3-phenyl-3-m-methylphenylpropionic acid | 4073-49-8

• 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-phenyl-3-m-methylphenylpropionic acid
• 英文别名: (+/-)-3-(m-Methyl-phenyl)-3-phenyl-propionsaeure；3-phenyl-3-m-tolyl-propionic acid；β-Phenyl-β-m-tolyl-propionsaeure；3-Phenyl-3-m-tolyl-propionsaeure；3-(3-Methylphenyl)-3-phenyl-propionic acid；β-m-Tolyl-hydrozimtsaeure；3-(3-Methylphenyl)-3-phenylpropanoic acid
• CAS: 4073-49-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: UOPMKNZFFSPUIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-m-methylphenylpropionic 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-(3-Chloro-1-phenyl-propyl)-3-methyl-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：

  3-methyl-benzhydryl chloride 在 氢氧化钾 、 sodium hydride 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.17h， 生成 3-phenyl-3-m-methylphenylpropionic acid
  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

文献信息

• Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
  作者：Yan Huang、Jing Hou、Le-Wu Zhan、Qian Zhang、Wan-Ying Tang、Bin-Dong Li

  DOI：10.1021/acscatal.1c04684

  日期：2021.12.17

  reagent, a wide range of alkenes can be converted into acid products via a carboxyl group transfer strategy in an additive-free fashion. Mechanistic studies revealed that radical anion species (CO2•– and carbon radical anions derived from the reduction of alkenes) are key intermediates of the transformation. This method has the advantages of high catalytic efficiency and a simple catalytic system, which

  开发了用于羧化的甲酸盐的光氧化还原活化模式。使用甲酸盐作为还原剂、羰基源和氢原子转移试剂，可以通过羧基转移策略以无添加剂的方式将各种烯烃转化为酸性产物。机理研究表明自由基阴离子物质（CO 2 •–和来自烯烃还原的碳自由基阴离子）是转化的关键中间体。该方法具有催化效率高、催化体系简单等优点，有望成为一种有前景的工业应用策略。
• Imidazolyl-substituierte Phenylpropion- und Zimtsäurederivate
  申请人：BAYER AG

  公开号：EP0578002A1

  公开（公告）日：1994-01-12

  Imidazolyl-substituierte Phenylpropion- und -zimtsäurederivate werden hergestellt, indem man entsprechende Benzylverbindungen mit Imidazolen umsetzt und gegebenenfalls die Substituenten variiert. Die Imidazolyl-substituierten Phenylpropion- und -zimtsäurederivate können als Wirkstoffe in Arzneimitteln, insbesondere bei der Behandlung von arterieller Hypertonie und Atherosklerose verwendet werden.

  咪唑基取代的苯丙酸和肉桂酸衍生物是通过相应的苄基化合物与咪唑反应并在必要时改变取代基来制备的。咪唑基取代的苯丙酸和肉桂酸衍生物可用作药物的活性成分，特别是用于治疗动脉高血压和动脉粥样硬化。
• 一种光催化烯烃类化合物与二氧化碳发生反马氏氢羧化反应的方法
  申请人：中国科学院理化技术研究所

  公开号：CN115197036A

  公开（公告）日：2022-10-18

  本发明公开一种光催化烯烃类化合物与二氧化碳发生反马氏氢羧化反应的方法，包括以下步骤：1)将光催化剂和电子牺牲体加入至溶剂中，得溶液A；2)将烯烃类化合物加入至溶液A中，得溶液B；3)在二氧化碳气氛中，用光源照射溶液B，烯烃类化合物与二氧化碳发生反马氏氢羧化反应。本发明首次通过光驱动的量子点催化实现了烯烃类化合物与二氧化碳的反马氏选择性的氢羧化反应。且该方法过程简单、条件温和、不需要高温高压、反应物范围广、光催化剂可循环利用，可以在克级规模反应制备反马氏氢羧化产物。
• v. Braun; Manz; Reinsch, Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 288
  作者：v. Braun、Manz、Reinsch

  DOI：——

  日期：——
• Synthesis and adrenocortical-inhibiting activity of substituted 2,2-diphenethylamines
  作者：William A. Zuccarello、Benjamin Blank、Gertrude J. Frishmuth、Suzanne R. Cohen、Daniel Scaricaciottoli、Franklin F. Owings

  DOI：10.1021/jm00301a003

  日期：1969.1