4-chlorophenylpropynoic acid butyl ester | 1449127-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chlorophenylpropynoic acid butyl ester
• 英文别名: Butyl 3-(4-chlorophenyl)propiolate；Butyl 3-(4-chlorophenyl)prop-2-ynoate
• CAS: 1449127-56-3
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: CYNHNDAVHSHSRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙炔 、 1-碘丁烷 、 二氧化碳 在 [Gd₄Cu₄I₃(CO₃)₂(IN)₉(isonicotinic acid)_0.5(DMF)(H₂O)]_n*nDMF*nH₂O 、 caesium carbonate 作用下， 80.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以74%的产率得到4-chlorophenylpropynoic acid butyl ester
  参考文献：
  名称：

  Cluster-based MOFs with accelerated chemical conversion of CO₂ through C–C bond formation

  摘要：

  我们在这里报告了两种基于团簇的MOFs，标记为 I 和 II，作为优秀的杂化催化剂，用于在1大气压和温和条件下进行CO₂和末端炔烃的羧化反应。这是MOFs材料首次催化这种类型的反应。

  DOI：

  10.1039/c7cc01136a

文献信息

• Silver tungstate: a single-component bifunctional catalyst for carboxylation of terminal alkynes with CO₂ in ambient conditions
  作者：Chun-Xiang Guo、Bing Yu、Jia-Ning Xie、Liang-Nian He

  DOI：10.1039/c4gc01638f

  日期：——

  The ligand-free carboxylation of various terminal alkynes promoted by Ag₂WO₄ was conducted at room temperature and verified with ¹³CO₂.

  各种末端炔烃的无配体羧化反应在室温下由Ag₂WO₄促进，并通过¹³CO₂验证。
• Carboxylation of terminal alkynes at ambient CO2 pressure in ethylene carbonate
  作者：Bing Yu、Zhen-Feng Diao、Chun-Xiang Guo、Chun-Lai Zhong、Liang-Nian He、Ya-Nan Zhao、Qing-Wen Song、An-Hua Liu、Jin-Quan Wang

  DOI：10.1039/c3gc40896e

  日期：——

  The CuI-catalyzed carboxylation of terminal alkynes with CO2 and alkyl halides using ethylene carbonate as the solvent under mild conditions was studied. DFT calculations reveal that the energy barrier for CO2 insertion into the sp-hybridized Cu–C bond could be reduced by employing ethylene carbonate as the solvent. Notably, the procedure was conducted under ambient CO2 pressure without any external ligands. A broad range of substrates with electron-withdrawing groups or electron-donating groups gave the corresponding products in reasonable yields.

  研究了在温和条件下，使用乙烯碳酸酯作为溶剂，通过CO2和烷基卤化物对末端炔烃进行CuI催化的羧化反应。DFT计算表明，使用乙烯碳酸酯作为溶剂能够降低 插入sp杂化Cu–C键的能量障碍。值得注意的是，整个过程是在常温常压的 条件下进行的，且没有使用任何外部配体。多种具有电子吸引基团或电子捐赠基团的底物都能以合理的产率得到相应的产物。
• Copper(I)-based ionic liquid-catalyzed carboxylation of terminal alkynes with CO2 at atmospheric pressure
  作者：Jia-Ning Xie、Bing Yu、Zhi-Hua Zhou、Hong-Chen Fu、Ning Wang、Liang-Nian He

  DOI：10.1016/j.tetlet.2015.11.028

  日期：2015.12

  An ionic liquid containing copper(I) proved to be an effective homogeneous catalyst for the carboxylation of terminal alkynes with ambient CO2. This developed procedure needs no external ligands and terminal alkynes with various groups proceeded smoothly at atmospheric CO2 pressure and room temperature. Interestingly, the ILs containing copper(I) in both the anion and the cation showed much higher

  含有铜（I）的离子液体被证明是用于末端炔烃与环境CO 2羧化的有效均相催化剂。该开发的方法不需要外部配体和带有各种基团的末端炔烃，这些炔基在大气CO 2压力和室温下可顺利进行。有趣的是，与仅以卤化高硼酸盐形式（即阴离子中的铜（I））掺入铜（I）的对应物相比，在阴离子和阳离子中均包含铜（I）的ILs表现出更高的活性。特别地，还通过NMR技术证实了末端炔烃被离子液体的活化作用。
• Copper(I)@Carbon-Catalyzed Carboxylation of Terminal Alkynes with CO₂ at Atmospheric Pressure
  作者：Bing Yu、Jia-Ning Xie、Chun-Lai Zhong、Wei Li、Liang-Nian He

  DOI：10.1021/acscatal.5b00764

  日期：2015.7.2

  Activated carbon supported CuBr was found to be an efficient catalyst for the carboxylation of terminal alkynes under atmospheric pressure of CO2 using ethylene carbonate as solvent at 80 degrees C for only 2 h, as verified with (CO2)-C-13. Various terminal alkynes could react smoothly with CO2 and organic halides under the reaction conditions to afford the corresponding carboxylic esters. In addition, the catalyst can be easily recovered and reused at least five times without significant loss of activity.