N'-(5-fluoro-2-(hex-1-yn-1-yl)benzylidene)-4-methylbenzenesulfonohydrazide | 1174271-12-5

• 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'-(5-fluoro-2-(hex-1-yn-1-yl)benzylidene)-4-methylbenzenesulfonohydrazide
• CAS: 1174271-12-5
• 化学式: C₂₀H₂₁FN₂O₂S
• 分子量: 372.463
• InChiKey: SFXDANMTKFIFRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N'-(5-fluoro-2-(hex-1-yn-1-yl)benzylidene)-4-methylbenzenesulfonohydrazide 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines via Multicomponent Reaction

  摘要：

  A highly efficient multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, alcohol, and alpha,beta-unsaturated aldehyde or ketone is disclosed, which generates the diverse H-pyrazolo[5,1-a]isoquinolines in good yields. This reaction proceeds with good functional group tolerance under mild conditions with high efficiency and excellent selectivity. Preliminary biological assays show that some of these compounds display promising activities as CDC25B inhibitor, TC-PTP inhibitor, and PTP1B inhibitor.

  DOI：

  10.1021/ol101988q
• 作为产物：
  描述：

  5-fluoro-2-(hex-1-yn-1-yl)benzaldehyde 、 对甲苯磺酰肼 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 N'-(5-fluoro-2-(hex-1-yn-1-yl)benzylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  Efficient Generation of Biologically Active H-Pyrazolo[5,1-a]isoquinolines via Multicomponent Reaction

  摘要：

  A highly efficient multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, alcohol, and alpha,beta-unsaturated aldehyde or ketone is disclosed, which generates the diverse H-pyrazolo[5,1-a]isoquinolines in good yields. This reaction proceeds with good functional group tolerance under mild conditions with high efficiency and excellent selectivity. Preliminary biological assays show that some of these compounds display promising activities as CDC25B inhibitor, TC-PTP inhibitor, and PTP1B inhibitor.

  DOI：

  10.1021/ol101988q

文献信息

• AgOTf-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alkyne
  作者：Zhiyuan Chen、Xiaodi Yang、Jie Wu

  DOI：10.1039/b904498a

  日期：——

  AgOTf-catalyzed tandem reactions of N'-(2-alkynylbenzylidene)hydrazides with various alkynes under mild conditions are described, which generate fused 1,2-dihydroisoquinolines in good to excellent yields.

  描述了在温和的条件下，N'-（2-炔基亚苄基）酰肼与各种炔烃的AgOTf催化串联反应，该反应以良好或极好的收率产生了稠合的1,2-二氢异喹啉。
• Generation of Polyfluoroaryl‐Fused <i>H</i> ‐Pyrazolo[5,1‐ <i>a</i> ]isoquinolines through a Reaction of <i>N</i> ′‐(2‐Alkynylbenzylidene)hydrazide with Polyfluoroarene
  作者：Ling Zhang、Qian Xiao、Shengqing Ye、Jie Wu

  DOI：10.1002/asia.201200227

  日期：2012.8

  Polyfluoroarene reacts with N′‐(2‐alkynylbenzylidene)hydrazide catalyzed by silver triflate in the presence of cesium carbonate, leading to polyfluoroaryl‐fused H‐pyrazolo[5,1‐a]isoquinolines in good yields.

  与Polyfluoroarene发生反应Ñ ' - （2- alkynylbenzylidene）酰肼通过三氟甲磺酸银在碳酸铯的存在下催化的，导致polyfluoroaryl稠合ħ -吡唑并[5,1-一个以良好产率]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。
• Multicatalytic tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with indole
  作者：Xingxin Yu、Xiaodi Yang、Jie Wu

  DOI：10.1039/b913409c

  日期：——

  The combination of AgOTf and Dy(OTf)3 shows high efficiency as a catalyst in the tandem reactions of N′-(2-alkynylbenzylidene)hydrazides with indoles, which generate the unexpected 1-(indol-3-yl)-2-aminoisoquinolinium triflates in good yields.

  AgOTf和Dy（OTf）3的组合在N '-（2-炔基亚苄基）酰肼与吲哚的串联反应中显示出高效率，可生成意外的1-（吲哚-3-基）-2-氨基异喹啉三叶草产量高。
• Synthesis of pyrazolo[5,1-a]isoquinolines via silver(i)–rhodium(i) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with cycloprop-2-ene-1,1-dicarboxylate
  作者：Liangqing Yao、Xingxin Yu、Chen Mo、Jie Wu

  DOI：10.1039/c2ob26824h

  日期：——

  A tandem reaction between N′-(2-alkynylbenzylidene)hydrazide and cycloprop-2-ene-1,1-dicarboxylate co-catalyzed by silver triflate and tris(triphenylphosphine)rhodium chloride is reported. The reaction proceeds through 6-endo-cyclization, [3 + 2] cycloaddition, cyclopropane opening, and aromatization, leading to pyrazolo[5,1-a]isoquinolines in moderate to good yields.

  N '-（2-炔基亚苄基）酰肼与环丙-2-烯-1,1-二羧酸酯共催化下的串联反应三氟甲磺酸银报道了三（三苯基膦）氯化铑。该反应通过6-内-cyclization，[3 + 2]环加成，环丙烷打开并进行芳构化，导致吡唑并[5,1- a ]异喹啉的产量适中至良好。