(3S,6R)-1-[(tert-butoxy)carbonyl]-3-(2-methylpropene-3-yl)-6-[(S)-1-methylpropyl]-piperidin-2-one | 269066-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,6R)-1-[(tert-butoxy)carbonyl]-3-(2-methylpropene-3-yl)-6-[(S)-1-methylpropyl]-piperidin-2-one
• 英文别名: tert-butyl (3S,6R)-6-[(2S)-butan-2-yl]-3-(2-methylprop-2-enyl)-2-oxopiperidine-1-carboxylate
• CAS: 269066-54-8
• 化学式: C₁₈H₃₁NO₃
• 分子量: 309.449
• InChiKey: NSEJWBYYYCLAIC-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6R)-1-[(tert-butoxy)carbonyl]-3-(2-methylpropene-3-yl)-6-[(S)-1-methylpropyl]-piperidin-2-one 在 lithium peroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以91%的产率得到(2S,5R,6S)-5-{[(tert-butoxy)carbonyl]amino}-6-methyl-2-(2-methylpropene-3-yl)-octanoic acid
  参考文献：
  名称：

  Stereoselective Alkylation of N-Boc-protected-5-substituted δ-Lactams:  Synthesis of α,δ-Disubstituted δ-Amino Acids

  摘要：

  [GRAPHICS]N-Boc-protected-5-substituted delta-lactams were readily prepared from the corresponding beta(3)-amino acids. Alkylation reactions of their Na enolates with various electrophiles proceeded in high yields with high facial selectivity. The structure of the alkylation products was confirmed by Single-crystal X-ray analysis. This method provides a fast access to optically active alpha,delta-disubstituted delta-amino acids.

  DOI：

  10.1021/ol9913136
• 作为产物：
  描述：

  N-(t-butyloxycarbonyl)-β-homoisoleucine 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hexamethyldisilazane 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 (3S,6R)-1-[(tert-butoxy)carbonyl]-3-(2-methylpropene-3-yl)-6-[(S)-1-methylpropyl]-piperidin-2-one
  参考文献：
  名称：

  Stereoselective Alkylation of N-Boc-protected-5-substituted δ-Lactams:  Synthesis of α,δ-Disubstituted δ-Amino Acids

  摘要：

  [GRAPHICS]N-Boc-protected-5-substituted delta-lactams were readily prepared from the corresponding beta(3)-amino acids. Alkylation reactions of their Na enolates with various electrophiles proceeded in high yields with high facial selectivity. The structure of the alkylation products was confirmed by Single-crystal X-ray analysis. This method provides a fast access to optically active alpha,delta-disubstituted delta-amino acids.

  DOI：

  10.1021/ol9913136

文献信息

• Stereoselective Alkylation of <i>N</i>-Boc-protected-5-substituted δ-Lactams:  Synthesis of <i>α</i>,δ-Disubstituted δ-Amino Acids
  作者：J. Richard Casimir、Claude Didierjean、André Aubry、Marc Rodriguez、Jean-Paul Briand、Gilles Guichard

  DOI：10.1021/ol9913136

  日期：2000.4.1

  [GRAPHICS]N-Boc-protected-5-substituted delta-lactams were readily prepared from the corresponding beta(3)-amino acids. Alkylation reactions of their Na enolates with various electrophiles proceeded in high yields with high facial selectivity. The structure of the alkylation products was confirmed by Single-crystal X-ray analysis. This method provides a fast access to optically active alpha,delta-disubstituted delta-amino acids.