2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane

• 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: 2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane
• 英文别名: N-bromo-N-[2-bromo-1-(4-methylphenyl)ethyl]-4-methylbenzenesulfonamide
• 化学式: C₁₆H₁₇Br₂NO₂S
• 分子量: 447.19
• InChiKey: IVXGSIHVCBTRES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane 、 丁二酰亚胺 以 二氯甲烷-D2 为溶剂， 生成 N-溴代丁二酰亚胺(NBS) 、 2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane
  参考文献：
  名称：

  Efficient aziridination of olefins catalyzed by dirhodium catalysts

  摘要：

  这项发明涉及用于实现有机分子，特别是烯烃的高效环氮化的组合物和方法。更具体地，该发明涉及一种温和、选择性和高效的环氮化方案，涉及通过混合价二铑（II,III）催化剂（Rh25+）进行催化。特别偏好用于形成这种混合价二铑（II,III）催化剂（Rh25+）的来源是二铑（II）羧酰胺酸盐，例如二铑（II）己内酰胺酸盐，以及它们的衍生物和类似物。

  公开号：

  US20060211870A1
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 、 dibromamine-T 以 二氯甲烷 为溶剂， 生成 2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane
  参考文献：
  名称：

  Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate

  摘要：

  A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh-2(cap)(4)center dot 2CH(3)CN] is described. Use of p-toluenesulfonamide (TsNH2), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in isolated yields of up to 95% under extremely mild conditions with as little as 0.01 mol% Rh-2(cap)(4). Aziridine formation occurs through Rh-2(5+)-catalyzed aminobromination and subsequent base-induced ring closure. An X-ray crystal structure of a Rh-2(5+) halide complex, formed from the reaction between Rh-2(cap)(4) and N-chlorosuccinimide, has been obtained.

  DOI：

  10.1021/ol0510973

文献信息

• US7662969B2
  申请人：——

  公开号：US7662969B2

  公开（公告）日：2010-02-16
• Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate
  作者：Arthur J. Catino、Jason M. Nichols、Raymond E. Forslund、Michael P. Doyle

  DOI：10.1021/ol0510973

  日期：2005.6.1

  A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh-2(cap)(4)center dot 2CH(3)CN] is described. Use of p-toluenesulfonamide (TsNH2), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in isolated yields of up to 95% under extremely mild conditions with as little as 0.01 mol% Rh-2(cap)(4). Aziridine formation occurs through Rh-2(5+)-catalyzed aminobromination and subsequent base-induced ring closure. An X-ray crystal structure of a Rh-2(5+) halide complex, formed from the reaction between Rh-2(cap)(4) and N-chlorosuccinimide, has been obtained.
• Efficient aziridination of olefins catalyzed by dirhodium catalysts
  申请人：Doyle P. Michael

  公开号：US20060211870A1

  公开（公告）日：2006-09-21

  This invention relates to compositions and methods for achieving the efficient aziridination of organic molecules, especially olefins. More specifically, the invention is directed to a mild, selective, and efficient aziridination protocol that involves catalysis by a mixed-valent dirhodium(II,III) catalyst (Rh 2 5+ ). Especially preferred sources for forming such mixed-valent dirhodium(II,III) catalyst (Rh 2 5+ ) are dirhodium(II) carboxamidates, such as dirhodium(II) caprolactamate, and their derivatives and analogues.

  这项发明涉及用于实现有机分子，特别是烯烃的高效环氮化的组合物和方法。更具体地，该发明涉及一种温和、选择性和高效的环氮化方案，涉及通过混合价二铑（II,III）催化剂（Rh25+）进行催化。特别偏好用于形成这种混合价二铑（II,III）催化剂（Rh25+）的来源是二铑（II）羧酰胺酸盐，例如二铑（II）己内酰胺酸盐，以及它们的衍生物和类似物。