Toluene-4-sulfonic acid; compound with (E)-3-phenyl-allylamine | 146287-09-4

• 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: Toluene-4-sulfonic acid; compound with (E)-3-phenyl-allylamine
• 英文别名: 4-methylbenzenesulfonic acid;3-phenylprop-2-en-1-amine
• CAS: 146287-09-4
• 化学式: C₇H₈O₃S*C₉H₁₁N
• 分子量: 305.398
• InChiKey: DRRFSKWVMRBYJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肉桂醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 Toluene-4-sulfonic acid; compound with (E)-3-phenyl-allylamine
  参考文献：
  名称：

  NEW PROTOCOL FOR CONVERTING ALCOHOLS INTO AMINES

  摘要：

  The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1. diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.

  DOI：

  10.1081/scc-100103987

文献信息

• Optimized Procedures for One-Pot Conversion of Alkyl Bromides into Amines via the Staudinger Reaction
  作者：Anna Koziara、Andrzej Zwierzak

  DOI：10.1055/s-1992-26300

  日期：——

  New optimized procedures for transforming primary and secondary alkyl bromides into the corresponding primary amine salts have been elaborated. Essential modifications of azidation and deprotection of intermediate triethoxyphosphine alkylimides resulted in substantial improvement of the overall yields. Conversion of ammonium tosylates and hydrochlorides into free amines in a non-aqueous medium is described.

  新的优化程序已详细阐述，用于将伯和仲烷基溴转化为相应的伯胺盐。通过对叠氮化和中间体三乙氧基膦烷基亚胺的去保护进行必要修改，总体产率得到了显著提高。还在非水介质中描述了将对甲苯磺酸铵盐和盐酸盐转化为游离胺的过程。
• An Optimized Version of Gabriel-Type Nucleophilic Amination
  作者：Andrzej Zwierzak

  DOI：10.1080/00397910008086868

  日期：2000.7

  N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t-butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-1. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol affords ammonium tosylates 3a-1 in reasonable yields.