4-methyl-N'-((3-(phenylethynyl)thiophen-2-yl)methylene)benzenesulfonohydrazide | 1319204-76-6

• 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: 4-methyl-N'-((3-(phenylethynyl)thiophen-2-yl)methylene)benzenesulfonohydrazide
• CAS: 1319204-76-6
• 化学式: C₂₀H₁₆N₂O₂S₂
• 分子量: 380.491
• InChiKey: UMVDXAMGPKCUQR-UHFFFAOYSA-N

物化性质

• 沸点：
  574.4±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-methyl-N'-((3-(phenylethynyl)thiophen-2-yl)methylene)benzenesulfonohydrazide 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 (5-phenylthieno[2,3-c]pyridin-6-ium-6-yl)(tosyl)amide
  参考文献：
  名称：

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed reaction of N′-(2-alkynylbenzylidene)hydrazide with allenoate

  摘要：

  A silver triflate-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with allenoate under mild conditions is described, which provides an efficient approach to diverse H-pyrazolo[5,1-alisoquinolines. This reaction proceeds with a wide substrate scope with good functional groups tolerance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.013

文献信息

• Three-Component Reaction of <i>N</i>′-(2-Alkynylbenzylidene)hydrazide, Alkyne, with Sulfonyl Azide via a Multicatalytic Process: A Novel and Concise Approach to 2-Amino-<i>H</i>-pyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Shaoyu Li、Yong Luo、Jie Wu

  DOI：10.1021/ol201653j

  日期：2011.8.19

  A novel and efficient route for the synthesis of 2-amino-H-pyrazolo[5,1-a]isoquinolines via a three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, alkyne, and sulfonyl azide is described. This transformation, co-catalyzed by silver triflate and copper(I) bromide under mild conditions, proceeds efficiently to generate the 2-amino-H-pyrazolo[5,1-a]isoquinolines in good to excellent yields

  一种用于2-氨基的合成新颖的和有效的路由ħ -吡唑并[5,1-一个]异喹啉通过三组分的反应Ñ ' - （2- alkynylbenzylidene基）酰肼，炔，和磺酰基叠氮进行说明。这种转变，共催化的温和条件下，通过三氟甲磺酸银和铜（I）溴化物，可有效地进行生成2-氨基- ħ -吡唑并[5,1-一个]异喹啉在良好至优异的产量。
• Transition‐Metal Free Construction of Isoquinoline‐fused Triazines Containing Alkenyl C−X Bonds
  作者：Xiao Cheng、Xia Cao、Shuang‐Jing Zhou、Bao‐Gui Cai、Xiang‐Kui He、Jun Xuan

  DOI：10.1002/adsc.201801181

  日期：2019.3.15

  in situ formed C,N‐cyclic azomethine imines is reported. This one‐pot transition metal‐free cycloaddition process exhibits broad substrate scope, excellent functional group tolerance, and affords a series of biologically important isoquinoline‐fused triazines in good to excellent yields, which containing valuable alkenyl C−X bonds (X=Br, I).

  卤素和碱介导的[3 + 3] -环的反应原位生成azaoxyallyl阳离子与原位报道形成C，N环状甲亚胺亚胺。这种单锅无过渡金属的环加成过程具有广泛的底物范围，出色的官能团耐受性，并提供了一系列生物学上重要的异喹啉融合的三嗪，其收率高至优异，其中包含有价值的烯基C-X键（X = Br，一世）。
• Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Silver(I)-Catalyzed Tandem Reaction of N′-(2-Alkynylbenzylidene)hydrazides with Propargyl Amine Derivatives
  作者：Zhiyong Wang、Gang Liu、Hongliang Liu、Shouzhi Pu

  DOI：10.1055/s-0033-1340486

  日期：——

  Abstract We have developed a tandem reaction of N′-(2-alkynylbenzylidene)hydrazides with propargyl amine derivatives catalyzed by silver triflate to provide 2-(aminomethyl)-H-pyrazolo[5,1-a]isoquinolines. This reaction proceeds through a tandem 6-endo-cyclization, nucleophilic addition, 5-endo-cyclization and aromatization, leading to the cycloadducts in moderate to good yields with exclusive regioselectivity

  摘要 我们已经开发的一个串联反应Ñ ' - （2- alkynylbenzylidene）与三氟甲磺酸银催化以提供炔丙基胺衍生物酰肼2-（氨基甲基） - H ^ -吡唑并[5,1-一个]异喹啉。这通过一个串联反应进行6-内切-cyclization，亲核加成，5-内切-cyclization和芳构化，导致在cycloadducts中度至良好的产率与独占的区域选择性。 我们已经开发的一个串联反应Ñ ' - （2- alkynylbenzylidene）与三氟甲磺酸银催化以提供炔丙基胺衍生物酰肼2-（氨基甲基） - H ^ -吡唑并[5,1-一个]异喹啉。这通过一个串联反应进行6-内切-cyclization，亲核加成，5-内切-cyclization和芳构化，导致在cycloadducts中度至良好的产率与独占的区域选择性。
• Silver triflate–copper(ii) acetate cooperative catalysis in a cascade reaction for concise synthesis of 2-carbonyl H-pyrazolo[5,1-a]isoquinolines
  作者：Zhiyuan Chen、Liang Gao、Shengqing Ye、Qiuping Ding、Jie Wu

  DOI：10.1039/c2cc30413a

  日期：——

  A cascade reaction of N'-(2-alkynylbenzylidene)hydrazide with allenoate in the presence of dioxygen co-catalyzed by silver triflate and copper(II) acetate under mild conditions is described, which provides an efficient approach to 2-carbonyl H-pyrazolo[5,1-a]isoquinolines.

  描述了N'-（2-炔基亚苄基）酰肼与脲酸酯在温和条件下由三氟甲磺酸银和乙酸铜（II）共同催化的双氧的级联反应，这为2-羰基H-吡唑啉酮提供了一种有效的方法[5，1-a]异喹啉。
• A silver(I)–rhodium(I) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with 2-vinyloxirane
  作者：Hongliang Liu、Gang Liu、Guanyinsheng Qiu、Shouzhi Pu、Jie Wu

  DOI：10.1016/j.tet.2012.12.018

  日期：2013.2

  A novel and efficient route to H-pyrazolo[5,1-a]isoquinoline-1-carbaldehydes via a tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with 2-vinyloxirane is described. The reaction proceeds through a silver(I)–rhodium(I) cooperative catalysis.

  描述了通过N '-（2-炔基亚苄基）酰肼与2-乙烯基环氧乙烷的串联反应制备H-吡唑并[5,1- a ]异喹啉-1-甲醛的新颖有效途径。该反应通过银（I）-铑（I）协同催化进行。