ethyl (4E)-5-chloropent-4-enoate | 1426946-85-1

• 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: ethyl (4E)-5-chloropent-4-enoate
• 英文别名: Ethyl (4e)-5-chloropent-4-enoate；ethyl (E)-5-chloropent-4-enoate
• CAS: 1426946-85-1
• 化学式: C₇H₁₁ClO₂
• 分子量: 162.616
• InChiKey: YNNGUMFVSJHNJV-GQCTYLIASA-N

物化性质

• 沸点：
  171.2±23.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  ethyl (4E)-5-chloropent-4-enoate 在 哌啶 、 copper(l) iodide 、 PdCl₂(PrCN)2 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 ethyl (4E,6Z)-hexadeca-4,6-dienoate
  参考文献：
  名称：

  Synthesis of (4E,6Z)-Hexadeca-4,6-dien-1-ol and Its Acetate – Components of the Sex Pheromone of Stathmopoda masinissa

  摘要：

  (4E,6Z)-Hexadeca-4,6-dien-1-ol 及其乙酸酯是通过钯催化(4E)-5-氯戊-4-烯酸乙酯（从工业上可获得的(E)-1,3-二氯丙烯和十一碳-1-炔中获得）和十一碳-1-炔的交叉偶联立体特异性合成的，它们是飞蛾 Stathmopoda masinissa 性信息素的成分。

  DOI：

  10.1007/s10600-015-1217-8
• 作为产物：
  描述：

  (E)-diethyl (but-2-en-1-yl)malonate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以76%的产率得到ethyl (4E)-5-chloropent-4-enoate
  参考文献：
  名称：

  Fe-catalyzed synthesis of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella)

  摘要：

  Starting with industrially available 1,3-dichloropropene a stereoselective process was developed for the preparation of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella) using in the key stage the Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with octylmagnesium bromide.

  DOI：

  10.1134/s1070428013050059

文献信息

• Synthesis of ethyl polychlorocyclopropanoates
  作者：Yu. G. Borisova、G. Z. Raskildina、S. S. Zlotskii

  DOI：10.1134/s1070363216080296

  日期：2016.8
• A new approach to the synthesis of ethyl (4E)-alkenoates
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070363213110078

  日期：2013.11

  A new approach to the preparation of ethyl (4E)-alkenoates was developed on the basis of Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with the Grignard reagents. The starting ethyl (4E)-5-chloropent-4-enoate was obtained by alkylation of malonic ester of (E)-1,3-dichloropropene followed by decarbethoxylation.
• Synthesis of ethyl (4E)-tridec-4-ene-6-ynoate
  作者：A. Sh. Sunagatullina、R. N. Shakhmaev、V. V. Zorin

  DOI：10.1134/s1070363213010313

  日期：2013.1

  Various cross-coupling reactions based on vinyl halides, which proceed with the retention of the double bond configuration (Negishi, Sonogashira, Suzuki, Stille, Heck reactions), are widely used to create the carbon-carbon bonds in the synthesis of the practically useful unsaturated compounds [1–5]. Previously, we have synthesized the stereochemically pure chlorovinyl-derived malonic esters, which
• Synthesis of (4E,6Z)-Hexadeca-4,6-dien-1-ol and Its Acetate – Components of the Sex Pheromone of Stathmopoda masinissa
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、N. V. Emyshaeva、V. V. Zorin

  DOI：10.1007/s10600-015-1217-8

  日期：2015.1

  (4E,6Z)-Hexadeca-4,6-dien-1-ol and its acetate, components of the sex pheromone of the moth Stathmopoda masinissa, were synthesized stereospecifically via Pd-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate, which was obtained from industrially available (E)-1,3-dichloropropene, and undec-1-yne.

  (4E,6Z)-Hexadeca-4,6-dien-1-ol 及其乙酸酯是通过钯催化(4E)-5-氯戊-4-烯酸乙酯（从工业上可获得的(E)-1,3-二氯丙烯和十一碳-1-炔中获得）和十一碳-1-炔的交叉偶联立体特异性合成的，它们是飞蛾 Stathmopoda masinissa 性信息素的成分。
• Fe-catalyzed synthesis of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella)
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070428013050059

  日期：2013.5

  Starting with industrially available 1,3-dichloropropene a stereoselective process was developed for the preparation of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella) using in the key stage the Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with octylmagnesium bromide.