(1,2,2-trimethylcyclopent-3-en-1-yl)acetaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,2,2-trimethylcyclopent-3-en-1-yl)acetaldehyde
• 英文别名: (1,2,2-Trimethyl-3-cyclopenten-1-yl)acetaldehyde；2-(1,2,2-trimethylcyclopent-3-en-1-yl)acetaldehyde
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: AIZSHOZHOLKAGD-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：

  (1,2,2-trimethylcyclopent-3-en-1-yl)acetaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以5.11 g的产率得到2-(1,2,2-trimethylcyclopent-3-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：

  4-(2-methoxyvinyl)-3,3,4-trimethylcyclopentene 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (1,2,2-trimethylcyclopent-3-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

• Changes of Lemon Flavor Components in an Aqueous Solution during UV Irradiation
  作者：Yuko Iwanami、Hideki Tateba、Nobuko Kodama、Katsumi Kishino

  DOI：10.1021/jf960100h

  日期：1997.2.1

  A lemon flavor composed of lemon oil, water (pH 6 phosphate buffer), and ethanol, and the lemon-flavored drink were irradiated with UV light. Citral (1 and 2), which is one of the most important components expressing the typical lemon-like odor, significantly decreased with Z-E isomerization and there appeared 2-(3-methyl-2-cyclopenten-1-yl)-2-methyl (6), trans-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde (7), cis-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde (8), (1,2,2-trimethyl-3-cyclopenten-1-yl)acetaldehyde (9), alpha-campholenealdehyde (10), photocitral A (3), epiphotocitral A (4), and photocitral B (5). New compounds of aldehyde 9, 6 and 10, were newly identified as photoreaction products of citral. Limonene, terpinolene, and nonanal decreased, while p-cymene increased after UV irradiation. Other components, such as sesquiterpene hydrocarbons, citronellal, linalool, and terpineols, were only slightly changed. These results suggested that citral is a more UV-unstable component in lemon flavor and the photolysis of citral could affect other components in lemon flavor during UV irradiation.
• 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.