(1S,2S)-N-p-styrenesulfonyl-1,2-diphenylethylenediamine | 200557-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-N-p-styrenesulfonyl-1,2-diphenylethylenediamine
• 英文别名: N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-ethenylbenzenesulfonamide
• CAS: 200557-69-3
• 化学式: C₂₂H₂₂N₂O₂S
• 分子量: 378.495
• InChiKey: LCTBXWDGOUJPOR-VXKWHMMOSA-N

物化性质

• 沸点：
  557.140±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.225±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium p-styrenesulfonate 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (1S,2S)-N-p-styrenesulfonyl-1,2-diphenylethylenediamine
  参考文献：
  名称：

  Superhydrophobic, chiral, and mesoporous TsDPEN copolymer coordinated to ruthenium species as an efficient catalyst for asymmetric transfer hydrogenation

  摘要：

  Homogeneous chiral catalysts usually show higher catalytic activities than corresponding heterogeneous chiral catalysts, because of their easy interaction between catalytically active sites with reactant molecules. We demonstrate here superhydrophobic, chiral, and mesoporous catalysts (TsDPEN-Ru) synthesized from copolymerization of N-p-styrenesulfonyl-1,2-diphenylethylenediamine (V-TsDPEN) with divinylbenzene and loading of Ru species exhibiting much higher activities in asymmetric transfer hydrogenation (ATH) of ketones in aqueous solution than corresponding homogeneous chiral catalyst. This phenomenon is strongly related to the unique features of high enrichment for the reactants in superhydrophobic TsDPEN-Ru catalysts due to their good wettability, as well as easy transfer of product from the catalyst into water phase. These features open a door for design and developing a wide variety of chiral catalysts for asymmetric catalysis. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.nantod.2013.07.002

文献信息

• Preparation of microgel-supported chiral catalysts and their application in the asymmetric hydrogenation of aromatic ketones
  作者：Jia Deng、Cuifen Lu、Guichun Yang、Zuxing Chen

  DOI：10.1016/j.reactfunctpolym.2012.03.011

  日期：2012.6

  distinct microgel-supported chiral TsDPEN derivatives. These chiral copolymers were allowed to form complexes with [RuCl 2 (cymene)] 2 and the resulting homogeneous catalysts were applied in asymmetric hydrogenation reactions of aromatic ketones to give enantioenriched secondary alcohols in quantitative yield. These polymeric catalysts can be easily separated from the reaction mixture and recycled several

  摘要制备了对映体纯的手性单体（S，S）-2，并与苯乙烯和四种不同的交联剂共聚，生成了四种不同的微凝胶负载的手性TsDPEN衍生物。使这些手性共聚物与[RuCl 2（cymene）] 2形成络合物，并将所得的均相催化剂用于芳族酮的不对称氢化反应中，以定量收率得到对映体富集的仲醇。这些聚合物催化剂可以容易地从反应混合物中分离出来并循环使用几次，而催化活性没有明显损失。
• A pH-Responsive Soluble-Polymer-Based Homogeneous Ruthenium Catalyst for Highly Efficient Asymmetric Transfer Hydrogenation (ATH)
  作者：Yinzheng Xie、Mengpan Wang、Xiaohui Wu、Chen Chen、Wenbo Ma、Qifeng Dong、Mingming Yuan、Zhenshan Hou

  DOI：10.1002/cplu.201600062

  日期：2016.6

  acrylamide (DMAPA) and N-p-styrenesulfonyl-1,2-diphenylethylenediamine (V-TsDPEN). The pH-responsive polymer coordination ruthenium complex was thus prepared and employed as an efficient catalyst for the asymmetric transfer hydrogenation (ATH) of various ketones. The polymer catalyst exhibited an attractive pH-induced phase-separable behavior in water: it could be dissolved in water when the pH of the

  通过二甲基氨基丙基丙烯酰胺（DMAPA）和Np-苯乙烯磺酰基-1,2-二苯基乙二胺（V-TsDPEN）的共聚成功地合成了一种pH响应性聚合物。由此制备了pH响应性聚合物配位钌络合物，并用作各种酮的不对称转移氢化（ATH）的有效催化剂。聚合物催化剂在水中表现出有吸引力的pH诱导的相分离行为：当反应开始时溶液的pH值低于6.5时，它可以溶解在水中，而当溶液的pH值从水中完全沉淀出来时。反应后溶液高于8.5。另外，该催化剂对带有不同官能团的多种底物的ATH高效，并且可以通过自分离轻松地从水溶液中回收。它们可以回收八次，而催化活性和对映选择性没有明显变化。
• Halle, R.; Schulz, E.; Lemaire M., Synlett, 1997, # 11, p. 1257 - 1258
  作者：Halle, R.、Schulz, E.、Lemaire M.

  DOI：——

  日期：——