(S)-4-methyl-N-(3-methyl-1-(phenylthio)butan-2-yl)benzenesulfonamide

• 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: (S)-4-methyl-N-(3-methyl-1-(phenylthio)butan-2-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(2S)-3-methyl-1-phenylsulfanylbutan-2-yl]benzenesulfonamide
• 化学式: C₁₈H₂₃NO₂S₂
• 分子量: 349.518
• InChiKey: FRDVELPDSILIFI-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S)-2-isopropyl-1-[(4-methylphenyl)sulfonyl]aziridine 、 二苯二硫醚 在 盐酸 、 锌 作用下， 以 水 为溶剂， 反应 1.5h， 以70%的产率得到(S)-4-methyl-N-(3-methyl-1-(phenylthio)butan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of chiral β-chalcogen amine derivatives and Gram-positive bacteria activity

  摘要：

  Efficient ring opening reaction between aziridines and diphenyl dichalogenides using HCl, Zn degrees in ionic liquid is disclosed, affording chiral beta-chalcogen amines derivatives in good yields under mild reaction condition. The ionic liquid was further reused four times without the loss of its efficiency. The chiral chalcogenoamines showed antimicrobial activity against Gram-positive bacteria strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.049

文献信息

• Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
  作者：James C. Anderson、Rachel Cubbon、Michael Harding、Daniel S. James

  DOI：10.1016/s0957-4166(98)00344-9

  日期：1998.10

  A series of new chiral sulfur-nitrogen chelate ligands, derived from amino acids, has been synthesised rationally. Fruitless experiments into catalytic asymmetric conjugate additions and desymmetrisation of meso-epoxides led us to analyse our ligands in the catalytic asymmetric addition of diethylzinc to aromatic aldehydes. These latter experiments were successful with chiral benzylic alcohols being obtained in up to 82% enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of chiral β-chalcogen amine derivatives and Gram-positive bacteria activity
  作者：Josimar Vargas、Senthil Narayanaperumal、Kashif Gul、Bruno B. Ravanello、Luciano Dornelles、Letiere C. Soares、Camilla F.S. Alves、Taiane Schneider、Rodrigo de A. Vaucher、Roberto C.V. Santos、Oscar E.D. Rodrigues

  DOI：10.1016/j.tet.2012.09.049

  日期：2012.12

  Efficient ring opening reaction between aziridines and diphenyl dichalogenides using HCl, Zn degrees in ionic liquid is disclosed, affording chiral beta-chalcogen amines derivatives in good yields under mild reaction condition. The ionic liquid was further reused four times without the loss of its efficiency. The chiral chalcogenoamines showed antimicrobial activity against Gram-positive bacteria strains. (C) 2012 Elsevier Ltd. All rights reserved.