3-(4-(methoxycarbonyl)phenyl)propiolic acid | 1357155-90-8

• 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: 3-(4-(methoxycarbonyl)phenyl)propiolic acid
• 英文别名: 3-[4-(Methoxycarbonyl)phenyl]prop-2-ynoic acid；3-(4-methoxycarbonylphenyl)prop-2-ynoic acid
• CAS: 1357155-90-8
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: LQGZAFUGYHMCEG-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±34.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(methoxycarbonyl)phenyl)propiolic acid 在 copper(l) iodide 、 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以97%的产率得到dimethyl 4,4'-(buta-1,3-diyne-1,4-diyl)dibenzoate
  参考文献：
  名称：

  Synthesis of 1,4-diarylsubstituted 1,3-diynes through ligand-free copper-catalyzed oxidative decarboxylative homocoupling of aryl propiolic acids

  摘要：

  An efficient method of ligand-free Cu-catalyzed oxidative decarboxylative homocoupling of aryl propiolic acids was developed. When CuI was employed as the catalyst and 12 as the oxidant, the decarboxylative homocoupling reaction for C-sp-C-sp bond formation in DMSO underwent smoothly to afford the corresponding 1,4-disubstituted 1,3-dialkynes in good to excellent yields without any organic ligands. This catalytic system was applicable to aryl propiolic acids bearing different steric, electronic, and functional groups. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.022
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3-(4-(methoxycarbonyl)phenyl)propiolic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of phenyl-substituted coumarins with anti-tubercular activity that target FadD32

  摘要：

  In an effort to develop new and potent agents for therapy against tuberculosis, a high-throughput screen was performed against Mycobacterium tuberculosis strain H37Rv. Two 6-aryl-5,7-dimethyl-4-phenylcoumarin compounds 1a and 1b were found with modest activity. A series of coumarin derivatives were synthesized to improve potency and to investigate the structure-activity relationship of the series. Among them, compounds 1o and 2d showed improved activity with IC90 of 2 mu M and 0.5 mu M, respectively. Further optimization provided compound 3b with better physiochemical properties with IC90 0.4 mu M which had activity in a mouse model of infection. The role of the conformation of the 4- and 6-aryl substituents is also described. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.035

文献信息

• Metal-Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones
  作者：Aravindan Jayaraman、Eunjeong Cho、Francis Mariaraj Irudayanathan、Jimin Kim、Sunwoo Lee

  DOI：10.1002/adsc.201701116

  日期：2018.1.4

  arylpropiolic acids and trichloroisocyanuric acid (TCCA). The reaction was performed in the presence of water at room temperature, and the desired products were obtained in good yields. The reaction showed good functional group tolerance towards halide, cyano, nitro, ketone, ester and aldehyde groups. In addition, the 2,2,2‐trichloroacetophenone derivatives were readily transformed into esters, amides,

  2,2,2-三氯苯乙酮衍生物是通过芳基丙酸和三氯异氰尿酸（TCCA）的脱羧三氯化反应合成的。该反应在室温下在水的存在下进行，并且以良好的产率获得了所需的产物。反应显示出对卤化物，氰基，硝基，酮，酯和醛基的良好的官能团耐受性。此外，2,2,2-三氯苯乙酮衍生物很容易转化为酯，酰胺和酰肼。基于H 2 18 O（水18 O）的实验，我们提出了阳离子反应途径作为机理，并提出了两种不同的途径来生产芳基和烷基取代的丙酸。
• Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles
  作者：Kuppusamy Bharathimohan、Thanasekaran Ponpandian、A Jafar Ahamed、Nattamai Bhuvanesh

  DOI：10.3762/bjoc.10.321

  日期：——

  Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.

  在这里，我们描述了一种一锅法合成新型多环三唑衍生物系列的方法。过渡金属催化的脱羧CuAAC和脱氢交叉偶联反应结合在一个烧瓶中，获得了相应三唑的良好产率（高达97%）。这种方法更方便地以简单方式生产复杂的多环分子。
• Ni/Cu-Catalyzed Decarboxylative Addition of Alkynoic Acids to Terminal Alkynes for the Synthesis of <i>gem</i>-1,3-Enynes
  作者：Sehyeon Han、Han-Sung Kim、Maosheng Zhang、Yuanzhi Xia、Sunwoo Lee

  DOI：10.1021/acs.orglett.9b01625

  日期：2019.7.19

  The synthesis of gem-1,3-enynes via Ni/Cu-catalyzed decarboxylative addition of alkynoic acids to terminal alkynes has been developed. It was found that the decarboxylation of an alkynoic acid led predominantly to gem-1,3-enynes instead of 1,3-diynes, which have been known to be formed through the coupling of terminal alkynes. A variety of gem-1,3-enynes were obtained in good yields. This catalytic

  的合成宝石通过镍/铜催化的脱羧加入alkynoic酸以末端炔-1,3-烯炔已经研制成功。已经发现，一个alkynoic脱羧主要导致宝石-1,3-烯炔，而不是1,3-二炔，它已经知道通过末端炔烃的联接而形成。以高收率获得了多种宝石-1，3-烯炔。该催化体系表现出优异的区域选择性和高官能团耐受性。
• Decarboxylative Tribromination for the Selective Synthesis of Tribromomethyl Ketone and Tribromovinyl Derivatives
  作者：Aravindan Jayaraman、Eunjeong Cho、Jimin Kim、Sunwoo Lee

  DOI：10.1002/adsc.201800851

  日期：2018.10.18

  Tribromomethyl ketone and tribromovinyl derivatives were selectively prepared from the decarboxylative tribromination. The reaction between propiolic acid derivatives and dibromoisocyanuric acid (DBCA)/H2O afforded predominantly a tribromomethyl ketone derivative in the presence of AgOAc (10 mol%). When the same reaction was conducted with 2,2,6,6‐tetramethyl‐1‐piperidinyloxy (TEMPO) instead of AgOAc

  由脱羧三溴化作用选择性地制备三溴甲基酮和三溴乙烯基衍生物。在AgOAc（10mol％）存在下，丙酸衍生物与二溴异氰尿酸（DBCA）/ H 2 O之间的反应主要得到三溴甲基酮衍生物。当用2,2,6,6-四甲基-1-哌啶基氧基（TEMPO）代替AgOAc进行相同的反应时，仅以高收率形成了三溴乙烯基衍生物。发现乙炔基溴是中间体。
• Palladium-Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids
  作者：Jinil Hwang、Kyungho Park、Juseok Choe、Hongkeun Min、Kwang Ho Song、Sunwoo Lee

  DOI：10.1021/jo5003032

  日期：2014.4.4

  A trifluoroethylation of alkynes through a palladium-catalyzed decarboxylative coupling reaction was developed. When alkynyl carboxylic acids and ICH2CF3 were allowed to react with [Pd(η3-allyl)Cl]2/XantPhos and Cs2CO3 in N,N-dimethylformamide (DMF) at 80 °C for 1 h, the desired products were formed in good yields. This catalytic system showed high functional group tolerance.

  通过钯催化的脱羧偶联反应，开发了炔烃的三氟乙基化反应。当炔基羧酸和ICH 2 CF 3被允许通过[加入Pd（η反应3 -烯丙基）CL] 2 / XANTPHOS和Cs 2 CO 3在Ñ，Ñ在80二甲基甲酰胺（DMF）℃下反应1个小时后，将所需产物以高收率形成。该催化体系显示出高的官能团耐受性。