N'-(1-(2,4-dichlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide | 1269207-66-0

• 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: N'-(1-(2,4-dichlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
• 英文别名: N-[1-(2,4-dichlorophenyl)ethylideneamino]-4-methylbenzenesulfonamide
• CAS: 1269207-66-0
• 化学式: C₁₅H₁₄Cl₂N₂O₂S
• 分子量: 357.26
• InChiKey: GWBJIJVSPICPQF-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C
• 沸点：
  484.7±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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'-(1-(2,4-dichlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 在 potassium carbonate 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以81%的产率得到N-(1-(2,4-dichlorophenyl)ethyl)-N'-(1-(2,4-dichlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  Base and solvent mediated decomposition of tosylhydrazones: highly selective synthesis of N-alkyl substituted hydrazones, dialkylidenehydrazines, and oximes

  摘要：

  Base and solvent mediated decomposition of tosylhydrazones was studied. It was found that reaction of tosylhydrazones in CH3NO2 in the presence of 1 equiv of K2CO3 in 90 degrees C gave N-alkylated products in 52-96% yield. However, when the same reaction was carried out in mixed solvent of CH3NO2 and dioxane in the presence of 3 equiv of NaOH at 110 degrees C, dialkylidenehydrazines were obtained in moderate to high yield. If the reaction was carried out in mixed solvent of CH3NO2 and DMSO in the presence of 10 equiv of NaOH at 110 degrees C, CH3NO2 can act as the precursor of hydroxylamine and corresponding oximes were formed in up to 92% yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.055
• 作为产物：
  描述：

  对甲苯磺酰肼 、 2,4-二氯苯乙酮 以 甲醇 为溶剂， 生成 N'-(1-(2,4-dichlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  铜催化的 1,3-唑与 N-甲苯磺酰腙的直接苄基化或烯丙基化

  摘要：

  铜催化的 N-甲苯磺酰腙与 1,3-唑的交叉偶联导致直接的 CH 苄基化或烯丙基化。提出Cu卡宾迁移插入在这种转变中起关键作用。

  DOI：

  10.1021/ja111249p

文献信息

• Directed C–C bond cleavage of a cyclopropane intermediate generated from<i>N</i>-tosylhydrazones and stable enaminones: expedient synthesis of functionalized 1,4-ketoaldehydes
  作者：Meiyan Ni、Jianguo Zhang、Xiaoyu Liang、Yaojia Jiang、Teck-Peng Loh

  DOI：10.1039/c7cc07178g

  日期：——

  -quaternary centers via regioseletive C-C bond activation has been described. Through cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring affords the 1, 4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioseletivity.

  已经描述了一种有效的方法，该方法通过区域选择性CC键活化来构建带有全碳原子的α-季中心的官能化的1，4-酮醛。通过使用原位生成的N-甲苯磺酰hydr酮重氮试剂对稳定的烯胺酮进行环丙烷化，然后选择性地将CC裂解成环丙烷环，可得到1,4-酮醛衍生物，收率好至极佳。该方法适用于较宽的底物范围和较高的重复性。
• Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct CH Bond Functionalization
  作者：Shuai Xu、Guojiao Wu、Fei Ye、Xi Wang、Huan Li、Xia Zhao、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201412450

  日期：2015.4.7

  The copper(I)‐catalyzed alkylation of electron‐deficient polyfluoroarenes with N‐tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp2)C(sp3) bonds with polyfluoroarenes through direct CH bond functionalization. Mechanistically, copper(I) carbene

  已经开发了N-甲苯磺酰hydr和重氮化合物对缺电子的多氟芳烃进行铜（I）催化的烷基化反应。该反应使用容易获得的起始原料并且操作简单，因此代表了通过直接的CH键官能化与多氟芳烃构建C（sp 2）C（sp 3）键的实用方法。从机理上讲，铜（I）卡宾的形成和随后的迁移插入被认为是反应途径中的关键步骤。
• Palladium(<scp>ii</scp>)-catalyzed direct O-alkenylation of 2-arylquinazolinones with N-tosylhydrazones: an efficient route to O-alkenylquinazolines
  作者：Rajaka Lingayya、Mari Vellakkaran、Kommu Nagaiah、Prabhakar Rao Tadikamalla、Jagadeesh Babu Nanubolu

  DOI：10.1039/c6cc09445g

  日期：——

  An efficient Pd(ii)-catalyzed direct O-alkenylation of 2-arylquinazolinones with simple ketone-derived N-tosylhydrazones is reported.

  报道了一种高效的Pd（II）催化的直接2-芳基喹唑酮与简单酮衍生的N-对甲苯磺酰肼烯烃化反应。
• Palladium-Catalyzed Oxidative Cross-Coupling of <i>N-</i>Tosylhydrazones with Indoles: Synthesis of <i>N-</i>Vinylindoles
  作者：Xiaobao Zeng、Guolin Cheng、Jinhai Shen、Xiuling Cui

  DOI：10.1021/ol401217h

  日期：2013.6.21

  A general and efficient palladium-catalyzed oxidative cross-coupling reaction of N-tosylhydrazones with indoles providing N-vinylindoles has been developed. The reaction proceeds smoothly with various indoles and N-tosylhydrazones in a stereocontrolled manner, and a wide variety of N-vinylindoles were obtained up to 99% yields for 26 examples.