1-benzyl-5-[hydroxy(phenyl)methyl]-6-methyl-1,2,3,4-tetrahydro-2-pyridinone | 202188-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-benzyl-5-[hydroxy(phenyl)methyl]-6-methyl-1,2,3,4-tetrahydro-2-pyridinone
• 英文别名: 1-benzyl-5-[hydroxy(phenyl)methyl]-6-methyl-3,4-dihydropyridin-2-one
• CAS: 202188-63-4
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: QAYNYSNAAQMBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-[hydroxy(phenyl)methyl]-6-methyl-1,2,3,4-tetrahydro-2-pyridinone 以 溶剂黄146 为溶剂， 反应 1.0h， 以85%的产率得到6-benzylamino-6-methyl-5-[(E)-1-phenylmethylidene]-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：

  (2Z)-3-(benzylamino)-1-phenylbut-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-benzyl-5-[hydroxy(phenyl)methyl]-6-methyl-1,2,3,4-tetrahydro-2-pyridinone
  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

文献信息

• 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
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1016/s0040-4020(97)10333-7

  日期：1998.1

  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.