(+)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(2-phenylethyl)-4-(p-tolylsulfinyl)piperazin-2-one | 878556-94-6

• 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: (+)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(2-phenylethyl)-4-(p-tolylsulfinyl)piperazin-2-one
• 英文别名: (5R,6S)-1-benzyl-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[(S)-(4-methylphenyl)sulfinyl]-5-(2-phenylethyl)piperazin-2-one
• CAS: 878556-94-6
• 化学式: C₃₃H₄₄N₂O₃SSi
• 分子量: 576.875
• InChiKey: OYZOFCZYEHLKFO-CKIFNATCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(2-phenylethyl)-4-(p-tolylsulfinyl)piperazin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(2-phenylethyl)-5,6-dihydro-1H-pyrazin-2-one
  参考文献：
  名称：

  Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal N-Sulfinyl Diamines

  摘要：

  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.

  DOI：

  10.1021/jo052077h
• 作为产物：
  描述：

  (+)-N-benzyl-N-[(1S,2R,S_S)-1-(t-butyldimethylsilyloxymethyl)-4-phenyl-2-(p-tolylsulfinylamino)but-1-yl]-2-chloroacetamide 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以86%的产率得到(+)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(2-phenylethyl)-4-(p-tolylsulfinyl)piperazin-2-one
  参考文献：
  名称：

  Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal N-Sulfinyl Diamines

  摘要：

  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.

  DOI：

  10.1021/jo052077h

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.