[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]boronic acid | 1160936-50-4

• 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: [3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]boronic acid
• CAS: 1160936-50-4
• 化学式: C₈H₇BCl₂F₂O₃
• 分子量: 270.856
• InChiKey: YJWWANIZFFYWSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-(5-bromo-3-fluoropyridin-2-yl)ethyl]acetamide 、 [3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]boronic acid 在 potassium phosphate 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 以96.6%的产率得到N-((1R)-1-{5-[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]-3-fluoropyridin-2-yl}ethyl)acetamide
  参考文献：
  名称：

  Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide

  摘要：

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.

  DOI：

  10.1021/jo802772d
• 作为产物：
  描述：

  1-bromo-3,5-dichloro-2-(2,2-difluoroethoxy)benzene 在 异丙基氯化镁 、 硼酸三异丙酯 、 盐酸 、 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到[3,5-dichloro-2-(2,2-difluoroethoxy)phenyl]boronic acid
  参考文献：
  名称：

  Practical Synthesis of a Potent Bradykinin B₁ Antagonist via Enantioselective Hydrogenation of a Pyridyl N-Acyl Enamide

  摘要：

  A practical and efficient synthesis of bradykinin B I antagonist I is described. A convergent strategy was utilized which involved synthesis of three fragments: 3, 6, and 7. Cross coupling of fragments 6 and 7 followed by amidation with 3 enabled efficient synthesis of I in 19 steps total, a 35% overall yield from commercially available pyridine 10. The key to the success of the synthesis was the development of a fluorodenitration step to install the fluorine in pyridine 7 and a catalytic enantioselective hydrogenation of N-acyl enamide 9 to set the stereochemistry.

  DOI：

  10.1021/jo802772d