N'-(4-methoxy-2-(phenylethynyl)benzylidene)-4-methylbenzenesulfonohydrazide | 1239452-58-4

• 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'-(4-methoxy-2-(phenylethynyl)benzylidene)-4-methylbenzenesulfonohydrazide
• CAS: 1239452-58-4
• 化学式: C₂₃H₂₀N₂O₃S
• 分子量: 404.489
• InChiKey: GYOOMOQOQPNLRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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'-(4-methoxy-2-(phenylethynyl)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：

  4-methoxy-2-(phenylethynyl)benzaldehyde 、 对甲苯磺酰肼 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 N'-(4-methoxy-2-(phenylethynyl)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

• 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。
• An unexpected three-component reaction of 2-alkylenecyclobutanone and N′-(2-alkynylbenzylidene)hydrazide with water
  作者：Xiaolin Pan、He Wang、Hong-Guang Xia、Jie Wu

  DOI：10.1039/c5ra17787a

  日期：——

  A silver(i)-catalyzed three-component reaction of 2-alkylenecyclobutanone, N′-(2-alkynylbenzylidene)hydrazide with water gives rise to 3-(pyrazolo[5,1-a]isoquinolin-1-yl)propanoic acids in good yields through 6-endo cyclization, [3 + 2] cycloaddition, and rearrangement.

  一种银（i）催化的2-烯基环丁酮，N'-(2-炔基苄亚甲基)腙与水的三组分反应，通过6-内环化，[3 + 2]环加成和重排反应，产生了3-(吡唑并[5,1-a]异喹啉-1-基)丙酸，收率较高。
• 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。
• Synthesis of H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol
  作者：Wenyan Hao、Tinli Zhang、Mingzhong Cai

  DOI：10.1016/j.tet.2013.08.049

  日期：2013.11

  A silver triflate-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alcohol is reported, which generates H-pyrazolo[5,1-a]isoquinoline derivatives in good yields under mild conditions.

  的三氟甲磺酸银催化的串联反应Ñ ' - （2- alkynylbenzylidene）与醇酰肼报道，其产生ħ -吡唑并[5,1-一个在温和的条件下良好的产率]异喹啉衍生物。
• Silver triflate and N-heterocyclic carbene co-catalyzed reaction of N′-(2-alkynylbenzylidene)hydrazide, methanol with α,β-unsaturated aldehyde
  作者：Zhiyuan Chen、Xingxin Yu、Jie Wu

  DOI：10.1039/c0cc01207f

  日期：——

  A highly efficient silver triflate and N-heterocyclic carbene co-catalyzed three-component reaction of N′-(2-alkynylbenzylidene)hydrazide, methanol with α,β-unsaturated aldehyde is described, which gives rise to the 2-amino-1,2-dihydroisoquinolines in good yield.

  高效协同催化的银三氟磺酸盐与N-杂环卡宾三组分反应：N²-(2-炔基亚苄基)酰肼、甲醇与α,β-不饱和醛反应生成2-氨基-1,2-二氢异喹啉，收率良好。