(S)-(E)-6,10-dimethyl-5,9-undecadien-2-yl acetate | 1262015-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(E)-6,10-dimethyl-5,9-undecadien-2-yl acetate
• 英文别名: [(2S,5E)-6,10-dimethylundeca-5,9-dien-2-yl] acetate
• CAS: 1262015-79-1
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: BXGLLMNDXKACMT-UELRPHRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸酐 、 (S)-(E)-6,10-dimethyl-5,9-undecadien-2-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(S)-(E)-6,10-dimethyl-5,9-undecadien-2-yl acetate
  参考文献：
  名称：

  Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae)

  摘要：

  The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(-)-(E)-6,10-dimethy1-5,9-undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-(3) and a mixture of (R)- and (S)-(2) in a ratio of 82.3% and 17.6%, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.024

文献信息

• Male produced pheromone in Tetropium fuscum (F.) and Tetropium cinnamopterum (Kirby) (Coleoptera: Cerambycidae)
  申请人：Silk Peter

  公开号：US20090092577A1

  公开（公告）日：2009-04-09

  Described herein is (E)-6,10-dimethyl-5,9-undecadien-2-ol (geranyl acetol), termed here fuscumol, which has been identified as a male-produced pheromone emitted by Tetropium fuscum (F.) and Tetropium cinnamopterum. Also described are novel derivatives thereof e.g. esters, methods for the synthesis thereof and to a composition comprising fuscumol plus host volatiles e.g. a synthetic blend of monoterpenes plus ethanol, for attracting male and female T. fuscum and female T. cinnamopterum.

  本文描述了(E)-6,10-二甲基-5,9-十一烯-2-醇（香叶醇），在此称为茯烯醇，已被确定为由茶小蠹（Tetropium fuscum (F.)）和肉桂翅小蠹（Tetropium cinnamopterum）所释放的雄性产生的信息素。还描述了其新颖衍生物，例如酯类，其合成方法以及包含茯烯醇和寄主挥发物（例如单萜烃加乙醇的合成混合物）的组合物，用于吸引茶小蠹的雄性和雌性以及肉桂翅小蠹的雌性。
• US8029814B2
  申请人：——

  公开号：US8029814B2

  公开（公告）日：2011-10-04
• Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae)
  作者：Diogo M. Vidal、Marcy G. Fonseca、Paulo H.G. Zarbin

  DOI：10.1016/j.tetlet.2010.10.024

  日期：2010.12

  The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(-)-(E)-6,10-dimethy1-5,9-undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-(3) and a mixture of (R)- and (S)-(2) in a ratio of 82.3% and 17.6%, respectively. (C) 2010 Elsevier Ltd. All rights reserved.