3-(4-chlorophenyl)-3-phenylpropanoic acid | 21998-30-1

• 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-chlorophenyl)-3-phenylpropanoic acid
• CAS: 21998-30-1
• 化学式: C₁₅H₁₃ClO₂
• 分子量: 260.72
• InChiKey: CQGBVRBAVJLFOM-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±27.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-3-phenylpropanoic acid 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 1-Chloro-4-(3-chloro-1-phenylpropyl)benzene
  参考文献：
  名称：

  Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors: synthesis and structure–activity relationships

  摘要：

  Thirteen racemic benzene ring-substituted analogues of histaprodifen (8a; 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine), a novel lead for potent and selective histamine H-1-receptor agonists, have been prepared from substituted 4,4-diphenylbutyronitriles 5 via cyclization of the corresponding methyl butyrimidates 6 with 2-oxo-4-phthalimido-1-butyl acetate in liquid ammonia, followed by deprotection. Nitriles 5 were accessible by alkylation of either substituted diphenylmethanes with 3-bromopropionitrile or diethyl malonate with substituted 1-chloro-diphenylmethanes and subsequent standard reactions. The title compounds 8 displayed partial agonism on contractile H-1 receptors of the guinea-pig ileum (E-max = 2-98% relative to histamine) and, compared with the endogenous agonist, were endowed with agonist potencies of 4-92%. The meta fluorinated (gc) and meta chlorinated (8f) analogues showed the highest relative potency in this series (95% confidence Limits 85-99% and 78-102%), but did not exceed the value of the lead 8a (99-124%). Compound 8c (2-[2-[3-(3-fluorophenyl)-3-phenylpropyl]-1H-imidazol-4-yl]ethanamine) was a partial agonist at contractile H-1 receptors of the guinea-pig aorta (relative potency 154% vs. 100% for histamine) and at relaxation-mediating endothelial H-1 receptors of the rat aorta (relative potency 556% vs. 100% for histamine) and matched with the functional behaviour of 8a. Agonism observed for each compound was sensitive to blockade by the selective H-1-receptor antagonist mepyramine (pA(2) approximate to 9 (guinea-pig) and pA(2) approximate to 8 (rat aorta)). All histaprodifen analogues 8 stimulated neither histaminergic H-2/H-3, nor cholinergic M-3 receptors. They displayed only low to moderate affinity for these sites (H-2: pD'(2), < 5; H-3/M-3: pA(2) < 6). With regard to the substitution pattern on the benzene ring, there was no correlation between the histaprodifen series and the corresponding derivatives of another selective H-1-receptor agonist, viz. 2-phenylhistamine. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00105-7
• 作为产物：
  描述：

  (+/-)-p-Chlor-benzhydryl-malonsaeure 生成 3-(4-chlorophenyl)-3-phenylpropanoic acid
  参考文献：
  名称：

  取代的2,2-二苯乙胺的合成及其肾上腺皮质激素抑制活性。

  摘要：

  DOI：

  10.1021/jm00301a003

文献信息

• Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Carboxylic Acids. Synthesis of β-Quaternary Carbons Substituted Carboxylic Acids
  作者：Rui Liu、Zhenyu Yang、Yuxin Ni、Kaixuan Song、Kai Shen、Shaohui Lin、Qinmin Pan

  DOI：10.1021/acs.joc.7b01248

  日期：2017.8.4

  Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids (including β,β-disubstituted acrylic acids) was developed and optimized, which provided a mild and convenient method for the highly challenging synthesis of β-quaternary carbons substituted carboxylic acids.

  开发并优化了Pd（II）/联吡啶催化的芳基硼酸向α，β-不饱和羧酸（包括β，β-二取代的丙烯酸）的共轭加成反应，为高难度的β合成提供了温和而便捷的方法-季碳取代的羧酸。
• Boron/zinc exchange for the conjugate arylation of unsaturated Meldrum’s acid derivatives
  作者：Micaela Jardim、Lucas L. Baldassari、Maria Eduarda Contreira、Angélica V. Moro、Diogo S. Lüdtke

