(2S,(S)S)-N-(p-tolylsulfinyl)-1-nitro-3-methylbutan-2-amine | 868056-43-3

• 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: (2S,(S)S)-N-(p-tolylsulfinyl)-1-nitro-3-methylbutan-2-amine
• 英文别名: (S)-4-methyl-N-[(2S)-3-methyl-1-nitrobutan-2-yl]benzenesulfinamide
• CAS: 868056-43-3
• 化学式: C₁₂H₁₈N₂O₃S
• 分子量: 270.353
• InChiKey: BBCLGDKFNXSYHR-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,(S)S)-N-(p-tolylsulfinyl)-1-nitro-3-methylbutan-2-amine 、 methyl 4,4,4-trifluorocrotonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 methyl 6-methyl-5-N-(p-tolylsulfinyl)amino-4-nitro-3-trifluoromethyl-heptanate
  参考文献：
  名称：

  An Efficient Method for the Synthesis of Nitropiperidones

  摘要：

  [GRAPHICS]A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha, beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.

  DOI：

  10.1021/jo702130a
• 作为产物：
  描述：

  硝基甲烷 、 (S)-N-(2-methylpropylidene)-p-toluenesulfinamide 在 sodium hydroxide 作用下， 生成 (2S,(S)S)-N-(p-tolylsulfinyl)-1-nitro-3-methylbutan-2-amine
  参考文献：
  名称：

  An Efficient Method for the Synthesis of Nitropiperidones

  摘要：

  [GRAPHICS]A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha, beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.

  DOI：

  10.1021/jo702130a

文献信息

• Asymmetric Aza-Henry Reactions from <i>N</i>-<i>p</i>-Tolylsulfinylimines
  作者：José Luis García Ruano、Markus Topp、Jesús López-Cantarero、José Alemán、Modesto J. Remuiñán、M. Belén Cid

  DOI：10.1021/ol051580d

  日期：2005.9.1

  [reaction: see text] N-Sulfinylimines derived from aromatic or aliphatic aldehydes and ketones react with nitromethane and NaOH in a highly diastereoselective manner under mild conditions. In the presence of TBAF, the reaction rates are strongly increased and the stereoselectivity is inverted. This method provides enantiomerically pure beta-nitroamines derived from enolizable aldimines and ketimines

  [反应：见正文]在温和条件下，衍生自芳族或脂族醛和酮的N-亚磺酰亚胺与硝基甲烷和NaOH以高度非对映选择性的方式反应。在TBAF的存在下，反应速率大大提高并且立体选择性反转。该方法提供了对映体纯的β-硝基胺，其衍生自可烯醇化的亚胺和酮亚胺，到目前为止，氮杂-亨利反应很难获得。