(S)-4-methyl-N-(3-methyl-1-(phenylselanyl)butan-2-yl)benzenesulfonamide | 1034566-21-6

• 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-(phenylselanyl)butan-2-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(2S)-3-methyl-1-phenylselanylbutan-2-yl]benzenesulfonamide
• CAS: 1034566-21-6
• 化学式: C₁₈H₂₃NO₂SSe
• 分子量: 396.412
• InChiKey: MFBHUQKNENLZMT-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 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：
  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 、 (2S)-2-isopropyl-1-[(4-methylphenyl)sulfonyl]aziridine 在 盐酸 、 锌 作用下， 以 水 为溶剂， 反应 1.5h， 以85%的产率得到(S)-4-methyl-N-(3-methyl-1-(phenylselanyl)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

• Modular Synthesis of Chiral N-Protected β-Seleno Amines and Amides via Cleavage of 2-Oxazolidinones and Application in Palladium-Catalyzed Asymmetric­ Allylic Alkylation
  作者：Antonio Braga、Jasquer Sehnem、Fabrício Vargas、Priscila Milani、Vanessa Nascimento

  DOI：10.1055/s-2008-1042938

  日期：2008.4

  A set of chiral β-seleno amines have been efficiently synthesized via the ring-opening reaction of chiral N-acyl oxazolidin-ones by selenium nucleophiles. These compounds could be transformed into β-seleno amides by reaction with acid chlorides. The present method is applicable to the synthesis of β-chalcogeno amides containing selenium, sulfur and tellurium atoms in good yields. Additionally, these

  硒亲核试剂通过手性N-酰基恶唑烷酮的开环反应有效合成了一组手性β-硒胺。这些化合物可以通过与酰氯反应转化为β-硒代酰胺。本方法适用于以良好收率合成含硒、硫和碲原子的β-硫族酰胺。此外，这些新化合物在钯催化的不对称烯丙基烷基化反应中作为配体进行了评估，得到了高达 98% ee 的相应烷基化产物。
• 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。