2-[(4-Methoxyphenyl)methyl]-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phthalazin-1-one | 1318877-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[(4-Methoxyphenyl)methyl]-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phthalazin-1-one
• CAS: 1318877-19-8
• 化学式: C₂₈H₂₉BN₂O₄
• 分子量: 468.36
• InChiKey: BGEYIJMCQYPPCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-Bromophenyl)-2-[(4-methoxyphenyl)methyl]phthalazin-1-one 、 联硼酸频那醇酯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以65%的产率得到2-[(4-Methoxyphenyl)methyl]-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phthalazin-1-one
  参考文献：
  名称：

  Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents

  摘要：

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.032