N'-(2-((4-methoxyphenyl)ethynyl)benzylidene)benzenesulfonohydrazide | 1176334-74-9

• 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'-(2-((4-methoxyphenyl)ethynyl)benzylidene)benzenesulfonohydrazide
• CAS: 1176334-74-9
• 化学式: C₂₂H₁₈N₂O₃S
• 分子量: 390.463
• InChiKey: BCCBMFRMEVGQMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-(2-((4-methoxyphenyl)ethynyl)benzylidene)benzenesulfonohydrazide 、 亚磷酸二乙酯 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 以67%的产率得到diethyl (3-(4-methoxyphenyl)isoquinolin-1-yl)phosphonate
  参考文献：
  名称：

  Lewis acid-catalyzed reactions of N′-(2-alkynylbenzylidene)hydrazides with diethyl phosphite

  摘要：

  Lewis acid catalyst-tuned reactions of N'-(2-alkynylbenzylidene)hydrazides with diethyl phosphite are described. Isoquinolin-1-ylphosphonate is generated when copper triflate is utilized as catalyst, while 2-amino-1,2-dihydroisoquinolin-1-ylphosphonate is obtained in the presence of palladium acetate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.013

文献信息

• Silver Triflate-Catalyzed or Electrophile-Mediated Tandem Reaction of<i>N′</i>-(2-Alkynylbenzylidene)hydrazides with Dimethyl Acetylenedicarboxylate
  作者：Zhiyuan Chen、Qiuping Ding、Xingxin Yu、Jie Wu

  DOI：10.1002/adsc.200900131

  日期：2009.7

  Different outcomes were generated under different conditions for the tandem reactions of N′‐(2‐alkynylbenzylidene)hydrazides with dimethyl acetylenedicarboxylate (DMAD) catalyzed by silver triflate or in the presence of electrophiles. The unexpected isoquinoline‐based azomethine ylides were obtained when the reaction was catalyzed by silver triflate or in the presence of bromine, while the fused 1

  三氟甲磺酸银或在亲电子试剂的存在下，N' -（2-炔基亚苄基）酰肼与乙炔二羧酸二甲酯（DMAD）的串联反应在不同条件下产生了不同的结果。当在三氟甲磺酸银或溴的存在下催化反应时，获得了出乎意料的基于异喹啉的偶氮甲亚胺，而在上述串联反应中使用碘时，得到了稠合的1,2-二氢异喹啉。
• Tandem Reactions of <i>N</i>′-(2-Alkynylbenzylidene)hydrazides with Silyl Enolates: A Facile Route to <i>H</i>-Pyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Xingxin Yu、Zhiyuan Chen、Xiaodi Yang、Jie Wu

  DOI：10.1021/cc1000314

  日期：2010.5.10

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with silyl enolate is described, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good to excellent yields. Intramolecular cyclization, nucleophilic addition, condensation, and aromatization may be involved in the reaction process.

  描述了N '-（2-炔基亚苄基）酰肼与烯丙基甲硅烷基酯的三氟甲磺酸银催化串联反应，可产生出人意料的H-吡唑并[5,1- a ]异喹啉，收率高至优异。反应过程中可能涉及分子内环化，亲核加成，缩合和芳构化。
• Synthesis of 2-(Trifluoromethyl)-[1,2,4]triazolo[5,1-a]isoquinoline via Cycloaddition ofC,N-Cyclic Azomethine Imine with CF3CN
  作者：Zhezuo Chen、Shouxiong Chen、Zhanyan Qiu、Bo Lin、Yunfei Yao、Fafu Yang、Zhiqiang Weng

  DOI：10.1021/acs.joc.4c00557

  日期：2024.5.17

  A [3 + 2] cycloaddition of C,N-cyclic azomethine imine with in situ-generated CF3CN for the construction of 2-(trifluoromethyl)-[1,2,4]triazolo[5,1-a]isoquinoline is reported. Remarkably, this process shows a broad substrate scope with excellent functional group tolerance, which is scalable and enables a practical route to a library of 2-(trifluoromethyl)-[1,2,4]triazolo[5,1-a]isoquinoline derivatives

  C , N-环状偶氮甲碱亚胺与原位生成的 CF 3 CN 进行 [3 + 2] 环加成，用于构建 2-(三氟甲基)-[1,2,4]三唑并[5,1- a ]异喹啉：报道称。值得注意的是，该过程显示出广泛的底物范围和出色的官能团耐受性，可扩展并为构建 2-(三氟甲基)-[1,2,4]三唑并[5,1- a ]异喹啉衍生物库提供了一条实用途径中等至良好的产量。