2-pyrone-5-boronate | 400089-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-pyrone-5-boronate
• 英文别名: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran-2-one；2H-Pyran-2-one, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-；5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyran-2-one
• CAS: 400089-54-5
• 化学式: C₁₁H₁₅BO₄
• 分子量: 222.049
• InChiKey: TXWQDSGRWRSQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-pyrone-5-boronate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 Rh/Al₂O₃ potassium phosphate 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  A New Route to 5-Aryl and 5-Heteroaryl-2-pyrones via Suzuki Coupling of a 2-Pyrone-5-boronate ester

  摘要：

  本文介绍了 2-吡喃酮-5-硼酸酯 5 的合成及其与一系列芳基和杂芳基卤化物和三酸盐的钯催化偶联反应。

  DOI：

  10.1055/s-2003-36789
• 作为产物：
  描述：

  2H-吡喃-2-酮 在 bis-triphenylphosphine-palladium(II) chloride 溴 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 2-pyrone-5-boronate
  参考文献：
  名称：

  A Suzuki coupling approach to bufadienolides

  摘要：

  A high yielding route to bufadienolide type steroids using a novel Suzuki Coupling reaction between a range of steroid vinyl triflates and 2-pyrone-5-boronate 11 is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01980-3

文献信息

• [EN] COMPOUNDS USEFUL AS INHIBITORS OF ATR KINASE<br/>[FR] COMPOSÉS UTILES COMME INHIBITEURS DE LA KINASE ATR
  申请人：VERTEX PHARMA

  公开号：WO2011143426A1

  公开（公告）日：2011-11-17

  The present invention relates to pyrazine and pyridine compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula I wherein the variables are as defined herein.

  本发明涉及可用于作为ATR蛋白激酶抑制剂的吡嗪和吡啶化合物。本发明还涉及包含本发明化合物的药用可接受组合物；使用本发明化合物治疗各种疾病、障碍和状况的方法；制备本发明化合物的方法；制备本发明化合物的中间体；以及使用化合物进行体外应用的方法，例如研究生物和病理现象中的激酶；研究由这类激酶介导的细胞内信号转导途径；以及比较评估新的激酶抑制剂。本发明的化合物具有式I，其中变量如所定义。
• Asymmetric Total Synthesis of Twin Bufogargarizins A and B
  作者：Li-Ping Zhong、Rui Feng、Jing-Jing Wang、Chuang-Chuang Li

  DOI：10.1021/jacs.2c13494

  日期：2023.2.1

  The first and asymmetric total synthesis of bufogargarizins A and B, two unusual and highly oxygenated twin steroids with rearranged A/B rings, was achieved. The synthetically challenging [7–5–6–5] tetracyclic ring system of bufogargarizin A was efficiently constructed by the first intramolecular Ru-catalyzed [5 + 2] cycloaddition reaction of a vinyl ether cyclopropane-yne. Notably, the interesting

  bufogargarizins A 和 B 是两种不寻常且高度氧化的双类固醇，具有重排的 A/B 环，首次实现了不对称全合成。通过乙烯基醚环丙烷炔的第一个分子内 Ru 催化的 [5 + 2] 环加成反应，有效地构建了具有合成挑战性的 bufogargarizin A [7-5-6-5] 四环系统。值得注意的是，有趣的 [5-7-6-5] 蟾蜍加利津 B 四环骨架通过来自 [7-5-6-5] 四环框架的独特逆醛醇/跨环醛醇级联反应非对映选择性地重新组装。
• WO2006/120472
  申请人：——

  公开号：——

  公开（公告）日：——
• Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides
  作者：Philip J. Hilton、William McKinnon、Edward C. Gravett、Jean-Marie R. Peron、Christopher M. Frampton、M. Gary Nicholls、Gwyn Lord

  DOI：10.1016/j.steroids.2010.07.010

  日期：2010.12

  Partial inhibition of the sodium pump (Na/K-ATP-ase) by a circulating inhibitor is known to occur in humans. The objectives of this study were to determine the effects of novel bufadienolides lacking an oxygen at C14 on sodium pumps in human erythrocytes and leucocytes, dog kidney and pig brain and to document the importance of the stereochemistry at C17 on the ability to inhibit these sodium pumps. 14 alpha bufadienolides were weak inhibitors of all preparations studied. 3 beta-OH,5 beta,14 beta bufadienolide produced near-total inhibition of dog kidney and pig brain Na/K-ATP-ase. Over the same concentration range, it maximally inhibited the sodium pump of erythrocytes by 70% and leucocytes by 47%. The inhibition profile induced in the leucocyte sodium pump deviated significantly from the simple sigmoidal relationship present in the other preparations over the 3 x 10(-5) to 1 x 10(-7) mol/1 concentration range. Allo-emicymarin (17 alpha) was confirmed to be a weak inhibitor of the sodium pump/ATP-ase compared with emicymarin (17 beta) but both were weaker inhibitors of the leucocyte sodium pump than that of the other preparations. Molecules with the C14 in the beta configuration are more efficacious than in the a configuration. In the case of emicymarin, the attachment of the furone at C17 in the a configuration results in substantially weaker inhibitory activity than in the beta configuration, seen in most cardenolides and bufadienolides. Unlike ouabain and bufalin that show no specificity of action in these preparations, 3 beta-OH,5 beta,14 beta bufadienolide selectively inhibits the activity of at least one low-prevalence subset of the leucocyte Na/K-ATP-ase. (C) 2010 Elsevier Inc. All rights reserved.
• A New Route to 5-Aryl and 5-Heteroaryl-2-pyrones via Suzuki Coupling of a 2-Pyrone-5-boronate ester
  作者：Keith Jones、Edward C. Gravett、Philip J. Hilton、Jean-Marie Péron

  DOI：10.1055/s-2003-36789

  日期：——

  The synthesis of the 2-pyrone-5-boronate ester 5 is described along with its palladium-catalysed coupling reactions with a range of aryl and heteroaryl halides and triflates.

  本文介绍了 2-吡喃酮-5-硼酸酯 5 的合成及其与一系列芳基和杂芳基卤化物和三酸盐的钯催化偶联反应。