(Z)-3-(2-methoxy-vinyl)-3,4,4-trimethyl-cyclopentene | 1187086-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-(2-methoxy-vinyl)-3,4,4-trimethyl-cyclopentene
• 英文别名: 3-[(Z)-2-methoxyethenyl]-3,4,4-trimethylcyclopentene
• CAS: 1187086-94-7
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: CTJMVFWPXKZBJZ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-methoxy-vinyl)-3,4,4-trimethyl-cyclopentene 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2-(1,5,5-trimethylcyclopent-2-en-1-yl)acetaldehyde
  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-trimethylcyclopent-2-ene-1-carbaldehyde 、 甲氧基甲基三苯基氯化膦 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以4.81 g的产率得到(Z)-3-(2-methoxy-vinyl)-3,4,4-trimethyl-cyclopentene
  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.