2-(1,5,5-trimethylcyclopent-2-en-1-yl)acetaldehyde | 1160363-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,5,5-trimethylcyclopent-2-en-1-yl)acetaldehyde
• 英文别名: (1,5,5-trimethyl-cyclopent-2-enyl)-acetaldehyde
• CAS: 1160363-73-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: UNYBNTRWEWZXSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1,5,5-trimethylcyclopent-2-en-1-yl)acetaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以0.351 g的产率得到2-(1,5,5-trimethylcyclopent-2-en-1-yl)ethanol
  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：

  3-(2-methoxyvinyl)-3,4,4-trimethylcyclopentene 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2-(1,5,5-trimethylcyclopent-2-en-1-yl)acetaldehyde
  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

文献信息

• 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.