2-(5-chloro-2-{[4-chloro-2-fluorophenylmethyl]oxy}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 892664-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-chloro-2-{[4-chloro-2-fluorophenylmethyl]oxy}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-{5-Chloro-2-[(4-chloro-2-fluorophenyl)methoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[5-chloro-2-[(4-chloro-2-fluorophenyl)methoxy]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 892664-20-9
• 化学式: C₁₉H₂₀BCl₂FO₃
• 分子量: 397.081
• InChiKey: SGWVAKOLWOYKSN-UHFFFAOYSA-N

物化性质

• 沸点：
  484.2±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-chloro-2-{[4-chloro-2-fluorophenylmethyl]oxy}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 potassium carbonate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 6-[[5-氯-2-[(4-氯-2-氟苯基)甲氧基]苯基]甲基]吡啶-2-羧酸
  参考文献：
  名称：

  Selection and Development of the Manufacturing Route for EP₁ Antagonist GSK269984B

  摘要：

  A potential manufacturing route for the EP1 antagonist GSK269984B was developed. Four synthetic approaches were examined, and a successful realisation of each is presented. The rationale supporting selection of the preferred route is discussed. This route utilised a phenolic aldol reaction as the key step and relied on selective hydrogenolysis to reduce an intermediate diarylmethanol. Further optimisation of the selected route is presented, delivering GSK269984B in three stages and 46% overall yield from readily available starting materials.

  DOI：

  10.1021/op100072y
• 作为产物：
  描述：

  4-氯-2-碘苯甲醚, 在 异丙基氯化镁 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 2-(5-chloro-2-{[4-chloro-2-fluorophenylmethyl]oxy}phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Selection and Development of the Manufacturing Route for EP₁ Antagonist GSK269984B

  摘要：

  A potential manufacturing route for the EP1 antagonist GSK269984B was developed. Four synthetic approaches were examined, and a successful realisation of each is presented. The rationale supporting selection of the preferred route is discussed. This route utilised a phenolic aldol reaction as the key step and relied on selective hydrogenolysis to reduce an intermediate diarylmethanol. Further optimisation of the selected route is presented, delivering GSK269984B in three stages and 46% overall yield from readily available starting materials.

  DOI：

  10.1021/op100072y

文献信息

• Mild and Selective Synthesis of an Aryl Boronic Ester by Equilibration of Mixtures of Boronic and Borinic Acid Derivatives
  作者：Vanessa F. Hawkins、Mark C. Wilkinson、Matthew Whiting

  DOI：10.1021/op800169s

  日期：2008.11.21

  of aryl Grignard reagents with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (isopropyl pinacol borate) under noncryogenic conditions can lead to mixtures of the corresponding boronic ester along with, generally undesired, borinic acid derivatives. We have found that in certain cases gentle heating of the crude reaction mixtures leads to complete equilibration to give the borinic esters as the

  在非低温条件下用2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷（异丙基频哪醇硼酸酯）淬灭芳基格氏试剂会导致相应的硼酸酯与通常不希望的硼酸酯混合物，硼酸衍生物。我们发现，在某些情况下，粗制反应混合物的温和加热导致完全平衡，从而得到硼酸酯作为唯一产物，然后可以高收率分离。这种新的平衡可以减少使用低温条件或大量过量的试剂在硼酸酯合成过程中获得选择性的需要。
• WO2007/128752
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• WO2006/66968
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