4-(1,3-Dimethyl-4-oxo-cyclopent-2-enyl)-2-methylene-butyraldehyde | 313254-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1,3-Dimethyl-4-oxo-cyclopent-2-enyl)-2-methylene-butyraldehyde
• 英文别名: 4-(1,3-Dimethyl-4-oxocyclopent-2-en-1-yl)-2-methylidenebutanal
• CAS: 313254-72-7
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BCSOZQIBVUTMGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1,3-Dimethyl-4-oxo-cyclopent-2-enyl)-2-methylene-butyraldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.5h， 生成 methyl 2-[2-(1,3-dimethyl-4-oxo-2-cyclopent-1-yl)ethyl]propenoate
  参考文献：
  名称：

  Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

  摘要：

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00735-3
• 作为产物：
  描述：

  3-Dimethoxymethyl-but-3-en-1-ol 在 咪唑 、 碘 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 7.75h， 生成 4-(1,3-Dimethyl-4-oxo-cyclopent-2-enyl)-2-methylene-butyraldehyde
  参考文献：
  名称：

  Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

  摘要：

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00735-3

文献信息

• Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas
  作者：Shigefumi Kuwahara、Shiharu Hamade、Walter Soares Leal、Jiro Ishikawa、Osamu Kodama

  DOI：10.1016/s0040-4020(00)00735-3

  日期：2000.10

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.