2-(tert-butoxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine | 1448788-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(tert-butoxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine
• 英文别名: 6-Tert-butoxypyrazine-2-boronic acid pinacol ester；2-[(2-methylpropan-2-yl)oxy]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine
• CAS: 1448788-59-7
• 化学式: C₁₄H₂₃BN₂O₃
• 分子量: 278.159
• InChiKey: LYGNCCVBZFPSRF-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Bromo-3-(4-methylsulfonylphenoxy)-5-propan-2-yloxybenzene 、 2-(tert-butoxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到2-[(2-Methylpropan-2-yl)oxy]-6-[3-(4-methylsulfonylphenoxy)-5-propan-2-yloxyphenyl]pyrazine
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036
• 作为产物：
  描述：

  2-tert-butoxy-6-chloro-pyrazine 、 联硼酸频那醇酯 在 potassium acetate 、 palladium diacetate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以18 g的产率得到2-(tert-butoxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine
  参考文献：
  名称：

  通过钯催化的宫浦硼化反应高效合成吡嗪硼酸酯

  摘要：

  已经开发了一种简便有效的方案，用于钯与B 2 pin 2的氯吡嗪的Miyaura硼酸酯化反应。从相应的氯吡嗪以中等到良好的产率可以容易地制备一定范围的难以获得的吡嗪硼酸酯。

  DOI：

  10.1016/j.tetlet.2017.01.043

文献信息

• Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif
  作者：Kevin J. Filipski、Angel Guzman-Perez、Jianwei Bian、Christian Perreault、Gary E. Aspnes、Mary T. Didiuk、Robert L. Dow、Richard F. Hank、Christopher S. Jones、Robert J. Maguire、Meihua Tu、Dongxiang Zeng、Shenping Liu、John D. Knafels、John Litchfield、Karen Atkinson、David R. Derksen、Francis Bourbonais、Ketan S. Gajiwala、Michael Hickey、Theodore O. Johnson、Paul S. Humphries、Jeffrey A. Pfefferkorn

  DOI：10.1016/j.bmcl.2013.06.036

  日期：2013.8

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient synthesis of pyrazine boronic esters via palladium-catalyzed Miyaura borylation
  作者：Hongtao Lu、Shengqiang Wang、Jingya Li、Dapeng Zou、Yusheng Wu、Yangjie Wu

  DOI：10.1016/j.tetlet.2017.01.043

  日期：2017.3

  A facile and efficient protocol for palladium-catalyzed Miyaura borylation reaction of chloropyrazines with B2pin2 has been developed. A certain range of difficult-to-access pyrazine boronic esters can be easily prepared from the corresponding chloropyrazines in moderate to good yields.

  已经开发了一种简便有效的方案，用于钯与B 2 pin 2的氯吡嗪的Miyaura硼酸酯化反应。从相应的氯吡嗪以中等到良好的产率可以容易地制备一定范围的难以获得的吡嗪硼酸酯。