2-[(E)-2-bromovinyl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione | 1005452-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(E)-2-bromovinyl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• 英文别名: (E)-(2-bromovinyl)boronic acid MIDA ester；trans-1-bromovinylboronic acid MIDA ester；2-[(E)-2-bromoethenyl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• CAS: 1005452-52-7
• 化学式: C₇H₉BBrNO₄
• 分子量: 261.868
• InChiKey: ALXOFLXCBIRRRC-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-bromovinyl]-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 、 4-甲硫基苯硼酸 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以87%的产率得到(E)-(4-(methylthio)styryl)boronic acid
  参考文献：
  名称：

  One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis

  摘要：

  Formal homologation of sp(2)-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

  DOI：

  10.1021/acs.orglett.5b03030

文献信息

• [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：VERTEX PHARMA

  公开号：WO2014100158A1

  公开（公告）日：2014-06-26

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物具有化学式（I）。该发明还提供含有这些化合物的药学上可接受的组合物，以及使用这些组合物治疗细菌感染的方法。最后，该发明提供了制备本发明化合物的方法。
• Nickel-Catalyzed Enantioselective Cross-Coupling of <i>N</i>-Hydroxyphthalimide Esters with Vinyl Bromides
  作者：Naoyuki Suzuki、Julie L. Hofstra、Kelsey E. Poremba、Sarah E. Reisman

  DOI：10.1021/acs.orglett.7b00793

  日期：2017.4.21

  An enantioselective Ni-catalyzed cross-coupling of NT-hyciroxyphthalimide esters with Vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetralds(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.
• One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis
  作者：Calum W. Muir、Julien C. Vantourout、Albert Isidro-Llobet、Simon J. F. Macdonald、Allan J. B. Watson

  DOI：10.1021/acs.orglett.5b03030

  日期：2015.12.18

  Formal homologation of sp(2)-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.