1,5,5-trimethylcyclopent-2-enecarboxylic acid methyl ester | 861317-32-0

• 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: 1,5,5-trimethylcyclopent-2-enecarboxylic acid methyl ester
• 英文别名: Methyl 1,5,5-trimethylcyclopent-2-ene-1-carboxylate
• CAS: 861317-32-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: ZDFSBPIKZDXFHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,5,5-trimethyl-2-trifluoromethanesulfonyloxycyclopent-2-enecarboxylic acid methyl ester 在 甲酸 、 三正丁胺 、 palladium diacetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以82%的产率得到1,5,5-trimethylcyclopent-2-enecarboxylic acid methyl ester
  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

• 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.