(6S)-6-<2-(ethoxycarbonyl)ethyl>-2,3-didehydropiperidin-4-one | 132599-88-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (6S)-6-<2-(ethoxycarbonyl)ethyl>-2,3-didehydropiperidin-4-one
• 英文别名: (6S)-6-[2-(ethoxycarbonyl)ethyl]-2,3-didehydropiperidin-4-one；ethyl 3-[(2S)-4-oxo-2,3-dihydro-1H-pyridin-2-yl]propanoate
• CAS: 132599-88-3
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: TWJYLSUNSOENGE-QMMMGPOBSA-N

物化性质

• 沸点：
  309.6±31.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (6S)-6-<2-(ethoxycarbonyl)ethyl>-2,3-didehydropiperidin-4-one 在 4 A molecular sieve 、 三氟化硼乙醚 、 L-Selectride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.75h， 生成 (6S)-4-(1,3-dithiolan-4-yl)indolizidin-9-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
• 作为产物：
  描述：

  (S)-2-[3-Ethoxycarbonyl-prop-(E)-ylideneamino]-3-methyl-butyric acid benzyl ester 在 palladium on activated charcoal 、 二氯乙基铝 叠氮磷酸二苯酯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 (6S)-6-<2-(ethoxycarbonyl)ethyl>-2,3-didehydropiperidin-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

• Waldmann, Herbert; Braun, Matthias; Draeger, Martin, Angewandte Chemie, 1990, vol. 102, # 12, p. 1445 - 1447
  作者：Waldmann, Herbert、Braun, Matthias、Draeger, Martin

  DOI：——

  日期：——