undec-2-en-4-ynoic acid methyl ester | 109384-42-1

• 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: undec-2-en-4-ynoic acid methyl ester
• 英文别名: methyl (E)-undec-2-en-4-ynoate
• CAS: 109384-42-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: DIPWNDOHNWNBGC-ZHACJKMWSA-N

物化性质

• 沸点：
  74 °C(Press: 0.02 Torr)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  undec-2-en-4-ynoic acid methyl ester 在 bis(1,5-cyclooctadiene)nickel (0) 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以60%的产率得到(E)-3-[2,3,6-trihexyl-4,5-bis{(E)-2-methoxycarbonylvinyl}phenyl]acrylic acid methyl ester
  参考文献：
  名称：

  Highly Regioselective Cyclotrimerization of 1-Perfluoroalkylenynes Catalyzed by Nickel

  摘要：

  We report the highly regioselective cyclotrimerization of the 1-perfluoroalkylenynes in the presence of Ni(PPh3)(4). The substituent effects on the reactivity of the enynes were investigated. We also succeeded in the nickel-catalyzed cocyclization of the 1-perfluoroalkylenynes with (trimethylsilyl)acetylene. The possible structures of the intermediates of the cyclotrimerization and the reasons for the observed high regioselectivity were discussed.

  DOI：

  10.1021/jo0056242
• 作为产物：
  描述：

  1-iodooct-1-yne 、 丙烯酸甲酯（MA） 在 palladium diacetate 四丁基氯化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到undec-2-en-4-ynoic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Vinylation of Acetylenic Iodides under Solid-Liquid Please-Transfer Conditions

  摘要：

  甲基(E)-炔酯和(E)-烯酮可以通过在固-液相转移条件下（碳酸钾或碳酸钠/四丁基氯化铵），采用钯催化的乙烯基化反应，从1-碘-1-炔烃制备，产率良好。

  DOI：

  10.1055/s-1987-27851

文献信息

• Hydroxyapatite-Supported Palladium-Catalyzed Efficient Synthesis of (<i>E</i>)-2-Alkene-4-ynecarboxylic Esters. Intense Fluorescene Emission of Selected Compounds
  作者：Brindaban C. Ranu、Laksmikanta Adak、Kalicharan Chattopadhyay

  DOI：10.1021/jo800209z

  日期：2008.7.1

  A simple procedure for the synthesis of substituted (E)-2-alkene-4-ynecarboxylic esters has been achieved using hydroxyapatite-supported palladium as efficient catalyst surface. The catalyst is recycled, and the turnover number (TON) based on Pd is 16000. A naphthyl-substituted derivative gives very intense fluorescence emission.
• JEFFERY T., SYNTHESIS,(1987) N 1, 70-71
  作者：JEFFERY T.

  DOI：——

  日期：——
• Palladium-Catalyzed Vinylation of Acetylenic Iodides under Solid-Liquid Please-Transfer Conditions
  作者：Tuyet Jeffery

  DOI：10.1055/s-1987-27851

  日期：——

  Methyl (E)-enynoates and (E)-enyones can be obtained in fair yields by Pd-catalyzed vinylation of 1-iodo-1-alkynes under solid-liquid phase-transfer conditions (potassium carbonate or sodium carbonate/ tetrabutylammonium chloride).

  甲基(E)-炔酯和(E)-烯酮可以通过在固-液相转移条件下（碳酸钾或碳酸钠/四丁基氯化铵），采用钯催化的乙烯基化反应，从1-碘-1-炔烃制备，产率良好。
• Highly Regioselective Cyclotrimerization of 1-Perfluoroalkylenynes Catalyzed by Nickel
  作者：Shinichi Saito、Taishi Kawasaki、Norie Tsuboya、Yoshinori Yamamoto

  DOI：10.1021/jo0056242

  日期：2001.2.1

  We report the highly regioselective cyclotrimerization of the 1-perfluoroalkylenynes in the presence of Ni(PPh3)(4). The substituent effects on the reactivity of the enynes were investigated. We also succeeded in the nickel-catalyzed cocyclization of the 1-perfluoroalkylenynes with (trimethylsilyl)acetylene. The possible structures of the intermediates of the cyclotrimerization and the reasons for the observed high regioselectivity were discussed.