1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine | 141666-87-7

• 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: 1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine
• 英文别名: 1-Tosyl-1-[2-(4-methoxyphenyl)ethyl]hydrazine；N-[2-(4-methoxyphenyl)ethyl]-4-methylbenzenesulfonohydrazide
• CAS: 141666-87-7
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: AGCIDRCPZAIQMU-UHFFFAOYSA-N

物化性质

• 沸点：
  497.6±55.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine 在 氢氧化钾 、 乙醇 、 氧气 作用下， 以98%的产率得到对甲氧基苯乙醇
  参考文献：
  名称：

  Base-promoted oxygenation of N-substituted-N-tosylhydrazines -- a convenient route to hydroxydeamination of primary amines

  摘要：

  Treatment of 1-substituted-1-tosylhydrazines with KOH in refluxing ethanol in the presence of atmospheric oxygen affords the corresponding alcohols in high yield. This reaction, proceeding via ethanol reduction of an intermediate hydroperoxide, provides a convenient route to hydroxydeamination of primary amines.

  DOI：

  10.1016/s0040-4039(00)60796-7
• 作为产物：
  描述：

  N-十二烷基对甲苯磺酰胺 在 N-氯代丁二酰亚胺 、 2,4-二硝基苯基羟胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine
  参考文献：
  名称：

  A convenient conversion of primary amines into the corresponding halides — Radical promoted halodeamination via N-substituted-N-Tosylhydrazines

  摘要：

  DOI：

  10.1016/0040-4039(94)80009-x

文献信息

• Convenient halodeamination and hydrodeamination of primary amines.
  作者：Frank S. Guziec、Dongchu Wei

  DOI：10.1021/jo00040a010

  日期：1992.7

  Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.
• Conversion of N-substituted N-sulfonylhydrazines into hydroperoxides - a new synthetic route to hydroperoxides via hydroperoxydeamination
  作者：Luis Collazo、Frank S. Guziec、Wei Xiao Hu、Antonio Munoz、Dongchu Wei、Migdalia Alvarado

  DOI：10.1021/jo00075a003

  日期：1993.11

  N-Substituted N-sulfonylhydrazines, obtained by amination of primary amine sulfonamides, can be readily oxygenated by atmospheric oxygen under basic conditions below room temperature to cleanly afford alkyl hydroperoxides in good yield.
• A convenient conversion of primary amines into the corresponding halides — Radical promoted halodeamination via N-substituted-N-Tosylhydrazines
  作者：Luis R. Collazo、Frank S. Guziec、Wei-Xiao Hu、Ratnadevi Pankayatselvan

  DOI：10.1016/0040-4039(94)80009-x

  日期：1994.10
• Base-promoted oxygenation of N-substituted-N-tosylhydrazines -- a convenient route to hydroxydeamination of primary amines
  作者：Frank S. Guziec、Dongchu Wei

  DOI：10.1016/s0040-4039(00)60796-7

  日期：——

  Treatment of 1-substituted-1-tosylhydrazines with KOH in refluxing ethanol in the presence of atmospheric oxygen affords the corresponding alcohols in high yield. This reaction, proceeding via ethanol reduction of an intermediate hydroperoxide, provides a convenient route to hydroxydeamination of primary amines.