  DOI：10.1016/j.tet.2020.130967

  日期：2020.12

  approach for the conjugate arylation reaction of unsaturated Meldrum’s acid derivatives is reported. The reaction takes place through a Boron-Zinc exchange reaction between arylboronic acids and diethylzinc and the subsequent transfer of thus generated reactive aryl groups to the β-position of the double bond of the Meldrum’s derivatives. The compounds obtained are valuable synthetic intermediates and

  报道了不饱和梅德鲁姆酸衍生物的共轭芳基化反应方法。该反应通过芳基硼酸和二乙基锌之间的硼-锌交换反应以及随后将由此产生的反应性芳基转移至梅德鲁姆衍生物的双键的β-位进行的。所得化合物是有价值的合成中间体，并且可以产生生物活性分子，例如β，β-二取代的羧酸和酰胺。
• Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers
  作者：Faxiang Bu、Lijun Lu、Xia Hu、Shengchun Wang、Heng Zhang、Aiwen Lei

  DOI：10.1039/d0sc03708g

  日期：——

  also radical precursors. Classic transition-metal-catalyzed and photochemical decarboxylation have shown their excellent site selectivity in radical chemistry. However, electrochemical decarboxylation with a long history hasn't got enough attention in recent years. In this work, the electrochemical oxidative decarboxylation and 1,2-aryl migration of 3,3-diarylpropionic acids have been introduced to construct

  羧酸化合物是重要的化学物质，广泛存在于各种天然产物中。它们不仅是亲核试剂，还是自由基的前体。经典的过渡金属催化和光化学脱羧在自由基化学中显示出出色的位点选择性。但是，近年来，电化学脱羧历史悠久，尚未引起足够的重视。在这项工作中，已引入3,3-二芳基丙酸的电化学氧化脱羧和1,2-芳基迁移，以与醇构建C–O键。值得注意的是，这种转变无需金属催化剂和外部氧化剂即可顺利进行。
• Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids in aqueous media
  作者：Yuxin Ni、Kaixuan Song、Kai Shen、Zhenyu Yang、Rui Liu、Shaohui Lin、Qinmin Pan

  DOI：10.1016/j.tetlet.2018.02.013

  日期：2018.3

  An in-situ generated cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carboxylic acids in water was developed and optimized. For most substrates, nearly quantitative yields were given, and the products can be purified by simple washing without column chromatography. The reaction can be scaled up to 1.0 g easily with excellent yields. Also the loading of

  开发并优化了芳基硼酸到水中α，β-不饱和羧酸的阳离子Pd（II）/联吡啶催化的阳离子共轭加成反应。对于大多数底物，给出了接近定量的收率，并且可以通过不经柱色谱的简单洗涤来纯化产物。可以轻松地将反应放大至1.0 g，并具有优异的收率。同样，催化剂的载量可以以适中的产率降低到1.0mol％，并且该反应提供了温和且容易的合成β-二取代的羧酸的方法。
• Covalent organic framework supported Pd(II)‐catalyzed conjugate additions of arylboronic acids to α,β‐unsaturated carboxylic acids
  作者：Min Wen、Shujuan Lu、Chaogang Fan、Kai Shen、Shaohui Lin、Qinmin Pan

  DOI：10.1002/aoc.6263

  日期：2021.8

  A palladium(II)-coordinated covalent organic framework (Pd(II)@COF) was mechanochemically synthesized from [2,2′-bipyridine]-5,5′-diamine (Bpy) and 1,3,5-triformylphloroglucinol (Tp), which was demonstrated as a catalyst for conjugate addition of arylboronic acids to unreactive α,β-unsaturated carboxylic acids in aqueous media (water/acetone = 1:1). Modest to good yields were obtained for most substrates

  由[2,2'-联吡啶]-5,5'-二胺（Bpy）和1,3,5-三甲酰基间苯三酚（Tp）机械化学合成钯（II）配位的共价有机骨架（Pd（II）@COF） )，它被证明是芳基硼酸与非反应性 α,β-不饱和羧酸在水性介质 (水/丙酮 = 1:1) 中共轭加成的催化剂。大多数底物获得了中等至良好的产率，对催化剂可回收性的研究表明，多相催化剂在前 4 个循环中的产率大于 80%。这项研究拓宽了 COF 支持的催化的应用，并为 Pd(II) 催化提供了新的选择。