N-(1-{N'-[2-{4-methylbenzenesulfonylamino}-3-methyl-pentyl]aminomethyl}-2-methylbutyl)-4-methylbenzenesulfonamide | 460743-54-8

• 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-(1-{N'-[2-{4-methylbenzenesulfonylamino}-3-methyl-pentyl]aminomethyl}-2-methylbutyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(2S)-1-[benzyl-[(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]pentyl]amino]-3-methylpentan-2-yl]-4-methylbenzenesulfonamide
• CAS: 460743-54-8
• 化学式: C₃₃H₄₇N₃O₄S₂
• 分子量: 613.886
• InChiKey: QLTGUYFEEKITEE-XRGPIXSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1-{N'-[2-{4-methylbenzenesulfonylamino}-3-methyl-pentyl]aminomethyl}-2-methylbutyl)-4-methylbenzenesulfonamide 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 以95%的产率得到(2S,6S)-1,7-di-p-toluenesulfonyl-2,6-di(1-methylpropyl)-1,4,7-triazaheptane
  参考文献：
  名称：

  衍生自手性氮丙啶的C 2对称的1,4,7-三氮杂环壬烷配体的合成

  摘要：

  从手性池合成1,4,7-三氮杂环壬烷14的C 2对称衍生物的有效合成路线氨基酸已经被开发出来。这些调查表明，哌嗪 当使用不合适的氮保护基团时，发生7。显然，哌嗪发生分子内亲核攻击并随后消除β的结果。这似乎仅与[9] -N 3环的形成有关，因为较大的[12] -N 4 大循环，11，是通过Richman–Atkins环化反应在相同的苄基保护下形成的氮原子。单晶的X射线结构哌嗪 7a和1,4,7-三氮杂环壬烷14a都表明，在这些系统中，弱分子间C–H⋯O S相互作用以固态发生。

  DOI：

  10.1039/b204818c
• 作为产物：
  描述：

  苄胺 、 (S)-2-((R)-sec-butyl)-1-tosylaziridine 以 甲醇 为溶剂， 反应 72.0h， 以79%的产率得到N-(1-{N'-[2-{4-methylbenzenesulfonylamino}-3-methyl-pentyl]aminomethyl}-2-methylbutyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Solvent-mediated selective single and double ring-opening of N-tosyl-activated aziridines using benzylamine

  摘要：

  An efficient methodology has been developed for the synthesis of a series of new diamine 2 and triamine ligands 3 for application in asymmetric catalysis via selective single or double ring-opening of tosylaziridines 1, which are derived from chiral pool amino acids. The selectivity of the ring-opening reaction is readily controlled by the solvent employed. Thus, in acetonitrile formation of secondary amines 2 occurs via a single ring-opening step. whilst in methanol the reactions proceed to give the tertiary amines 3 via the ring-opening of two aziridine molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00102-7

文献信息

• Solvent-mediated selective single and double ring-opening of N-tosyl-activated aziridines using benzylamine
  作者：J.Erik W. Scheuermann、Gennadiy Ilyashenko、D.Vaughan Griffiths、Michael Watkinson

  DOI：10.1016/s0957-4166(02)00102-7

  日期：2002.3

  An efficient methodology has been developed for the synthesis of a series of new diamine 2 and triamine ligands 3 for application in asymmetric catalysis via selective single or double ring-opening of tosylaziridines 1, which are derived from chiral pool amino acids. The selectivity of the ring-opening reaction is readily controlled by the solvent employed. Thus, in acetonitrile formation of secondary amines 2 occurs via a single ring-opening step. whilst in methanol the reactions proceed to give the tertiary amines 3 via the ring-opening of two aziridine molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The synthesis of C2-symmetric 1,4,7-triazacyclononane ligands derived from chiral aziridines
  作者：J. Erik W. Scheuermann、Fiona Ronketti、Majid Motevalli、D. Vaughan Griffiths、Michael Watkinson

  DOI：10.1039/b204818c

  日期：2002.7.24

  An efficient synthetic route for the synthesis of C2-symmetric derivatives of 1,4,7-triazacyclononanes 14 from chiral pool amino acids has been developed. These investigations have shown that competitive formation of piperazines 7 occurs when inappropriate nitrogen protecting groups are employed. It is apparent that the formation of the piperazines occurs as a result of an intramolecular nucleophilic

  从手性池合成1,4,7-三氮杂环壬烷14的C 2对称衍生物的有效合成路线氨基酸已经被开发出来。这些调查表明，哌嗪 当使用不合适的氮保护基团时，发生7。显然，哌嗪发生分子内亲核攻击并随后消除β的结果。这似乎仅与[9] -N 3环的形成有关，因为较大的[12] -N 4 大循环，11，是通过Richman–Atkins环化反应在相同的苄基保护下形成的氮原子。单晶的X射线结构哌嗪 7a和1,4,7-三氮杂环壬烷14a都表明，在这些系统中，弱分子间C–H⋯O S相互作用以固态发生。