(E)-N'-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide | 1421692-99-0

• 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)-N'-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
• 英文别名: N-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide；N-[(E)-1-(4-chlorophenyl)ethylideneamino]-4-methylbenzenesulfonamide
• CAS: 1421692-99-0
• 化学式: C₁₅H₁₅ClN₂O₂S
• 分子量: 322.815
• InChiKey: LXTKFUSDWSCUJN-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N'-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以50%的产率得到(E)-N-(1-(4-chlorophenyl)ethyl)-N'-(1-(4-chlorophenyl)ethylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  N-Alkylation of tosylhydrazones via a metal-free reductive coupling procedure

  摘要：

  A simple metal-free route for the N-alkylation of tosylhydrazones is described via the NaOMe-promoted reductive coupling of tosylhydrazones under mild conditions. A wide variety of N-alkylated tosylhydrazones were obtained in moderate to good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.124
• 作为产物：
  描述：

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

  N-甲苯磺酰hydr与芳基硼酸的Pd催化氧化交叉偶联。

  摘要：

  N-甲苯磺酰hydr和芳基硼酸的Pd催化反应提供了烯烃衍生物。建议该氧化交叉偶联通过Pd卡宾中间体的迁移插入过程进行。

  DOI：

  10.1039/b925590g

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。
• Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles
  作者：Bang-Hong Zhang、Lin-Sheng Lei、Si-Zhan Liu、Xue-Qing Mou、Wei-Ting Liu、Shao-Hua Wang、Jie Wang、Wen Bao、Kun Zhang

  DOI：10.1039/c7cc04610c

  日期：——

  A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.

  已成功开发了甲苯磺酰肼与2-（二甲氨基）丙二腈的Zn（OTf）2促进的环化反应，为合成取代的1-tosyl-1 H-吡唑提供了有效的策略。
• Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids
  作者：Xia Zhao、Jing Jing、Kui Lu、Yan Zhang、Jianbo Wang

  DOI：10.1039/b925590g

  日期：——

  The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.

  N-甲苯磺酰hydr和芳基硼酸的Pd催化反应提供了烯烃衍生物。建议该氧化交叉偶联通过Pd卡宾中间体的迁移插入过程进行。
• <b>Hydrohydrazination of Arylalkynes Catalyzed by an Expanded Ring N-Heterocyclic Carbene (er-NHC) Gold Complex Under Solvent-Free Conditions</b>
  作者：Oleg S. Morozov、Pavel S. Gribanov、Andrey F. Asachenko、Pavel V. Dorovatovskii、Victor N. Khrustalev、Viktor B. Rybakov、Mikhail S. Nechaev

  DOI：10.1002/adsc.201500658

  日期：2016.4.28

  electron donating, sterically bulky THD‐Dipp (1,3‐bis(2,6‐diisopropylphenyl)hexahydro‐2H‐1,3‐diazepine‐2‐ylidene) seven‐membered N‐heterocyclic carbene ligand, efficiently promotes intermolecular addition of Ts‐ and Boc‐hydrazine to arylalkynes under solvent‐free conditions.

  [（THD-Dipp）AuOTf]，受强电子给体，空间庞大的THD-Dipp（1,3-二（2,6-二异丙基苯基）六氢-2 H -1,3-二氮杂-2-亚基）的支持7 N元杂环卡宾配体可在无溶剂条件下有效促进Ts和Boc肼分子间加成至芳炔基。
• 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.