2-{4-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazin-1-yl}-pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-{4-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazin-1-yl}-pyrimidine
• 英文别名: 2-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazin-1-yl)pyrimidine；2-[4-[[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazin-1-yl]pyrimidine
• 化学式: C₂₁H₂₉BN₄O₂
• 分子量: 380.298
• InChiKey: HWHSGXWBWYKJGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-溴-4-硝基苯 、 2-{4-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazin-1-yl}-pyrimidine 在 四丁基溴化铵 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.17h， 以56%的产率得到2-(4-((4'-nitrobiphenyl-4-yl)methyl)piperazin-1-yl)pyrimidine
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g
• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 2-溴乙基基苯硼酸频哪醇酯 在 PS-NMM 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以100%的产率得到2-{4-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperazin-1-yl}-pyrimidine
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g

文献信息

• Synthesis of ortho-modified mercapto- and piperazino-methyl-phenylboronic acid derivatives
  作者：John Spencer、Andrew P. Burd、Christopher A. Goodwin、Sandrine A.M. Mérette、Michael F. Scully、Trushar Adatia、John J. Deadman

  DOI：10.1016/s0040-4020(01)01028-6

  日期：2002.2

  The synthesis of 2-mercapto- and 2-piperazino- (methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolanes 4 and 5, respectively, is described and their inhibitory activity against serine proteases including thrombin was measured. Some of these compounds were studied in both the solid state and in solution, displaying no S-B coordination and only weak N-B coordination. (C) 2002 Elsevier Science Ltd. All rights reserved.