1,8-diamino-3-thia-6-azaoctane | 19030-85-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,8-diamino-3-thia-6-azaoctane
• 英文别名: N'-[2-(2-aminoethylsulfanyl)ethyl]ethane-1,2-diamine
• CAS: 19030-85-4
• 化学式: C₆H₁₇N₃S
• 分子量: 163.287
• InChiKey: GMEYOVDUFLBZLP-UHFFFAOYSA-N

物化性质

• 沸点：
  120-126 °C(Press: 0.4-0.8 Torr)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  10
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  89.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氨乙基硫醚 、 2-溴乙胺氢溴酸盐 在 cesium hydroxide 、 4 A molecular sieve 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以73%的产率得到1,8-diamino-3-thia-6-azaoctane
  参考文献：
  名称：

  铯效应：在胺的直接N-烷基化反应中具有很高的化学选择性。

  摘要：

  为了有效地制备仲胺，使用铯碱开发了一种用于伯胺，二胺和多胺的单N-烷基化的新方法。铯碱不仅促进伯胺的烷基化，而且抑制产生的仲胺的过度烷基化。检查了各种胺，烷基溴化物和烷基磺酸盐，结果表明该方法具有较高的化学选择性，比单烷基化更有利于单-N-烷基化。特别地，使用空间要求高的底物或氨基酸衍生物可专门提供仲胺，在拟肽合成中具有广泛的应用。

  DOI：

  10.1021/jo010643c

文献信息

• CsOH-promoted chemoselective mono-N-alkylation of diamines and polyamines
  作者：Ralph N Salvatore、Shaun E Schmidt、Seung Il Shin、Advait S Nagle、Jay H Worrell、Kyung Woon Jung

  DOI：10.1016/s0040-4039(00)01747-0

  日期：2000.12

  Selective N-alkylation of diamines and polyamines was carried out using cesium hydroxide, 4 Angstrom molecular sieves, and DMF. This protocol was highly chemoselective, favoring mono-N-alkylation over overalkylations. (C) 2000 Published by Elsevier Science Ltd.
• US6423871B1
  申请人：——

  公开号：US6423871B1

  公开（公告）日：2002-07-23
• [EN] EFFICIENT SYNTHESIS OF SECONDARY AMINES BY SELECTIVE ALKYLATION OF PRIMARY AMINES<br/>[FR] SYNTHESE EFFICACE D'AMINES SECONDAIRES PAR ALKYLATION SELECTIVE D'AMINES PRIMAIRES
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2000050377A1

  公开（公告）日：2000-08-31

  A method for selective mono-N-alkylation of primary amines to produce secondary amines that are substantially free of overalkylated tertiary amines and quaternary ammonium salts, under mild reaction conditions without the necessity of protecting groups. Compounds of the class of secondary amines are produced by reacting an alkyl halide with an alkyl amine in anhydrous solvent, preferably dimethyl sulfoxide or N,N-dimethylformamide, in the presence of 0.1 to 3 molar equivalents of a cesium base. Optionally, the extent and selectivity of mono-N-alkylation is enhanced by addition to the reaction mixture of a powdered molecular sieve material for removal of water produced by the reaction, and/or tetrabutylammonium iodide to promote halide exchange. The invention permits selective and efficient mono-N-alkylation of a wide variety of substrates at 23 °C; does not cause racemization when used with enantiomerically-pure chiral substrates such as L-α-aminoesters; and is applied to solid phase synthesis whereby either the alkyl amine or alkyl halide is immobilized. The method is additionally used to produce polyamines, such as N-(2-(2-aminoethylthio)ethyl)ethylenediamine in 73 % yield.
• Cesium Effect:  High Chemoselectivity in Direct N-Alkylation of Amines
  作者：Ralph Nicholas Salvatore、Advait S. Nagle、Kyung Woon Jung

  DOI：10.1021/jo010643c

  日期：2002.2.1

  A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this

  为了有效地制备仲胺，使用铯碱开发了一种用于伯胺，二胺和多胺的单N-烷基化的新方法。铯碱不仅促进伯胺的烷基化，而且抑制产生的仲胺的过度烷基化。检查了各种胺，烷基溴化物和烷基磺酸盐，结果表明该方法具有较高的化学选择性，比单烷基化更有利于单-N-烷基化。特别地，使用空间要求高的底物或氨基酸衍生物可专门提供仲胺，在拟肽合成中具有广泛的应用。