(1,5,5-trimethylcyclopent-2-en-1-yl)methanol | 1160363-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,5,5-trimethylcyclopent-2-en-1-yl)methanol
• 英文别名: (1,5,5-trimethylcyclopent-2-enyl)methanol
• CAS: 1160363-70-1
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: DQSRXKVJHQLASD-UHFFFAOYSA-N

物化性质

• 熔点：
  74-75 °C
• 沸点：
  182.3±9.0 °C(Predicted)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (1,5,5-trimethylcyclopent-2-en-1-yl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 1,5,5-trimethylcyclopent-2-ene-1-carbaldehyde
  参考文献：
  名称：

  Sex Pheromone of the Longtailed Mealybug: A New Class of Monoterpene Structure

  摘要：

  The sex pheromone of the longtailed mealybug, identified as 2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate, represents the first example of a new monoterpenoid skeleton. A [2,3]-sigmatropic rearrangement was used in a key step during construction of the sterically congested tetraalkylcylopentene framework.

  DOI：

  10.1021/ol802164v
• 作为产物：
  描述：

  1,5,5-trimethylcyclopent-2-enecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (1,5,5-trimethylcyclopent-2-en-1-yl)methanol
  参考文献：
  名称：

  Synthesis of the Pheromone of the Longtailed Mealybug, a Sterically Congested, Irregular Monoterpenoid

  摘要：

  A straightforward and scaleable Synthesis of the sterically congested pheromone of the longtailed mealybug, with two adjacent quarternary carbons in a cyclopentene ring, was accomplished in 13.5% overall yield. Key steps included regiospecific cyclization of an alpha-diazo-beta-ketoester to build the cyclopentane ring, followed by reduction of the enol triflate of the ketone to place the double bond.

  DOI：

  10.1021/jo901505y

文献信息

• [EN] ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ENANTIOMERS OF SEX PHEROMONES<br/>[FR] PROCÉDÉ ÉNANTIOSÉLECTIF POUR LA PRÉPARATION D'ÉNANTIOMÈRES DE PHÉROMONES SEXUELLES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014115172A1

  公开（公告）日：2014-07-31

  The invention disclosed herein relates to an enantioselective process for preparation of biologically active (R) and (S) enantiomers of sex pheromones of the long-tailed Mealybug with high enantiopurity having significant biological activity. Further, the invention provides absolute configuration of synthesized R and S enantiomers.(I)

  本发明涉及一种对长尾粉蚧的性信息素的(R)和(S)对映体进行高对映纯度的选择性合成过程，这些性信息素具有显著的生物活性。此外，该发明提供了合成的R和S对映体的绝对构型。(I)
• ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ENANTIOMERS OF SEX PHEROMONES
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20150361025A1

  公开（公告）日：2015-12-17

  The invention disclosed herein relates to an enantioselective process for preparation of biologically active (R) and (S) enantiomers of sex pheromones of the long-tailed Mealybug with high enantiopurity having significant biological activity. Further, the invention provides absolute configuration of synthesized R and S enantiomers.(I)

  本发明涉及一种手性选择性制备长尾粉介壳虫生物活性(R)和(S)对映体性别信息素的过程，具有高对映纯度和显著的生物活性。此外，本发明提供了合成的R和S对映体的绝对构型。(I)
• US9598346B2
  申请人：——

  公开号：US9598346B2

  公开（公告）日：2017-03-21
• Synthesis of the Pheromone of the Longtailed Mealybug, a Sterically Congested, Irregular Monoterpenoid
  作者：Yunfan Zou、Jocelyn G. Millar

  DOI：10.1021/jo901505y

  日期：2009.9.18

  A straightforward and scaleable Synthesis of the sterically congested pheromone of the longtailed mealybug, with two adjacent quarternary carbons in a cyclopentene ring, was accomplished in 13.5% overall yield. Key steps included regiospecific cyclization of an alpha-diazo-beta-ketoester to build the cyclopentane ring, followed by reduction of the enol triflate of the ketone to place the double bond.
• Sex Pheromone of the Longtailed Mealybug: A New Class of Monoterpene Structure
  作者：Jocelyn G. Millar、Jardel A. Moreira、J. Steven McElfresh、Kent M. Daane、Amy S. Freund

  DOI：10.1021/ol802164v

  日期：2009.6.18

  The sex pheromone of the longtailed mealybug, identified as 2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethyl acetate, represents the first example of a new monoterpenoid skeleton. A [2,3]-sigmatropic rearrangement was used in a key step during construction of the sterically congested tetraalkylcylopentene framework.