2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)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-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane
• 英文别名: N-[2-bromo-1-(4-methylphenyl)ethyl]-4-methylbenzenesulfonamide
• 化学式: C₁₆H₁₈BrNO₂S
• 分子量: 368.294
• InChiKey: XRXOLTCJTNSJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Alpha-甲基苯乙烯 、 bromamine T 在 二氧化碳 作用下， 以 苯 为溶剂， 20.0 ℃ 、3.04 MPa 条件下， 反应 5.0h， 以86%的产率得到2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane
  参考文献：
  名称：

  CO2-induced amidobromination of olefins with bromamine-T

  摘要：

  描述了二氧化碳（CO2）诱导的与溴氨-T的烯烃胺基溴化反应。该方法可用于多种烯烃的反应，包括芳香烯烃和脂肪烯烃，以及富电子和缺电子的烯烃，从而区域选择性地形成胺基溴化化合物。

  DOI：

  10.1039/b923253m

文献信息

• Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions
  申请人：Doyle Michael P.

  公开号：US20090093638A1

  公开（公告）日：2009-04-09

  The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.

  本发明涉及在水相条件下实现有机分子的高效烯丙基氧化的组合物和方法，特别是烯烃和类固醇。该发明涉及使用二铑（II,II）“桨轮”配合物，特别是二铑羧酸酯和叔丁基过氧化氢作为催化剂进行反应。在烯丙基氧化7-酮类固醇中使用水相条件特别有优势，无法使用无水方法有效氧化，以及将烯丙基氧化扩展到烯酰胺和烯醇醚。
• 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。
• Hypervalent iodine-mediated aminobromination of olefins in water
  作者：Xue-Liang Wu、Guan-Wu Wang

  DOI：10.1016/j.tet.2009.08.069

  日期：2009.10

  The PhI(OAc)2-catalyzed aminobromination of electron-deficient olefins has been achieved in pure water with TsNH2 and NBS as nitrogen and bromine sources, respectively. With a catalytic amount of PhI(OAc)2, various olefins including α,β-unsaturated ketones, cinnamates, and cinnamides could be aminobrominated efficiently, giving the vicinal bromoamines in good yields and high regio- and diastereoselectivities

  在纯水中分别用TsNH 2和NBS作为氮源和溴源，已实现了PhI（OAc）2催化的缺电子烯烃的氨基溴化反应。用催化量的PhI（OAc）2，可以有效地将各种烯烃（包括α，β-不饱和酮，肉桂酸酯和肉桂酰胺）进行氨基溴化反应，从而使邻位溴胺的收率高，区域和非对映选择性高。以水为溶剂对于催化实现这种氨基溴化反应至关重要。在目前的水性条件下，苯乙烯的氨基溴化的区域选择性也大大提高了。
• Bromosulfonamidation of Alkenes using S,S-Dimethyl-N-(p-toluenesulfonyl)sulfilimine
  作者：Sadagopan Raghavan、S. Ramakrishna Reddy、K. A. Tony、Ch. Naveen Kumar、S. Nanda

  DOI：10.1055/s-2001-14910

  日期：——

  A new method for the bromosulfonamidation of olefins using a combination of S,S-dimethyl-N-(p-toluenesulfonyl)sulfilimine and N-bromosuccinimide is disclosed herein.

  本文公开了一种新的烯烃溴磺酰胺化方法，该方法结合了S，S-二甲基-N-(对甲苯磺酰)亚磺酰亚胺和N-溴代琥珀酰亚胺。
• 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.