N-(2-chlorophenyl)-3-phenylacrylamide | 73108-79-9

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(2-chlorophenyl)-3-phenylacrylamide
• 英文别名: N-(2-chloro-phenyl)-3-phenylacrylamide；N-(o-Chlor-phenyl)-cinnamamid；N-(2-chlorophenyl)-3-phenylprop-2-enamide
• CAS: 73108-79-9
• 化学式: C₁₅H₁₂ClNO
• mdl: MFCD00157758
• 分子量: 257.719
• InChiKey: FKLXMLNUDVRAJG-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  453.2±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P264,P270,P273,P301+P312,P330,P391,P501
• 危险性描述：
  H302,H411
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N-(2-chlorophenyl)-3-phenylacrylamide 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以40%的产率得到8-chloro-4-phenyl-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  The triflic acid-mediated cyclisation of N-benzylcinnamanilides

  摘要：

  N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2,4-dihydro-1H-quinolin-2-ones and 2,5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho-substituted anilides, N-debenzylation also occurs to give 4-aryl-2,4-dihydro-1H-quinoline-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.075
• 作为产物：
  描述：

  2,3-二溴-3-苯基丙酸 在 吡啶 、 氯化亚砜 作用下， 以 甲醇 、 苯 为溶剂， 反应 28.0h， 生成 N-(2-chlorophenyl)-3-phenylacrylamide
  参考文献：
  名称：

  PHOTOCHEMICAL DEBROMINATION OF vic-DIBROMIDES

  摘要：

  Photochemical debromination of dibromohydro cinnamamides gave the carbon-carbon double bond compounds.

  DOI：

  10.1081/scc-100105886

文献信息

• Synthesis and structure–activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao Tang、Yu-Ping Tang、Wei Li、Lian Yin、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1016/j.bmcl.2013.01.027

  日期：2013.3

  Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure–activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of

  合成了四个系列的酰胺，并通过使用荧光底物测定法与人重组MMP-1，MMP-2和MMP-9进行测量，化合物3f对MMP-2，MMP-9表现出相当大的抑制活性，并且选择性优于MMP-1。初步的结构-活性关系分析表明，在氨基苯基对位具有供电子基团的咖啡酰胺比具有吸电子基团的酰胺具有更好的抑制活性和选择性，并且在咖啡酰基中相邻的二羟基的存在非常多。对于MMP-2和MMP-9抑制活性很重要。
• Regioselective copper catalyzed synthesis of benzimidazoles and azabenzimidazoles
  申请人：ALONSO Jorge

  公开号：US20100261909A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for the regioselective synthesis of compounds of the formula I, wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4, Q and J have the meanings indicated in the claims. The present invention provides a direct copper catalyzed regioselective process to a wide variety of unsymmetrical, multifunctional N-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N-substituted amides.

  本发明涉及一种配合物I的区域选择性合成方法，其中R0; R1; R2; R3; R4; R5; A1; A2; A3; A4，Q和J具有声明中指示的含义。本发明提供了一种直接铜催化的区域选择性方法，可从2-卤代硝基芳烃和N-取代酰胺出发，合成广泛的非对称、多功能N-取代苯并咪唑或氮杂苯并咪唑配合物I。
• Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines
  作者：Andrea Angeli、Elena Trallori、Fabrizio Carta、Lorenzo Di Cesare Mannelli、Carla Ghelardini、Claudiu T. Supuran

  DOI：10.1021/acsmedchemlett.8b00362

  日期：2018.9.13

  We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.
• WO2009/413
  申请人：——

  公开号：——

  公开（公告）日：——
• The triflic acid-mediated cyclisation of N-benzylcinnamanilides
  作者：Frank D. King、Stephen Caddick

  DOI：10.1016/j.tet.2013.07.075

  日期：2013.10

  N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2,4-dihydro-1H-quinolin-2-ones and 2,5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho-substituted anilides, N-debenzylation also occurs to give 4-aryl-2,4-dihydro-1H-quinoline-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.