(S)-N-3-methylbutylidene-4-methylbenzenesulfinamide | 161123-26-8

• 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)-N-3-methylbutylidene-4-methylbenzenesulfinamide
• 英文别名: (S)-4-methyl-N-(3-methylbutylidene)benzenesulfinamide
• CAS: 161123-26-8
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: GDNILMXYFGSGFP-HNNXBMFYSA-N

物化性质

• 沸点：
  355.8±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,3-二硫烷-2-甲酸乙酯 、 (S)-N-3-methylbutylidene-4-methylbenzenesulfinamide 在 lithium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到ethyl (S,S(S))-2-[1-(4-methylphenylsulfinylamino)-3-methylbutyl]-1,3-dithiolane-2-carboxylate
  参考文献：
  名称：

  Beyond the chiral pool: a general approach to β-amino-α-keto amides

  摘要：

  A simple route was developed for the synthesis of optically enriched beta-amino-alpha-keto amides. The highly diastereoselective addition of alkyl dithiolanecarboxylates to optically enriched sulfinimines affords the corresponding beta-amino-alpha-keto esters in which the ketone carbonyl group is protected as a dithiolane. Amidation of the ester functionality with a primary amine proceeds readily at room temperature. Treatment with HCl cleaves the N-S bond of the sulfinyl group to provide a free amine functionality, which can then be incorporated into a peptide. Removal of the dithiolane protecting group under oxidative conditions proceeds without epimerization as exemplified by a model dipeptide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.018

文献信息

• Synthesis of Enantiomerically Pure <i>anti</i>-1,2-Diaryl and <i>syn</i>-1,2-Alkylaryl <i>vic</i>-Selenoamines
  作者：José L. García Ruano、Esther Torrente、Inés Alonso、Mercedes Rodriguez、Ana M. Martín-Castro、Alessandro Degl’Innocenti、Lucrezia Frateschi、Antonella Capperucci

  DOI：10.1021/jo202611v

  日期：2012.2.17

  Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.
• Beyond the chiral pool: a general approach to β-amino-α-keto amides
  作者：Cristian L. Harrison、Mariusz Krawiec、Raymond E. Forslund、William A. Nugent

  DOI：10.1016/j.tet.2010.11.018

  日期：2011.1

  A simple route was developed for the synthesis of optically enriched beta-amino-alpha-keto amides. The highly diastereoselective addition of alkyl dithiolanecarboxylates to optically enriched sulfinimines affords the corresponding beta-amino-alpha-keto esters in which the ketone carbonyl group is protected as a dithiolane. Amidation of the ester functionality with a primary amine proceeds readily at room temperature. Treatment with HCl cleaves the N-S bond of the sulfinyl group to provide a free amine functionality, which can then be incorporated into a peptide. Removal of the dithiolane protecting group under oxidative conditions proceeds without epimerization as exemplified by a model dipeptide. (C) 2010 Elsevier Ltd. All rights reserved.