(2S,2'S)-1,1'-di-(4-methylbenzenesulfonyl)-2,2'-biaziridine

• 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: (2S,2'S)-1,1'-di-(4-methylbenzenesulfonyl)-2,2'-biaziridine
• 英文别名: (2S)-1-(4-methylphenyl)sulfonyl-2-[(2S)-1-(4-methylphenyl)sulfonylaziridin-2-yl]aziridine
• 化学式: C₁₈H₂₀N₂O₄S₂
• 分子量: 392.5
• InChiKey: BSHBOPSHAUCSFY-VCAKUFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-1,1'-di-(4-methylbenzenesulfonyl)-2,2'-biaziridine 在 copper(l) iodide 、 copper(I) bromide dimethylsulfide complex 、 cesium acetate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 88.0h， 生成 (2S,2'S)-1,1'-ditosyl-1,1',2,2',3,3',4,4'-octahydro-2,2'-biquinoline
  参考文献：
  名称：

  Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines

  摘要：

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.

  DOI：

  10.1021/ol502164b
• 作为产物：
  描述：

  [(2R,3R)-1,4-bis[(4-methylphenyl)sulfonylamino]-3-methylsulfonyloxybutan-2-yl] methanesulfonate 在 potassium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 12.0h， 生成 (2S,2'S)-1,1'-di-(4-methylbenzenesulfonyl)-2,2'-biaziridine
  参考文献：
  名称：

  Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines

  摘要：

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.

  DOI：

  10.1021/ol502164b

文献信息

• Chemistry of Tetrathiomolybdate:  Aziridine Ring Opening Reactions and Facile Synthesis of Interesting Sulfur Heterocycles
  作者：Devarajulu Sureshkumar、Srinivasa Murthy Koutha、Srinivasan Chandrasekaran

  DOI：10.1021/ja052969z

  日期：2005.9.1

  [BnEt3N]2MoS4, has been used successfully to effect ring opening of aziridines in a regiospecific and stereospecific manner under mild reaction conditions without the use of Lewis acid catalyst. Utility of this reagent in tandem and multistep processes in a one-pot operation for the synthesis of various novel sulfur heterocycles in very good yield is also reported.

  四硫代钼酸苄基三乙基铵 [BnEt3N]2MoS4 已成功用于在温和的反应条件下以区域专一性和立体专一性方式实现氮丙啶的开环，无需使用路易斯酸催化剂。还报道了该试剂在一锅操作中以串联和多步方法合成各种新型硫杂环的用途，产率非常好。
• Alkylating agents related to 2,2'-biaziridine. III. Stereoisomeric N,N'-dimethylsulfonyl-2,2'-biaziridines
  作者：Peter W. Feit、Ole T. Nielsen

  DOI：10.1021/jm00297a025

  日期：1970.5
• Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
  作者：Stephen J. Bailey、Steven M. Wales、Anthony C. Willis、Paul A. Keller

  DOI：10.1021/ol502164b

  日期：2014.8.15

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.