N-<(R)-(methoxycarbonyl)benzyl>-(6S)-2,3-didehydro-6-phenylpiperidin-4-one | 142764-49-6

• 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: N-<(R)-(methoxycarbonyl)benzyl>-(6S)-2,3-didehydro-6-phenylpiperidin-4-one
• 英文别名: methyl (2S)-2-[(2R)-4-oxo-2-phenyl-2,3-dihydropyridin-1-yl]-2-phenylacetate
• CAS: 142764-49-6
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: VXBUPCFBNSPKPS-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (benzylidene-amino)-phenyl-acetic acid methyl ester 在 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-<(R)-(methoxycarbonyl)benzyl>-(6S)-2,3-didehydro-6-phenylpiperidin-4-one 、 N-<(R)-(methoxycarbonyl)benzyl>-(6R)-2,3-didehydro-6-phenylpiperidin-4-one
  参考文献：
  名称：

  Asymmetric tandem Mannich-Michael reactions of amino acid ester imines with Danishefsky's diene

  摘要：

  Imines 1 derived from aromatic, aliphatic, and functionalized aldehydes and various amino acid esters react with Danishefsky's diene under Lewis acid catalysis via a tandem Mannich-Michael mechanism to give cyclic 6-substituted 2,3-didehydro-4-piperidinones in good to high yields and with diastereomeric ratios reaching from 92:8 up to 97:3. The chiral auxiliary is removed by conversion of the alpha-C atom of the amino acid into an acetalic center, employing a Curtius reaction as the key step. For the elucidation of the absolute configuration, the alkaloids (S)-coniine and (R)-delta-coniceine are synthesized from the enaminones 5i and 5r.

  DOI：

  10.1021/jo00042a027

文献信息

• Asymmetric tandem Mannich-Michael reactions of amino acid ester imines with Danishefsky's diene
  作者：H. Waldmann、M. Braun

  DOI：10.1021/jo00042a027

  日期：1992.7

  Imines 1 derived from aromatic, aliphatic, and functionalized aldehydes and various amino acid esters react with Danishefsky's diene under Lewis acid catalysis via a tandem Mannich-Michael mechanism to give cyclic 6-substituted 2,3-didehydro-4-piperidinones in good to high yields and with diastereomeric ratios reaching from 92:8 up to 97:3. The chiral auxiliary is removed by conversion of the alpha-C atom of the amino acid into an acetalic center, employing a Curtius reaction as the key step. For the elucidation of the absolute configuration, the alkaloids (S)-coniine and (R)-delta-coniceine are synthesized from the enaminones 5i and 5r.