2-(4-trifluoromethylbenzoyl)benzoic acid | 1683-37-0

• 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: 2-(4-trifluoromethylbenzoyl)benzoic acid
• 英文别名: 2--benzoesaeure；2-(p-Trifluormethyl-benzoyl)-benzoesaeure；2-[4-Trifluoromethylbenzoyl]benzoic acid；2-[4-(trifluoromethyl)benzoyl]benzoic acid
• CAS: 1683-37-0
• 化学式: C₁₅H₉F₃O₃
• 分子量: 294.23
• InChiKey: WTUHFTDBRBCODT-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  439.4±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-trifluoromethylbenzoyl)benzoic acid 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 3-(4-(trifluoromethyl)phenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  钌催化的2-酰基芳基羧酸酯的对映选择性加氢/内酯化：直接获得手性3-取代的邻苯二甲酰亚胺

  摘要：

  合成子的合成：不对称氢化和随后用Ru-二膦进行原位内酯化可在温和的反应条件下将包括2-芳基芳基羧酸盐在内的一系列2-酰基芳基羧酸盐直接转化为相应的光学活性3-取代的邻苯二甲酸酯。

  DOI：

  10.1002/cctc.201700695
• 作为产物：
  描述：

  苯酐 、 4-三氟甲基苯基溴化镁 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以58 %的产率得到2-(4-trifluoromethylbenzoyl)benzoic acid
  参考文献：
  名称：

  亚甲基环丙烷的 Weinreb 酰胺定向 Umpolung 开环构建环戊[b]萘酚骨架

  摘要：

  本文公开了由 Weinreb 酰胺连接的亚甲基环丙烷和炔烃的级联环化反应，它扩展了亚甲基环丙烷的 umpolung 开环，为构建多环环戊[ b ]萘酚骨架提供了一种合成方法。在该协议中，四个碳碳键和两个碳环在不使用过渡金属的情况下形成，为构建结构相关的多环化合物提供了一种工具。

  DOI：

  10.1002/adsc.202200991

文献信息

• Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes
  作者：Hao-Zhao Wei、Yin Wei、Min Shi

  DOI：10.1039/d1cc04826k

  日期：——

  An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for

  已经揭示了一种涉及官能化亚甲基环丙烷 (MCP) 的有趣类型的反应。在这里，阴离子物质对部分极性反转的 MCP 的亲核攻击是通过用 KHMDS 处理与 MCP 相连的相邻羧酸酯和胺来实现 MCP 的 umpolung 开环来实现的。这项工作为快速构建异喹啉酮框架建立了一个操作方便的协议。
• Enantioselective Synthesis of Isoindolinone by Palladium-Catalyzed Aminoalkynylation of <i>O</i>-Phenyl Hydroxamic Ethers with Alkynes
  作者：Lei Wang、Yinqiang Wang、Shuaijie Wu、Chao-Guo Yan、Chaoshen Zhang、Junliang Zhang、Ying Han

  DOI：10.1021/jacs.3c12996

  日期：2024.2.21

  A highly efficient palladium-catalyzed asymmetric tandem aza-Heck/Sonogashira coupling reaction of O-phenyl hydroxamic ethers with terminal alkynes is described. This protocol enables versatile access to challenging chiral isoindolinone derivatives bearing a quaternary stereogenic center. The palladium-catalyzed aminoalkynylation reaction shows broad functional group tolerance and allows the straightforward

  描述了O-苯基异羟肟醚与末端炔烃的高效钯催化不对称串联 aza-Heck/Sonogashira 偶联反应。该协议能够以多种方式获得带有四元立体中心的具有挑战性的手性异吲哚啉酮衍生物。钯催化的氨基炔基化反应显示出广泛的官能团耐受性，并允许在温和条件下以高效率和优异的对映选择性直接制备异吲哚啉酮。进行 DFT 计算以揭示反应机理和对映选择性的起源。
• 5-Aryl-2,3-dihydro-5H-imidazo[2,1-a]isoindol-5-ols. Novel class of anorectic agents
  作者：Paul Aeberli、Phillip Eden、John H. Gogerty、William J. Houlihan、Chris Penberthy

  DOI：10.1021/jm00236a014

  日期：1975.2

  A series of 5-aryl-2,3-dihydro-5H-imidazo[2,1-a]isoindol-5-ols (IV), prepared by the LiA1H4 reduction of the corresponding 9b-aryl-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones (II), was evaluated for suppression of food consumption in rats. One member of this series, 5-p-chlorophenyl-2,3-dihydro-5H-imidazo[2,1-a]isoindol-5-ol (6, mazindol), was evaluated in squirrel and capuchin monkeys and found to have anorexic activity approximately equal to d-amphetamine.
• The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1
  作者：Silas Bond、Alistair G. Draffan、Jennifer E. Fenner、John Lambert、Chin Yu Lim、Bo Lin、Angela Luttick、Jeffrey P. Mitchell、Craig J. Morton、Roland H. Nearn、Vanessa Sanford、Pauline C. Stanislawski、Simon P. Tucker

  DOI：10.1016/j.bmcl.2014.11.018

  日期：2015.2

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[ 2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R-1) and benzoyl (R-2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and logD) and excellent rat pharmacokinetics (e. g., rat oral bioavailability of 89% for compound 17). (C) 2014 Elsevier Ltd. All rights reserved.
• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a008

  日期：1993.12

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.