(6S)-5-[(E)-ethylidene]-6-methyl-6-{[(1R)-1-phenylethyl]amino}-tetrahydro-2H-2-pyranone | 202188-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (6S)-5-[(E)-ethylidene]-6-methyl-6-{[(1R)-1-phenylethyl]amino}-tetrahydro-2H-2-pyranone
• 英文别名: (5E,6S)-5-ethylidene-6-methyl-6-[[(1R)-1-phenylethyl]amino]oxan-2-one
• CAS: 202188-76-9
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: OSKBFKYPNXQUSS-LKIUWRSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6S)-5-[(E)-ethylidene]-6-methyl-6-{[(1R)-1-phenylethyl]amino}-tetrahydro-2H-2-pyranone 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 15.0h， 以93%的产率得到5-ethyl-6-methyl-6-{[(1R)-1-phenylethyl]amino}tetrahydro-2H-2-pyranone
  参考文献：
  名称：

  Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

  摘要：

  A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10333-7
• 作为产物：
  描述：

  5-(1-hydroxyethyl)-6-methyl-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydro-2-pyridinone 以 溶剂黄146 为溶剂， 反应 1.0h， 以72%的产率得到(6S)-5-[(E)-ethylidene]-6-methyl-6-{[(1R)-1-phenylethyl]amino}-tetrahydro-2H-2-pyranone
  参考文献：
  名称：

  Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

  摘要：

  A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10333-7