6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde | 920744-20-3

• 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: 6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde
• 英文别名: 6-chloro-4-hydroxy-2-oxo-5-phenyl-1H-pyridine-3-carbaldehyde
• CAS: 920744-20-3
• 化学式: C₁₂H₈ClNO₃
• 分子量: 249.653
• InChiKey: UMJMTCDEZSQUOW-UHFFFAOYSA-N

物化性质

• 沸点：
  370.9±42.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde 在 potassium carbonate 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 (2S,3R)-3-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-3-hydroxy-2-methylpropanal
  参考文献：
  名称：

  Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure

  摘要：

  Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.025
• 作为产物：
  描述：

  苯乙腈 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 116.0h， 生成 6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde
  参考文献：
  名称：

  Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure

  摘要：

  Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.025

文献信息

• New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs
  作者：Nicolas Brondel、Brigitte Renoux、Jean-Pierre Gesson

  DOI：10.1016/j.tetlet.2006.10.102

  日期：2006.12

  An efficient method for the synthesis of antitumor TMC-69-6H and related analogs which have been demonstrated to be phosphatase (PTP1B, VHR, and PP1) inhibitors, is reported. This strategy involves two key steps: a diastereoselective aldol reaction and a one-pot tandem ring-closing and cross metathesis for the construction of the pyran moiety. (c) 2006 Elsevier Ltd. All rights reserved.