N-(4-chlorophenyl)cinnamamide | 53691-91-1

• 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-(4-chlorophenyl)cinnamamide
• 英文别名: N-(4-chlorophenyl)-3-phenylacrylamide；N-(4-chlorophenyl)-3-phenylprop-2-enamide
• CAS: 53691-91-1
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: LSOIYQMAEOVIGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)cinnamamide 在 aluminum (III) chloride 、 三氯氧磷 作用下， 反应 22.5h， 生成 2,6-二氯喹啉
  参考文献：
  名称：

  6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

  摘要：

  Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6 -substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.

  DOI：

  10.1021/acsmedchemlett.7b00196
• 作为产物：
  描述：

  3-(4-氯苯基)-1-苯基丙-2-炔-1-醇 在 三甲基氯硅烷 、 叠氮基三甲基硅烷 、 水 、 溶剂黄146 作用下， 以32%的产率得到N-(4-chlorophenyl)cinnamamide
  参考文献：
  名称：

  TMSCl介导的丙三醇与叠氮化三甲硅烷基的碳键裂解和碳氮键形成，合成α，β-不饱和酰胺

  摘要：

  开发了一种新的高效方法，该方法利用TMSC1作为酸促进剂，由易于制备的炔丙醇和TMSN 3合成α，β-不饱和酰胺。以中等至优异的产率制备了多种α，β-不饱和酰胺。机理研究表明，这种转化涉及TMSC1介导的烯丙基叠氮化物中间体的形成，CC键的裂解和CN键的形成。重要的是，该反应显示出良好的官能团相容性和高区域选择性，并且反应时间相对较短且试剂便宜。

  DOI：

  10.1021/jo5013948

文献信息

• Sulfated tungstate: a highly efficient catalyst for transamidation of carboxamides with amines
  作者：Sagar P. Pathare、Ashish Kumar H. Jain、Krishnacharya G. Akamanchi

  DOI：10.1039/c3ra00127j

  日期：——

  An environmentally benign protocol for the transamidation of carboxamides with amines using sulfated tungstate, as a heterogeneous catalyst, has been developed. The method has been successfully applied to the synthesis of a wide range of aromatic and aliphatic amides and phthalimides. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst

  已经开发出一种环境友好的方案，用于使用硫酸化钨酸盐作为非均相催化剂将羧酰胺与胺进行氨基转移。该方法已成功应用于多种芳族和脂族酰胺和邻苯二甲酰亚胺的合成。高效的转化，温和的反应条件，容易的产物分离和催化剂的潜在可重复使用性是吸引人的特征。
• Oxindole synthesis by palladium-catalysed aromatic C–H alkenylation
  作者：Satoshi Ueda、Takahiro Okada、Hideko Nagasawa

  DOI：10.1039/b926560k

  日期：——

  A strategy involving palladium-catalysed aromatic C-H functionalisation/intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl(2)MeCN(2) and AgOCOCF(3), a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield.

  涉及钯催化的芳族CH官能化/分子内烯基化的策略提供了3-亚烷基亚氧吲哚的方便和直接的合成。在5 mol％的PdCl（2）MeCN（2）和AgOCOCF（3）的存在下，各种各样的N-肉桂酰基苯胺以中等至良好的收率得到3-亚烷基亚甲基吲哚。
• Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes
  作者：Jin-Bao Peng、Hui-Qing Geng、Da Li、Xinxin Qi、Jun Ying、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.8b02109

  日期：2018.8.17

  A procedure on palladium-catalyzed selective aminocarbonylation of styrenes with nitroarenes for the synthesis of α,β-unsaturated amides has been developed. A range of substituted α,β-unsaturated amides were synthesized in moderate to good yields. Interestingly, nitroarenes act as both a nitrogen source and oxidant, and Mo(CO)6 acts as a solid CO source and reductant in this catalytic system.

  已经开发了钯与硝基芳烃催化的苯乙烯选择性氨基羰基化合成α，β-不饱和酰胺的方法。以中等至良好的产率合成了一系列取代的α，β-不饱和酰胺。有趣的是，在该催化体系中，硝基芳烃既充当氮源又充当氧化剂，而Mo（CO）6充当固态CO源和还原剂。
• Direct Amidation of Carboxylic Acids with Nitroarenes
  作者：Shao-Peng Wang、Chi Wai Cheung、Jun-An Ma

  DOI：10.1021/acs.joc.9b02068

  日期：2019.11.1

  N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium

  N-芳基酰胺是药物和农业化学中重要的一类化合物。对N-芳基酰胺的快速且低成本的合成仍然有很高的需求。本文中，我们公开了一种操作简单的方法，可直接从容易获得的硝基芳烃和羧酸作为偶联底物直接获得N-芳基酰胺。该方法涉及将羧酸原位活化为酰氧基phosph盐以进行一锅酰胺化，而无需分离相应的合成中间体。此外，制备和后处理的简便性允许快速有效地合成多种N-芳基酰胺，包括几种基于酰胺的类药物和农用化学分子。
• Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon–Carbon Bonds with Chlorine on Demand
  作者：Feng Liu、Na Wu、Xu Cheng

  DOI：10.1021/acs.orglett.1c00704

  日期：2021.4.16

  electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

  用氯进行氯化是直接的，高反应性的，并且用途广泛，但是有很大的局限性。在这封信中，我们介绍了一种可以结合电化学转化效率和氯的高反应活性的方案。通过使用Cl 3 CCN作为氯化物源，最多提供三个氯原子，该反应可按需就地生成和消耗氯，以实现芳族化合物和电有效链烯烃的氯化。