(E)-4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide

• 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-(p-tolyl)ethylidene)benzenesulfonohydrazide
• 英文别名: 4-Methyl-N'-(1-p-tolylethylidene)benzenesulfonohydrazide；4-methyl-N-[(E)-1-(4-methylphenyl)ethylideneamino]benzenesulfonamide
• 化学式: C₁₆H₁₈N₂O₂S
• 分子量: 302.397
• InChiKey: PBRDDISAEJJRRH-SAPNQHFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-(dimethylamino)malononitrile 、 (E)-4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 在 zinc trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以73%的产率得到3-(p-tolyl)-1-tosyl-1H-pyrazole
  参考文献：
  名称：

  锌促进的甲苯磺酰hydr和2-（二甲基氨基）丙二腈的环化：合成取代的1-tosyl-1 H-吡唑的有效策略

  摘要：

  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。

  DOI：

  10.1039/c7cc04610c
• 作为产物：
  描述：

  对甲基苯乙酮 、 对甲苯磺酰肼 以 甲醇 为溶剂， 生成 (E)-4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide
  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

• Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides
  作者：Yu Zhao、Zitong Zhou、Man Chen、Weiguang Yang

  DOI：10.3390/molecules26123700

  日期：——

  amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR

  N-磺酰脒是由磺酰肼、末端炔烃和磺酰叠氮化物在室温下在甲苯中通过铜催化的三组分反应生成的。特别地，通过CuAAC/开环程序生成中间体N-磺酰烯酮亚胺，并与弱亲核磺酰肼进行亲核加成。此外，通过核磁共振氢谱仪测试了产品的稳定性。
• Palladium-Catalyzed One-Pot Synthesis of 5-(1-Arylvinyl)-1<i>H</i> -benzimidazoles: Overcoming the Limitation of Acetamide Partners
  作者：Timothée Naret、Pascal Retailleau、Jérôme Bignon、Jean-Daniel Brion、Mouad Alami、Abdallah Hamze

  DOI：10.1002/adsc.201600173

  日期：2016.6.2

  A new one‐pot palladium‐catalyzed process between N‐tosylhydrazones, N‐(dihalophenyl)‐imidates, and amines was designed. This reaction involves Barluenga cross‐coupling and N‐arylation followed by cyclization to produce functionalized benzimidazoles. During this transformation, one CC bond and two CN bonds were created by a single palladium‐catalyzed reaction. Depending on the starting materials

  设计了一种新的单锅钯催化方法，该方法在N-甲苯磺酰hydr，N-（二卤代苯基）-亚氨酸酯和胺之间进行。该反应涉及Barluenga交叉偶联和N芳基化，然后环化生成功能化的苯并咪唑。在这一转变过程中，通过一个钯催化的反应就产生了一个CC键和两个CN键。取决于起始材料，一个5-（1-芳基乙烯基）-1 H的库合成了苯并咪唑。在评估的几种芳基乙烯基苯并咪唑衍生物中，一种化合物在纳摩尔浓度范围内对人结肠癌细胞系（HCT-116）和人肺腺癌上皮细胞系（A549）表现出优异的抗增殖活性。
• <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。
• 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.