2,4-bis(benzyloxy)-6-chloro-5-phenylpyridine-3-carbaldehyde | 920744-21-4

• 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: 2,4-bis(benzyloxy)-6-chloro-5-phenylpyridine-3-carbaldehyde
• 英文别名: 6-chloro-5-phenyl-2,4-bis(phenylmethoxy)pyridine-3-carbaldehyde
• CAS: 920744-21-4
• 化学式: C₂₆H₂₀ClNO₃
• 分子量: 429.903
• InChiKey: YYVPCVFCWGUOQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  581.8±50.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis(benzyloxy)-6-chloro-5-phenylpyridine-3-carbaldehyde 在 L-脯氨酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 73.0h， 生成 (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol
  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 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.0h， 生成 2,4-bis(benzyloxy)-6-chloro-5-phenylpyridine-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.
• Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure
  作者：Sophie Vuong、Nicolas Brondel、Christophe Len、Sébastien Papot、Brigitte Renoux

  DOI：10.1016/j.tet.2011.11.025

  日期：2012.1

  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.