(+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(i-propyl)prop-1-yl]-p-tolylsulfinamide | 878556-88-8

• 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: (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(i-propyl)prop-1-yl]-p-tolylsulfinamide
• 英文别名: (S)-N-[(2S,3R)-2-(benzylamino)-1-[tert-butyl(dimethyl)silyl]oxy-4-methylpentan-3-yl]-4-methylbenzenesulfinamide
• CAS: 878556-88-8
• 化学式: C₂₆H₄₂N₂O₂SSi
• 分子量: 474.783
• InChiKey: RVULDUXDHVDTAQ-UOMUQXIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(i-propyl)prop-1-yl]-p-tolylsulfinamide 在 sodium hydride 、 碳酸氢钠 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(i-propyl)-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：

  叔丁基二甲基氯硅烷 、 (+)-(2S,3R,S_S)-2-(benzylamino)-4-methyl-3-(p-tolylsulfinylamino)pentan-1-ol 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(+)-(1R,2S,S_S)-N-[2-benzylamino-3-(t-butyldimethylsilyloxy)-1-(i-propyl)prop-1-yl]-p-tolylsulfinamide
  参考文献：
  名称：

  手性亚磺酰胺基磺酰胺的合成及其作为醛对映选择性乙基化的配体的评价

  摘要：

  从亚磺胺合成了手性亚磺酰胺基-磺酰胺配体家族，并已被评估为将二乙基锌与Ti（O i Pr）4对映选择性加成到醛中的配体。这些二氨基化合物的结构已被系统地修改以优化结果。

  DOI：

  10.1016/j.tet.2009.02.033

文献信息

• Highly diastereoselective Barbier allylation and iminium cyclization: a simple entry to bicyclic and tricyclic piperazinones
  作者：A. Viso、R. Fernández de la Pradilla、A. Flores、M.A. del Águila

  DOI：10.1016/j.tet.2008.10.034

  日期：2008.12

  Barbier allylation of 5,6-dihydropyrazin-2(1H)-ones leads to a single isomer of 3 -alylpiperazin-2-ones in high yields. Further Pictet-Spengler-Grieco cyclization of 3-allylpiperazin-2-ones with aldehydes provides bicyclic and tricyclic piperazinones with high diastereoselectivity. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of chiral sulfinamido-sulfonamides and their evaluation as ligands for the enantioselective ethylation of aldehydes
  作者：Alma Viso、Roberto Fernández de la Pradilla、Mercedes Ureña

  DOI：10.1016/j.tet.2009.02.033

  日期：2009.5

  A family of chiral sulfinamido-sulfonamide ligands have been synthesized from sulfinimines and has been evaluated as ligands for the enantioselective addition of diethylzinc to aldehydes with Ti(OiPr)4. The structure of these diamino compounds has been systematically modified to optimize the results.

  从亚磺胺合成了手性亚磺酰胺基-磺酰胺配体家族，并已被评估为将二乙基锌与Ti（O i Pr）4对映选择性加成到醛中的配体。这些二氨基化合物的结构已被系统地修改以优化结果。
• 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.