N-acetyl-4-methylbenzenesulfonohydrazide | 1192307-50-8

• 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-acetyl-4-methylbenzenesulfonohydrazide
• 英文别名: N-acetyl-N-tosylhydrazine；N,N-acetyltosylhydrazine；N,N-acyltosylhydrazine；N-(4-methylphenyl)sulfonylacetohydrazide
• CAS: 1192307-50-8
• 化学式: C₉H₁₂N₂O₃S
• 分子量: 228.272
• InChiKey: TVLICSCTJSHPQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  382.5±35.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-4-methylbenzenesulfonohydrazide 在 sodium methylate 、 mercuric triflate 、 碳酸氢钠 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 12.0h， 生成 N'-(cyclohex-2-en-1-yl)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  三氟甲磺酸汞催化剂促进烯丙基甲硅烷基醚与酰肼形成碳-氮键

  摘要：

  使用 2 mol% 的三氟甲磺酸汞 [Hg(OTf) 2 ] 作为催化剂，在非常温和的条件下开发了一种在烯丙基甲硅烷基醚和 N , N - 酰基甲苯基肼之间形成碳 - 氮键的有效方法。该方法不需要使用任何配体系统或辅助添加剂，适用于制备各种N-烯丙基酰肼，收率良好。

  DOI：

  10.1055/s-0031-1290758
• 作为产物：
  描述：

  乙酸酐 、 对甲苯磺酰肼 在 4-氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到N-acetyl-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide

  摘要：

  An efficient and simple method for selective acylation of either one of two nitrogen atoms of tosylhydrazide was developed. The selectivity was drastically controlled by a catalytic amount of 4-aminopyridine or 4-(dimethylamino)pyridine with common acylating agents. The nitrogen atom masked with a tosyl group was acylated in the presence of 4-aminopyridine, whereas the primary nitrogen atom was acylated in the absence of 4-aminopyridine.

  DOI：

  10.1021/ol9021194

文献信息

• Facile One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles from Propargylic Alcohols via Propargyl Hydrazides
  作者：Chada Raji Reddy、Jonnalagadda Vijaykumar、René Grée

  DOI：10.1055/s-0032-1316856

  日期：——

  A new and efficient metal-free, two-component, one-pot approach to a variety of 3,5-disubstituted 1H-pyrazoles has been developed from propargylic alcohols. This transformation proceeds via an acid-catalyzed propargylation of N,N-diprotected hydrazines followed by base-mediated 5-endo-dig cyclization leading to 3,5-disubstituted 1H-pyrazoles in good overall yields.
• 4-Aminopyridine Catalyzed Direct and Regioselective Acylation of <i>N</i>-Tosylhydrazide
  作者：Kosuke Namba、Isamu Shoji、Mugio Nishizawa、Keiji Tanino

  DOI：10.1021/ol9021194

  日期：2009.11.5

  An efficient and simple method for selective acylation of either one of two nitrogen atoms of tosylhydrazide was developed. The selectivity was drastically controlled by a catalytic amount of 4-aminopyridine or 4-(dimethylamino)pyridine with common acylating agents. The nitrogen atom masked with a tosyl group was acylated in the presence of 4-aminopyridine, whereas the primary nitrogen atom was acylated in the absence of 4-aminopyridine.
• Carbon-Nitrogen Bond Formation between Allyl Silyl Ether and Hydrazide Promoted by Mercuric Triflate Catalyst
  作者：Hirofumi Yamamoto、Naoto Yamasaki、Shingo Yoshidome、Ikuo Sasaki、Kosuke Namba、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1055/s-0031-1290758

  日期：2012.4

  An efficient method for carbon–nitrogen bond formation between ally silyl ethers and N , N -acyltosylhydrazine was developed under very mild conditions using 2 mol% of mercuric triflate [Hg(OTf) 2 ] as a catalyst. This method does not require the use of any ligand system or supplementary additives and is applicable to the preparation of various N -allylhydrazides with good to excellent yields.

  使用 2 mol% 的三氟甲磺酸汞 [Hg(OTf) 2 ] 作为催化剂，在非常温和的条件下开发了一种在烯丙基甲硅烷基醚和 N , N - 酰基甲苯基肼之间形成碳 - 氮键的有效方法。该方法不需要使用任何配体系统或辅助添加剂，适用于制备各种N-烯丙基酰肼，收率良好。