N-(β-Benzoylvinyl)-m-chloranilin | 37418-66-9

• 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: N-(β-Benzoylvinyl)-m-chloranilin
• 英文别名: 3-(3-Chloroanilino)-1-phenylprop-2-en-1-one
• CAS: 37418-66-9
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: CRJBCDFBYWCYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(β-Benzoylvinyl)-m-chloranilin 在 对甲苯磺酰叠氮 、 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以61 mg的产率得到1-(3-chlorophenyl)-4-phenoyl-1,2,3-triazole
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975
• 作为产物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 、 3-氯苯胺 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N-(β-Benzoylvinyl)-m-chloranilin
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975

文献信息

• Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration
  作者：Yulei Zhao、Fangfang Zhang、Wenjun Yao、Chengyu Wang、Yuanyuan Liu、Yanzhong Li

  DOI：10.1002/ejoc.201501060

  日期：2015.12

  reaction[4] from aldehydes and phosphonate carbanions, enyne metathesis[5] from alkynes and alkenes, and cross-coupling reactions such as Negishi coupling,[6] Suzuki–Miyaura coupling,[7] and so on. The direct addition of the C–H bond of alkenes to alkynes catalyzed by transition metals has been explored by Trost,[8] Mitsudo/Kondo,[9] Murakami/Ito,[10] Yi,[11] Tsukuda,[12] Mori/Sato,[13] and Uemura.[14] Recently

  共轭二烯及其衍生物是无处不在的结构基序，存在于大量天然产物和药物中，例如胡萝卜素、维生素 A、lissoclinolide、bombykol、scyphotatin 和 viridenomycin。 [1] 由于两个共轭 π 键的独特反应性，二烯是多种重要工业和生物活性化合物的通用前体。 [2] 由于共轭二烯单元的重要性，寻找这些衍生物的有效合成引起了广泛关注。在过去的二十年里，过渡金属催化的交叉偶联经常被用于合成这种结构基序。 [3] 构建共轭二烯的经典方法包括来自醛和膦酸酯碳负离子的 Horner-Wadsworth-Emmons 反应 [4]，炔烃和烯烃的烯炔复分解[5]，以及交叉偶联反应，如根岸偶联，[6]铃木-宫浦偶联，[7]等。Trost，[8] Mitsudo/Kondo，[9] Murakami/Ito，[10] Yi，[11] Tsukuda，[12] 探索了在过渡金属催化下将烯烃的
• Multicomponent Cascade Reaction of 3-Formylchromones: Highly Selective Synthesis of Functionalized 9-Azabicyclo[3.3.1]nonane Derivatives
  作者：Ying-Gang Duan、Xing-Mei Hu、Xin-Ling Cao、Kai-Hong Lv、Sheng-Jiao Yan

  DOI：10.1021/acs.orglett.1c02431

  日期：2021.9.3

  A novel protocol for the preparation of functionalized 9-azabicyclo[3.3.1]nonane (ABCN) derivatives from 3-formylchromones, enaminones, and heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction has been developed by simply refluxing the mixture of the substrates 1–3. As a result, a series of ABCNs were produced through a very complex cascade reaction. This protocol can be used

  开发了一种通过前所未有的级联反应从 3-甲酰基色酮、烯胺酮和杂环烯酮缩醛胺 (HKAs) 制备功能化 9-氮杂双环 [3.3.1] 壬烷 (ABCN) 衍生物的新方案，方法是简单地回流基材1 – 3。结果，通过非常复杂的级联反应产生了一系列 ABCN。该协议可用于 ABCN 的合成，适用于一锅反应中 ABCN 天然类产品的组合和平行合成。
• Base-Promoted Synthesis of <i>N</i>-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer
  作者：Jie-Ping Wan、Shuo Cao、Yunyun Liu

  DOI：10.1021/acs.orglett.6b02975

  日期：2016.12.2

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.