3-chloro-5-[2-chloro-5-(7-oxy-1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile | 1173989-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-5-[2-chloro-5-(7-oxy-1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile
• CAS: 1173989-69-9
• 化学式: C₂₀H₁₂Cl₂N₄O₃
• 分子量: 427.246
• InChiKey: FSPDIPJNLGYNNA-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C
• 沸点：
  631.1±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  97.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡喃 、 3-chloro-5-[2-chloro-5-(7-oxy-1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以80%的产率得到3-chloro-5-{2-chloro-5-[7-oxy-1-(tetrahydropyran-2yl)-1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy]phenoxy}benzonitrile
  参考文献：
  名称：

  Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors

  摘要：

  The development of practical and efficient syntheses of the potent non-nucleoside reverse transcriptase inhibitors I and 2 is described. The preparation of I proceeded in four synthetic steps and in 48% overall yield from 3. The long-term synthesis of 2 proceeded in nine synthetic steps and in 47% overall yield from commercially available 2,6-diflurorpyridine. The route to 2 was highlighted by the three-step synthesis of intermediate 22 and the high yielding coupling between 18 and phenol 8. The overall sequence required no chromatography and has successfully been utilized for the manufacture of 2 on large scale. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.03.084
• 作为产物：
  描述：

  3-chloro-5-[2-chloro-5-(1H-pyrazolo[3,4-b]pyridine-3-yl-methoxy)phenoxy]benzonitrile 在 间氯过氧苯甲酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以97.9%的产率得到3-chloro-5-[2-chloro-5-(7-oxy-1H-pyrazolo[3,4-b]pyridin-3-ylmethoxy)phenoxy]benzonitrile
  参考文献：
  名称：

  Development of a Safe and Practical N-Oxidation Procedure Using m-CPBA in Acetic Acid

  摘要：

  A safe and practical procedure for the N-oxidation of pyrazolopyridine 4 using meta-chloroperbenzoic acid (m-CPBA) in acetic acid is described. Key safety experiments are outlined which have led to the development and implementation of this reaction on 28-kg scale in 98% isolated yield.

  DOI：

  10.1021/op100280c