N‘-methyl-N‘-phenylbenzenesulfonohydrazide

• 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‘-methyl-N‘-phenylbenzenesulfonohydrazide
• 英文别名: N′-methyl-N′-phenylbenzenesulfonohydrazide；N'-methyl-N'-phenylbenzenesulfonohydrazide；benzenesulfonic acid-(N'-methyl-N'-phenyl-hydrazide)；Benzolsulfonsaeure-(N'-methyl-N'-phenyl-hydrazid)；Benzolsulfonsaeure-(β-methyl-β-phenyl-hydrazid)；β-Benzolsulfonyl-α-methyl-phenylhydrazin
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: MVFSSJKMQUDTLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N‘-methyl-N‘-phenylbenzenesulfonohydrazide 、 1,2-二溴乙烷 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以75%的产率得到(E)-1-methyl-1-phenyl-2-(2-(phenylsulfonyl)ethylidene)hydrazine
  参考文献：
  名称：

  四氟硼酸芳基重氮，二氧化硫，1,2-二溴乙烷和肼的四组分反应† ‡

  摘要：

  描述了四氟硼酸芳基重氮鎓，二氧化硫，1,2-二溴乙烷和肼在无金属条件下的四组分反应，为2-芳基磺酰基yl提供了一种新颖而有效的方法。通过在温和的条件下以良好的官能团耐受性插入二氧化硫，可顺利进行转化。

  DOI：

  10.1039/c5ob01765c
• 作为产物：
  描述：

  1-甲基-1-苯肼 、 苯磺酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 以70%的产率得到N‘-methyl-N‘-phenylbenzenesulfonohydrazide
  参考文献：
  名称：

  N-Aminoindoline derivatives as inhibitors of 5-lipoxygenase

  摘要：

  N-Aminoindoline derivatives were prepared and their 5-lipoxygenase inhibitory activities were evaluated in vitro and compared with those of phenidone and NDGA. Compound 4 presents the most effective 5-LO inhibition. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00077-4

文献信息

• A Copper-Catalyzed Three-Component Reaction of Triethoxysilanes, Sulfur Dioxide, and Hydrazines
  作者：Xianbo Wang、Lijun Xue、Zhiyong Wang

  DOI：10.1021/ol5018849

  日期：2014.8.1

  A three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate is reported, leading to N-aminosulfonamides in good yields. Not only triethoxy(aryl)silanes but also triethoxy(alkyl)silanes are compatible during the process of insertion of sulfur dioxide. Additionally, diethoxydiarylsilanes are suitable under the conditions as well.

  据报道，由乙酸铜（II）催化的三乙氧基硅烷，二氧化硫和肼的三组分反应，导致N-氨基磺酰胺的收率很高。在二氧化硫的插入过程中，不仅三乙氧基（芳基）硅烷而且三乙氧基（烷基）硅烷均相容。另外，二乙氧基二芳基硅烷在该条件下也是合适的。
• A palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines
  作者：Yuanyuan An、Hongguang Xia、Jie Wu

  DOI：10.1039/c5ob02514a

  日期：——

  nonaflates, sulfur dioxide, and hydrazines is reported. This transformation proceeds in the presence of Pd(OAc)2/XantPhos, and TBAB in 1,4-dioxane at 80 °C, leading to the corresponding N-aminosulfonamides in moderate to good yields. The reaction scope has been demonstrated, and good functional tolerance is observed. A plausible mechanism is proposed through the insertion of sulfur dioxide.

  据报道，通过钯催化的芳基壬二酸酯，二氧化硫和肼的偶联反应，可以容易地合成N-氨基磺酰胺。该转变在80°C下于1,4-二恶烷中的Pd（OAc）2 / XantPhos和TBAB存在下进行，从而以中等至良好的收率得到相应的N-氨基磺酰胺。已经证明了反应范围，并且观察到良好的功能耐受性。通过插入二氧化硫提出了一种合理的机制。
• Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium Salts with Sulfur Dioxide and Hydrazines
  作者：Nai-Wei Liu、Shuai Liang、Georg Manolikakes

  DOI：10.1002/adsc.201601341

  日期：2017.4.17

  three‐component synthesis of N‐aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy‐to‐handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium

  据报道，从二芳基碘鎓盐，肼和二氧化硫开始，光氧化还原催化的N-氨基磺酰胺的三组分合成。该反应在室温下在温和条件下进行，并由可见光驱动。可以使用简单的亚硫酸氢盐作为易于获得且易于处理的二氧化硫源。机理研究支持以二芳基碘鎓盐为芳基自由基的便捷来源的催化光氧化还原途径。
• Metal-Free Aminosulfonylation of Aryldiazonium Tetrafluoroborates with DABCO⋅(SO₂)₂and Hydrazines
  作者：Danqing Zheng、Yuanyuan An、Zhenhua Li、Jie Wu

  DOI：10.1002/anie.201309851

  日期：2014.2.24

  The coupling of aryldiazonium tetrafluoroborates, DABCO⋅(SO2)2, and hydrazines under metal‐free conditions leads to the formation of aryl N‐aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional‐group tolerance. A radical process is proposed for this transformation.

  四氟硼酸芳基重氮鎓，DABCO⋅（SO 2）2和肼在无金属条件下的偶联导致形成芳基N-氨基磺酰胺。反应在室温下平稳进行，并显示出宽泛的官能团耐受性。为此，提出了一个彻底的过程。
• Aminosulfonylation of aromatic amines, sulfur dioxide and hydrazines
  作者：Danqing Zheng、Ying Li、Yuanyuan An、Jie Wu

  DOI：10.1039/c4cc03032j

  日期：——

  A facile route to aryl N-aminosulfonamides under mild conditions is provided. The reaction of aromatic amines (including heteroaromatic amines), sulfur dioxide, and hydrazines proceeds efficiently with good functional group tolerance. The in situ generated diazonium ion is involved in the aminosulfonylation process.

  提供了在温和条件下制备芳基N-氨基磺酰胺的简便方法。芳族胺（包括杂芳族胺），二氧化硫和肼的反应以良好的官能团耐受性高效进行。原位产生的重氮离子参与氨基磺酰化过程。