(R)-N-(2-(4-chlorophenyl)-2-phenylethyl)-4-methylbenzenesulfonamide | 1612263-36-1

• 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: (R)-N-(2-(4-chlorophenyl)-2-phenylethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(2R)-2-(4-chlorophenyl)-2-phenylethyl]-4-methylbenzenesulfonamide
• CAS: 1612263-36-1
• 化学式: C₂₁H₂₀ClNO₂S
• 分子量: 385.914
• InChiKey: IYJXWJQTFHRKLR-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (S)-2-(4-chlorophenyl)-1-tosylaziridine 、 苯硼酸 在 (1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloro(3-phenylallyl)palladium(II) 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 以75%的产率得到(R)-N-(2-(4-chlorophenyl)-2-phenylethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki–Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives

  摘要：

  A palladium-catalyzed stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines with arylboronic acids under mild conditions to construct a tertiary stereogenic center has been developed. N-heterocyclic carbene (NHC) ligands efficiently promote the coupling, suppressing β-hydride elimination. The enantiospecific cross-coupling allowed us for preparation of a series of biologically important 2-arylphenethylamine derivatives in an enantiopure form.

  DOI：

  10.1021/ja5039616

文献信息

• Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
  作者：Brian P. Woods、Manuel Orlandi、Chung-Yang Huang、Matthew S. Sigman、Abigail G. Doyle

  DOI：10.1021/jacs.7b03448

  日期：2017.4.26

  to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

  报道了一种 Ni 催化的苯乙烯基氮丙啶与芳基碘化物的还原交叉偶联。该反应通过立体会聚机制进行，因此适用于使用 Ni 的手性生物恶唑啉配体进行不对称催化。该过程允许从外消旋氮丙啶轻松获得高度对映体富集的 2-芳基苯乙胺。多变量分析表明，配体极化率等特征会影响观察到的对映选择性，揭示了这种新兴配体类别在对映选择性 Ni 催化方面的成功。
• Correction to “Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines”
  作者：Brian P. Woods、Manuel Orlandi、Chung-Yang Dennis Huang、Matthew S. Sigman、Abigail G. Doyle

  DOI：10.1021/jacs.8b05650

  日期：2018.6.20
• Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki–Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives
  作者：Youhei Takeda、Yuki Ikeda、Akinobu Kuroda、Shino Tanaka、Satoshi Minakata

  DOI：10.1021/ja5039616

  日期：2014.6.18

  A palladium-catalyzed stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines with arylboronic acids under mild conditions to construct a tertiary stereogenic center has been developed. N-heterocyclic carbene (NHC) ligands efficiently promote the coupling, suppressing β-hydride elimination. The enantiospecific cross-coupling allowed us for preparation of a series of biologically important 2-arylphenethylamine derivatives in an enantiopure form.