(+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(1-naphthyl)-5,6-dihydro-1H-pyrazin-2-one | 878557-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(1-naphthyl)-5,6-dihydro-1H-pyrazin-2-one
• 英文别名: (2R,3S)-4-benzyl-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-naphthalen-1-yl-2,3-dihydropyrazin-5-one
• CAS: 878557-00-7
• 化学式: C₂₈H₃₄N₂O₂Si
• 分子量: 458.676
• InChiKey: CEGSMNPUQNNFKE-XNMGPUDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(1-naphthyl)-5,6-dihydro-1H-pyrazin-2-one 在 三甲基氯硅烷 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 生成 methyl (2S)-2-[(2R,5S,6R)-4-benzyl-5-(hydroxymethyl)-6-naphthalen-1-yl-3-oxopiperazin-2-yl]-2-(2,5-dimethoxyphenyl)acetate
  参考文献：
  名称：

  对5,6-二氢吡嗪-2-（1 H）-one的高度非对映选择性施陶丁格反应。对映体稠合的氧代哌嗪子-β-内酰胺类化合物的合成

  摘要：

  已经通过官能化的烯酮与5，6-二氢吡嗪-2（1 H）-ones 1之间的斯托丁格反应（Staudinger reaction ）进行了非对映选择性合成稠合的氧代哌嗪子-β-内酰胺2。β-内酰胺环的进一步裂解产生没有差向异构且产率高的2-氧代哌嗪-3-乙酸衍生物7。

  DOI：

  10.1016/j.tetlet.2006.10.044
• 作为产物：
  描述：

  (-)-(5R,6S,S_S)-1-benzyl-6-[(t-butyldimethylsilyloxy)methyl]-5-(1-naphthyl)-4-(p-tolylsulfinyl)piperazin-2-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到(+)-(5R,6S)-1-benzyl-6-(t-butyldimethylsilyloxymethyl)-5-(1-naphthyl)-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

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.
• Highly diastereoselective Staudinger reaction on 5,6-dihydropyrazin-2-(1H)-ones. Synthesis of enantiopure fused oxopiperazino-β-lactams
  作者：Alma Viso、Roberto Fernández de la Pradilla、Aida Flores

  DOI：10.1016/j.tetlet.2006.10.044

  日期：2006.12

  The highly diastereoselective synthesis of fused oxopiperazino-β-lactams 2 by Staudinger reaction between functionalized ketenes and 5,6-dihydropyrazin-2(1H)-ones 1 has been carried out. Further cleavage of the β-lactam ring produced 2-oxopiperazine-3-acetic acid derivatives 7 with no epimerization and in good yields.

  已经通过官能化的烯酮与5，6-二氢吡嗪-2（1 H）-ones 1之间的斯托丁格反应（Staudinger reaction ）进行了非对映选择性合成稠合的氧代哌嗪子-β-内酰胺2。β-内酰胺环的进一步裂解产生没有差向异构且产率高的2-氧代哌嗪-3-乙酸衍生物7。
• 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.