2-[(E/Z)-2-(3-nitrophenyl)-vinyl]-benzoic acid | 915034-80-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[(E/Z)-2-(3-nitrophenyl)-vinyl]-benzoic acid
• 英文别名: (E/Z)-3'-nitrostilbene-2-carboxylic acid；2-[2-(3-Nitrophenyl)ethenyl]benzoic acid
• CAS: 915034-80-9
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: XKBWHSSSMBVXJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  468.5±34.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E/Z)-2-(3-nitrophenyl)-vinyl]-benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 10.0h， 生成 2-[2-(3-aminophenyl)-ethyl]-benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Phenylamino-Substituted 6,11-Dihydro-dibenzo[b,e]oxepin-11-ones and Dibenzo[a,d]cycloheptan-5-ones:  Novel p38 MAP Kinase Inhibitors

  摘要：

  The pathogenesis of chronic inflammatory diseases is promoted by various pro-inflammatory cytokines. p38 MAP kinase seems to be a valid target as it controls proinflammatory cytokine levels on both transcriptional and translational levels. Starting from benzophenone-type inhibitors, a rigidisation strategy lead to 3-amino-6,11-dihydro-dibenzo[b,e]thiepin-11-one, phenylamino-substituted 6,11-dihydro-dibenzo[b,e]oxepin-11-ones, and dibenzo[a,d]cyclohepten-5-ones. Synthesis, p38 inhibition, and CYP-inhibition of selected compounds are described.

  DOI：

  10.1021/jm061072p
• 作为产物：
  描述：

  2-溴甲基苯甲酸甲酯 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 17.0h， 生成 2-[(E/Z)-2-(3-nitrophenyl)-vinyl]-benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Phenylamino-Substituted 6,11-Dihydro-dibenzo[b,e]oxepin-11-ones and Dibenzo[a,d]cycloheptan-5-ones:  Novel p38 MAP Kinase Inhibitors

  摘要：

  The pathogenesis of chronic inflammatory diseases is promoted by various pro-inflammatory cytokines. p38 MAP kinase seems to be a valid target as it controls proinflammatory cytokine levels on both transcriptional and translational levels. Starting from benzophenone-type inhibitors, a rigidisation strategy lead to 3-amino-6,11-dihydro-dibenzo[b,e]thiepin-11-one, phenylamino-substituted 6,11-dihydro-dibenzo[b,e]oxepin-11-ones, and dibenzo[a,d]cyclohepten-5-ones. Synthesis, p38 inhibition, and CYP-inhibition of selected compounds are described.

  DOI：

  10.1021/jm061072p

文献信息

• Catalyst-Controlled Regio- and Stereoselective Bromolactonization with Chiral Bifunctional Sulfides
  作者：Ayano Tsuchihashi、Seiji Shirakawa

  DOI：10.1055/s-0037-1610716

  日期：2019.9

  Highly regioselective 5-exo bromolactonizations of stilbene-type carboxylic acids bearing electron-withdrawing substituents are achieved for the first time via the use of chiral bifunctional sulfide catalysts possessing a urea moiety. The chiral phthalide products are obtained in moderate to good enantioselectivities as the result of 5-exo cyclizations.

  通过使用具有尿素部分的手性双功能硫化物催化剂，首次实现了具有吸电子取代基的二苯乙烯型羧酸的高度区域选择性 5-外溴内酯化。作为 5-exo 环化的结果，手性苯酞产物以中等至良好的对映选择性获得。
• Trifluoroacetic acid catalyzed highly regioselective bromocyclization of styrene-type carboxylic acid
  作者：Tao Chen、Ying-Yeung Yeung

  DOI：10.1039/c6ob00756b

  日期：——

  A trifluoroacetic acid catalyzed highly 6-endo regioselective bromocyclization of styrene-type carboxylic acid has been developed. The resulting 3,4-dihydroisocoumarines are valuable building blocks in organic synthesis.

  已经开发了三氟乙酸催化苯乙烯型羧酸的高度6-内位区域选择性溴环化。所得的3,4-二氢异香豆素是有机合成中的重要组成部分。
• WO2006/120010
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, Synthesis, and Biological Evaluation of Phenylamino-Substituted 6,11-Dihydro-dibenzo[<i>b</i>,<i>e</i>]oxepin-11-ones and Dibenzo[<i>a</i>,<i>d</i>]cycloheptan-5-ones:  Novel p38 MAP Kinase Inhibitors
  作者：Stefan A. Laufer、Gabriele M. Ahrens、Solveigh C. Karcher、Jörg S. Hering、Raimund Niess

  DOI：10.1021/jm061072p

  日期：2006.12.1

  The pathogenesis of chronic inflammatory diseases is promoted by various pro-inflammatory cytokines. p38 MAP kinase seems to be a valid target as it controls proinflammatory cytokine levels on both transcriptional and translational levels. Starting from benzophenone-type inhibitors, a rigidisation strategy lead to 3-amino-6,11-dihydro-dibenzo[b,e]thiepin-11-one, phenylamino-substituted 6,11-dihydro-dibenzo[b,e]oxepin-11-ones, and dibenzo[a,d]cyclohepten-5-ones. Synthesis, p38 inhibition, and CYP-inhibition of selected compounds are described.