tomohiro Era、Susumu Kobayashi

  DOI：10.1248/cpb.55.1606

  日期：——

  was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in excellent yield, installation of the C7 isopropyl group via ketene dithioacetal instead of direct alkylation and a diastereoselective reduction of ketone under the Birch conditions.

  生物学上重要的黄烷倍半萜烯，格列醇（1）和烯丙醇（2）的全合成是通过容易获得的螺[4.5]癸烷完成的。1和2合成的关键特征包括克莱森重排，以优异的收率提供多官能化的螺[4.5]癸烷4作为单一非对映异构体，通过乙烯酮二硫缩醛而不是直接烷基化安装C7异丙基和非对映选择性还原在桦木条件下的酮
• Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone
  作者：Gonzalo Blay、Ana M. Collado、Begoña García、José R. Pedro

  DOI：10.1016/j.tet.2005.09.025

  日期：2005.11

  The synthesis of the spirocyclic sesquiterpenes (-)-gleenol and (-)-axenol in enantiomerically pure form has been achieved starting from R-(-)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3-tiimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol. (c) 2005 Elsevier Ltd. All rights reserved.
• Short total synthesis of the spiro[4.5]decane sesquiterpene (−)-gleenol
  作者：Kai Oesterreich、Dietrich Spitzner

  DOI：10.1016/s0040-4020(02)00336-8

  日期：2002.5

  The spirocyclic sesquiterpene (−)-gleenol was prepared in five steps starting from (−)-methone via a di-olefin. The final spiro-ring system was made using the olefin metathesis reaction. The resulting ketone was selectively reduced to the natural product.

  螺环倍半萜烯（-）-烯醇从（-）-甲酮经二烯烃开始，分五步制备。最终的螺环系统是使用烯烃复分解反应制得的。将得到的酮选择性地还原为天然产物。