((1S)-1-{[benzyl((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]methyl}-2-methylpropyl)-4-methylbenzenesulfonamide | 460743-50-4

• 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: ((1S)-1-{[benzyl((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]methyl}-2-methylpropyl)-4-methylbenzenesulfonamide
• 英文别名: N-(1-{N'-benzyl-N'-[2-{4-methylbenzenesulfonylamino}-3-methyl-butyl]aminomethyl}-2-methyl-propyl)-4-methylbenzenesulfonamide；N-[(2S)-1-[benzyl-[(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl]amino]-3-methylbutan-2-yl]-4-methylbenzenesulfonamide
• CAS: 460743-50-4
• 化学式: C₃₁H₄₃N₃O₄S₂
• 分子量: 585.832
• InChiKey: GYOPATJHFJWRTN-FIRIVFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  ((1S)-1-{[benzyl((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]methyl}-2-methylpropyl)-4-methylbenzenesulfonamide 在 palladium dihydroxide 吡啶 、 盐酸 、 氨 、 氢气 、 lithium 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (2S,6S)-2,6-di(1-methylethyl)-1,4,7-triazacyclononane
  参考文献：
  名称：

  手性1,4,7-三氮杂环壬烷的合成

  摘要：

  描述了用于合成手性环环状2，6-二取代的1,4,7-三甲基-1,4,7-三氮杂大环的新颖且灵活的途径。只要将N，N-双-[2-（甲苯-磺酰氨基）乙基]-甲苯-4-磺酰胺的手性类似物用作亲核组分，就可以实现有效的大环化。由这些2,6-二取代的1,4,7-三甲基-1,4,7-三氮杂大环与锰（II）原位制备的配合物催化了苯乙烯与过氧化氢的不对称环氧化。

  DOI：

  10.1016/s0040-4039(02)00705-0
• 作为产物：
  描述：

  (2S)-2-isopropyl-1-[(4-methylphenyl)sulfonyl]aziridine 、 苄胺 以 甲醇 为溶剂， 反应 72.0h， 以75%的产率得到((1S)-1-{[benzyl((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]methyl}-2-methylpropyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  手性双环胍：简洁高效的基于氮丙啶的合成

  摘要：

  使用简洁有效的基于氮丙啶的合成方法合成了一系列对称或不对称的手性双环胍。从商业氨基醇开始，进行了五个合成步骤，仅三个步骤需要进行色谱纯化，以43-71％的总收率得到所需的胍。使用这些胍的初步研究表明，对几种迈克尔反应具有中等对映选择性。

  DOI：

  10.1016/j.tetlet.2005.11.133

文献信息

• The synthesis of chiral annulet 1,4,7-triazacyclononanes
  作者：Gilles Argouarch、Colin L Gibson、Graham Stones、David C Sherrington

  DOI：10.1016/s0040-4039(02)00705-0

  日期：2002.5

  Novel and flexible routes for the synthesis of chiral ring annulet 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles are described. Efficient macrocyclisations were realised provided that chiral analogues of N,N-bis-[2-(toluene-sulfonylamino)ethyl]-toluene-4-sulfonamide were used as the nucleophilic components. Complexes prepared, in situ, from these 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles

  描述了用于合成手性环环状2，6-二取代的1,4,7-三甲基-1,4,7-三氮杂大环的新颖且灵活的途径。只要将N，N-双-[2-（甲苯-磺酰氨基）乙基]-甲苯-4-磺酰胺的手性类似物用作亲核组分，就可以实现有效的大环化。由这些2,6-二取代的1,4,7-三甲基-1,4,7-三氮杂大环与锰（II）原位制备的配合物催化了苯乙烯与过氧化氢的不对称环氧化。
• 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。
• Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde
  作者：Fredrik Lake、Christina Moberg

  DOI：10.1002/1099-0690(200209)2002:18<3179::aid-ejoc3179>3.0.co;2-a

  日期：——

  A modular approach was developed for the preparation of chiral, enantiopure sulfonamide ligands with C-1, C-2, and C-3 symmetry by ring opening of chiral N-sulfonylaziridines with ammonia, primary amines, and diamines. The new ligands were assessed in the titanium-mediated addition of diethylzinc to benzaldehyde, giving the product with selectivities up to 76% ee. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
• 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.
• Bifurcated, modular syntheses of chiral annulet triazacyclononanes
  作者：Gilles Argouarch、Graham Stones、Colin L. Gibson、Alan R. Kennedy、David C. Sherrington

  DOI：10.1039/b310492c

  日期：——

  Three chiral 2,6-disubstituted tri-N-methyl azamacrocycles have been prepared by modular methods. These macrocycles were accessed from three chiral 1,4,7-triazaheptanes intermediates that were prepared by two independent routes. The first of these routes involved the benzylamine opening of chiral tosyl aziridines followed by debenzylation but was problematic on solubility grounds. A second, more effective, route was developed which avoided debenzylation by using ammonia in the nucleophilic opening of chiral tosyl aziridines.

  通过模块化方法合成了三种手性2,6-二取代的三-N-甲基氮杂大环。这些大环是通过两条独立路线合成的三种手性1,4,7-三氮七烷中间体获得的。第一条路线涉及手性磺酰氮杂环丁烷的苄胺开环，随后进行去苄基化，但在溶解性方面存在问题。第二条更有效的路线则采用氨在手性磺酰氮杂环丁烷的亲核开环中，避免了去苄基化。