(E)-4-methyl-N′-(1-(thiophen-2-yl)ethylidene)benzene-1-sulfonohydrazide | 68728-03-0

• 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: (E)-4-methyl-N′-(1-(thiophen-2-yl)ethylidene)benzene-1-sulfonohydrazide
• 英文别名: (E)-4-methyl-N'-(1-(thiophen-2-yl)ethylidene)benzenesulfonohydrazide；4-Methyl-N'-(1-(2-thienyl)ethylidene)benzenesulfonohydrazide；4-methyl-N-[(E)-1-thiophen-2-ylethylideneamino]benzenesulfonamide
• CAS: 68728-03-0
• 化学式: C₁₃H₁₄N₂O₂S₂
• 分子量: 294.398
• InChiKey: QYIGWVSKOVPXJX-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-氨基-3-苯基-2-丙烯酸乙酯 、 (E)-4-methyl-N′-(1-(thiophen-2-yl)ethylidene)benzene-1-sulfonohydrazide 在 叔丁基过氧化氢 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以54%的产率得到ethyl 2-phenyl-5-(thiophene-2-yl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Visible-Light-Induced C (sp³)–H Functionalization of Tosylhydrazones: Synthesis of Polysubstituted Pyrroles under Metal-Free Conditions

  摘要：

  Iodine catalyzed C (sp(3))-H functionalization of tosylhydrazones with beta-enamino esters under visible light irradiation for the synthesis of trisubstituted pyrroles has been described. The present method is also applicable to a alpha-substituted tosylhydrazones to yield the tetra-substituted pyrroles.

  DOI：

  10.1021/acs.joc.8b00878
• 作为产物：
  描述：

  2-乙酰基噻吩 、 对甲苯磺酰肼 以 正己烷 为溶剂， 以81%的产率得到(E)-4-methyl-N′-(1-(thiophen-2-yl)ethylidene)benzene-1-sulfonohydrazide
  参考文献：
  名称：

  I₂–TBHP-Catalyzed Oxidative Cross-Coupling of N-Sulfonyl Hydrazones and Isocyanides to 5-Aminopyrazoles

  摘要：

  I-2-TBHP-catalyzed oxidative cross coupling of N-sulfonyl hydrazones with isocyanides has been realized for the synthesis of 5-aminopyrazoles through formal [4 + 1] annulation via in situ azoalkene formation. Notable features are the metal/alkyne-free strategy, C-C and C-N bond formation, atom economy, catalytic I-2, broad functional group tolerance, good reaction yields, shorter time, and also applicability to one-pot methodology.

  DOI：

  10.1021/acs.orglett.5b00398

文献信息

• 一类噻吩-3(2H)-酮类化合物及其合成方法
  申请人：华东师范大学

  公开号：CN112778267A

  公开（公告）日：2021-05-11

  本发明公开了一种噻吩‑3(2H)‑酮类化合物及其合成方法，其合成方法是以式(1)所示的N‑烷基‑N‑芳基硫代酰胺和式(2)所示的N‑对甲苯磺酰腙作为原料，在钯催化剂、膦配体、无机碱和Lewis酸的存在下，在有机溶剂中，温度为70～130℃的条件下，发生由卡宾参与的金属催化串联反应得到所述式(3)的噻吩‑3(2H)‑酮类化合物。本发明噻吩‑3(2H)‑酮类化合物的合成方法通过条件控制，具有操作简单、原子经济、步骤经济、绿色高效、底物适用范围广等优点。
• I₂–TBHP-Catalyzed Oxidative Cross-Coupling of <i>N</i>-Sulfonyl Hydrazones and Isocyanides to 5-Aminopyrazoles
  作者：Gopal Chandru Senadi、Wan-Ping Hu、Ting-Yi Lu、Amol Milind Garkhedkar、Jaya Kishore Vandavasi、Jeh-Jeng Wang

  DOI：10.1021/acs.orglett.5b00398

  日期：2015.3.20

  I-2-TBHP-catalyzed oxidative cross coupling of N-sulfonyl hydrazones with isocyanides has been realized for the synthesis of 5-aminopyrazoles through formal [4 + 1] annulation via in situ azoalkene formation. Notable features are the metal/alkyne-free strategy, C-C and C-N bond formation, atom economy, catalytic I-2, broad functional group tolerance, good reaction yields, shorter time, and also applicability to one-pot methodology.
• Visible-Light-Induced C (sp³)–H Functionalization of Tosylhydrazones: Synthesis of Polysubstituted Pyrroles under Metal-Free Conditions
  作者：N. Naresh Kumar Reddy、Deepa Rawat、Subbarayappa Adimurthy

  DOI：10.1021/acs.joc.8b00878

  日期：2018.8.17

  Iodine catalyzed C (sp(3))-H functionalization of tosylhydrazones with beta-enamino esters under visible light irradiation for the synthesis of trisubstituted pyrroles has been described. The present method is also applicable to a alpha-substituted tosylhydrazones to yield the tetra-substituted pyrroles.