(R)-N-p-nitrobenzenesulfonyl-2-benzylaziridine | 648894-18-2

• 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: (R)-N-p-nitrobenzenesulfonyl-2-benzylaziridine
• 英文别名: (2R)-2-Benzyl-1-(4-nitrobenzene-1-sulfonyl)aziridine；(2R)-2-benzyl-1-(4-nitrophenyl)sulfonylaziridine
• CAS: 648894-18-2
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: IHLFUJIVYFFCNW-IURRXHLWSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  497.4±47.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-1-丁醇 、 (R)-N-p-nitrobenzenesulfonyl-2-benzylaziridine 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

  摘要：

  This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with omega-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically Pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.

  DOI：

  10.1021/jo900441s
• 作为产物：
  描述：

  D-苯丙氨醇 、 对硝基苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到(R)-N-p-nitrobenzenesulfonyl-2-benzylaziridine
  参考文献：
  名称：

  Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

  摘要：

  This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with omega-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically Pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.

  DOI：

  10.1021/jo900441s

文献信息

• Enantiospecific and regioselective opening of 2-alkyl nosylaziridines by indoles mediated by boron trifluoride. Application to a practical synthesis of a GnRH antagonist
  作者：Roger N Farr、Ramon J Alabaster、John Y.L Chung、Bridgette Craig、John S Edwards、Andrew W Gibson、Guo-Jie Ho、Guy R Humphrey、Simon A Johnson、E.J.J Grabowski

  DOI：10.1016/j.tetasy.2003.08.038

  日期：2003.11

  An efficient, high yield process for the synthesis of a GnRH antagonist has been developed. We have demonstrated that under boron trifluoride mediation, nosyl aziridines will react with 2-arylindole derivatives to afford β-substituted tryptamines in an enantiospecific process with remarkably high regioselectivity. The scope of the reaction was explored with several 2-substituted nosyl aziridines. The

  已经开发了用于合成GnRH拮抗剂的有效，高产率的方法。我们已经证明，在三氟化硼的介导下，壬基氮丙啶会与2-芳基吲哚衍生物反应，以对映特异性的方法提供具有高区域选择性的β-取代的色胺。用几种2-取代的壬基氮杂氮丙啶探索反应的范围。关键反应是为GnRH拮抗剂程序明确开发的，并已在40千克规模上得到证明。