(2Z,4E)-ethyl 5-cyclohexylpenta-2,4-dienoate | 144782-99-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z,4E)-ethyl 5-cyclohexylpenta-2,4-dienoate
• 英文别名: ethyl (2Z,4E)-5-cyclohexylpenta-2,4-dienoate
• CAS: 144782-99-0
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: GGUMOYCHYYNTDK-QZTBCQRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (2Z,4E)-ethyl 5-cyclohexylpenta-2,4-dienoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以78%的产率得到(2Z,4E)-5-Cyclohexylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Key structural features of cis-cinnamic acid as an allelochemical

  摘要：

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.08.001
• 作为产物：
  描述：

  (E)-3-cyclohexylpropenal 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.25h， 以64%的产率得到(2Z,4E)-ethyl 5-cyclohexylpenta-2,4-dienoate
  参考文献：
  名称：

  Key structural features of cis-cinnamic acid as an allelochemical

  摘要：

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.08.001

文献信息

• Key structural features of cis-cinnamic acid as an allelochemical
  作者：Masato Abe、Keisuke Nishikawa、Hiroshi Fukuda、Kazunari Nakanishi、Yuta Tazawa、Tomoya Taniguchi、So-young Park、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2012.08.001

  日期：2012.12

  1-O-cis-cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the as-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclo-hexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated. (c) 2012 Elsevier Ltd. All rights reserved.