(S)-4-methyl-N-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzenesulfonamide | 1159428-81-5

• 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-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(2S)-1-phenyl-3-phenylselanylpropan-2-yl]benzenesulfonamide
• CAS: 1159428-81-5
• 化学式: C₂₂H₂₃NO₂SSe
• 分子量: 444.456
• InChiKey: VYSXQGHVFROYQL-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  二苯基二硒醚 、 S)-(+)- 2-苄基- 1-（对甲苯磺酰）氮丙啶 在 盐酸 、 锌 作用下， 以 乙醚 、 水 为溶剂， 以33%的产率得到(S)-4-methyl-N-(1-phenyl-3-(phenylselanyl)propan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  亚硒酸锌在双相系统中未保护的氮丙啶的开环

  摘要：

  通过未保护的氮丙啶的开环反应制备了一组手性β-硒胺。在酸性条件下，二芳基或二烷基二硒化物被锌还原，并用未保护的氮丙啶处理，以高收率得到所需产物。也使用该方法获得了手性β-碲胺。

  DOI：

  10.1016/j.tetlet.2009.02.156

文献信息

• Mild and selective silicon-mediated access to enantioenriched 1,2-mercaptoamines and β-amino arylchalcogenides
  作者：Damiano Tanini、Cosimo Borgogni、Antonella Capperucci

  DOI：10.1039/c9nj00657e

  日期：——

  Metal-free ring opening reactions of activated and unactivated aziridines with different silyl chalcogenides are described. Judicious tuning of the reaction conditions enables the synthesis of chiral enantioenriched N-Ts and N-Boc 1,2-mercaptoamines in good yields from the corresponding aziridines and bis(trimethylsilyl)sulfide. N-Protected and N-H unactivated aziridines are efficiently converted into

  描述了活化的和未活化的氮丙啶与不同的甲硅烷基硫属元素化物的无金属开环反应。通过适当调节反应条件，可以从相应的氮丙啶和双（三甲基甲硅烷基）硫化物以高收率合成手性对映体富集的N -Ts和N -Boc 1,2-巯基胺。用合适的芳族硫属元素硅烷处理后，N-保护的和N -H未活化的氮丙啶被有效地转化为相应的β-芳族硫属元素胺。硅介导的开环反应以优异的区域选择性和立体特异性进行，从而可以使用各种各样的合成和生物学上有价值的对映体富集的硫属元素胺。
• One-Pot Synthesis of β-Amino/β-Hydroxy Selenides and Sulfides from Aziridines and Epoxides
  作者：Srinivasan Chandrasekaran、Venkataraman Ganesh

  DOI：10.1055/s-0029-1216960

  日期：2009.10

  Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a regio­selective manner. A simple, mild, cost-effective protocol has been developed to prepare β-amino and β-hydroxy sulfides and selenides in a one-pot operation.

  二芳基二硫和二硒化物在与隆伽利特（羟甲基亚磺酸钠）反应时容易发生裂解，生成相应的硫醇盐和硒醇盐物种，这些物质能够选择性地促进氮杂环和环氧化物的开环反应。已开发出一种简单、温和、成本效益高的一锅法操作，用于制备β-氨基和β-羟基硫化物和硒化物。
• Efficient Ring Opening of Protected and Unprotected Aziridines Promoted by Stable Zinc Selenolate in Ionic Liquid
  作者：Luciano Dornelles、Oscar Rodrigues、Antonio Braga、Syed Salman、Ricardo Schwab、Eduardo Alberto、Josimar Vargas

  DOI：10.1055/s-0030-1259082

  日期：2011.1

  A highly efficient protocol is reported for the synthesis of chiral β-seleno amines via the ring-opening reaction of aziridines. Under neutral conditions, employing a stable phenyl selenolate specie (PhSeZnBr) and (BMIM)BF4 as solvent, β-seleno amines were obtained in good to excellent yields. Reuse of the ionic liquid was also possible, and four runs were performed with no decrease in the yields.

  本研究报道了通过氮丙啶的开环反应合成手性δ-硒胺的高效方法。在中性条件下，采用稳定的苯基硒酸盐（PhSeZnBr）和 (BMIM)BF4 作为溶剂，δ-硒胺的产率从良好到极佳。离子液体也可以重复使用，在进行了四次运行后，产率没有下降。
• Ring opening of unprotected aziridines by zinc selenolates in a biphasic system
  作者：Antonio L. Braga、Ricardo S. Schwab、Eduardo E. Alberto、Syed M. Salman、Josimar Vargas、Juliano B. Azeredo

  DOI：10.1016/j.tetlet.2009.02.156

  日期：2009.5

  A set of chiral β-seleno amines were prepared by the ring-opening reaction of unprotected aziridines. Under acid conditions diaryl or dialkyl diselenides were reduced by zinc and treated with unprotected aziridines to produce the desired products in good yields. Chiral β-telluro amine was also obtained using this method.

  通过未保护的氮丙啶的开环反应制备了一组手性β-硒胺。在酸性条件下，二芳基或二烷基二硒化物被锌还原，并用未保护的氮丙啶处理，以高收率得到所需产物。也使用该方法获得了手性β-碲胺。
• 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.