(+)-methyl [(2S,3R,Ss)-2-amino-3-(p-tolylsulfinylamino)]butanoate | 675124-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-methyl [(2S,3R,Ss)-2-amino-3-(p-tolylsulfinylamino)]butanoate
• CAS: 675124-87-5
• 化学式: C₁₂H₁₈N₂O₃S
• 分子量: 270.353
• InChiKey: HKVRURJDHUDSKP-TUFKUPSJSA-N

物化性质

• 沸点：
  427.1±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (+)-methyl [(2S,3R,Ss)-2-amino-3-(p-tolylsulfinylamino)]butanoate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以65%的产率得到(+)-methyl [(2S,3R,Ss)-2-di(benzyl)amino-3-(p-tolylsulfinylamino)]butanoate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j
• 作为产物：
  描述：

  (+)-methyl [(2S,4S,5R,S_S)-5-methyl-2-phenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate 在 磷酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以81%的产率得到(+)-methyl [(2S,3R,Ss)-2-amino-3-(p-tolylsulfinylamino)]butanoate
  参考文献：
  名称：

  Fine-Tuned Aminal Cleavage:  A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

  摘要：

  A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H3PO4 in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.

  DOI：

  10.1021/jo035613j

文献信息

• Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal <i>N</i>-Sulfinyl Diamines
  作者：Alma Viso、Roberto Fernández de la Pradilla、Aida Flores、Ana García、Mariola Tortosa、María L. López-Rodríguez

  DOI：10.1021/jo052077h

  日期：2006.2.1

  Enantiopure 1-benzyl-2,3-disubstituted piperazines (4) have been synthesized by treatment of N-sulfinyl-N-benzyldiamino alcohols (1) with diethyl oxalate and sodium methoxide followed by reduction with borane. Alternatively, the sulfinamido group was preserved by an N-acylation/cyclization protocol using alpha-chloroacetyl chloride that led to the synthesis of N-sulfinyl ketopiperazines (11). Ensuing elimination of the suffinyl group with NaH produced imino ketopiperazines (9) that are suitably functionalized for nucleophilic addition to the imino moiety. Stereoselective and high yielding allylation of imino ketopiperazines (9c) was achieved under Barbier conditions using CeCl3 center dot 7H(2)O as the additive.