N-(4-bromophenyl)-2-oxo-2-phenylethanesulfonamide | 1206688-39-2

• 英文名称: N-(4-bromophenyl)-2-oxo-2-phenylethanesulfonamide
• CAS: 1206688-39-2
• 化学式: C₁₄H₁₂BrNO₃S
• 分子量: 354.224
• InChiKey: ZSEHINTYMRAFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-2-oxo-2-phenylethanesulfonamide 在 Ru(OTf)(TsDPEN)(η6-p-cymene) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、4.05 MPa 条件下， 反应 24.0h， 以96%的产率得到(S)-N-(4-bromophenyl)-2-hydroxy-2-phenylethanesulfonamide
  参考文献：
  名称：

  手性阳离子钌二胺催化剂对β-酮磺酰胺和β-酮砜的不对称加氢反应

  摘要：

  AbstractOptically active β‐hydroxy sulfonamides and β‐hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of β‐keto sulfonamides and β‐keto sulfones has been developed using the phosphine‐free chiral ruthenium complex Ru(OTf)(TsDPEN)(η6‐p‐cymene) as the catalyst, to afford the corresponding β‐hydroxy sulfonamides and β‐hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic β‐keto sulfonamides and β‐keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic β‐hydroxy sulfonamides and β‐hydroxy sulfones in good yields with excellent enantio‐ and diastereoselectivities.magnified image

  DOI：

  10.1002/adsc.201300331

文献信息

• Highly enantioselective synthesis of β-hydroxysulfonamides by asymmetric transfer hydrogenation
  作者：Zhicong Geng、Yun Wu、Shifeng Miao、Zongxuan Shen、Yawen Zhang

  DOI：10.1016/j.tetlet.2010.12.054

  日期：2011.2

  A series of optically active β-hydroxy sulfonamides were synthesized for the first time by asymmetric transfer hydrogenation of the corresponding β-ketosulfonamides using the Ru–TsDPEN–HCOOH–Et3N catalytic system, in excellent yields (up to 95%) with excellent diastereo- (up to > 99:1 dr) and enantioselectivities (up to >99% ee).

  通过使用Ru–TsDPEN–HCOOH–Et 3 N催化系统，通过相应的β-酮磺酰胺的不对称转移加氢，首次合成了一系列旋光性β-羟基磺酰胺，具有优异的收率（高达95％）和优异的收率。非对映异构体（高达> 99：1 dr）和对映选择性（高达> 99％ee）。