2-(4-甲氧基苯基)-6-甲基-1,3,6,2-二氧氮杂环硼辛烷-4,8-二酮 | 1257739-11-9

• 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
• 中文名称: 2-(4-甲氧基苯基)-6-甲基-1,3,6,2-二氧氮杂环硼辛烷-4,8-二酮
• 英文名称: 2-(4-methoxyphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• 英文别名: 2-(4-Methoxyphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• CAS: 1257739-11-9
• 化学式: C₁₂H₁₄BNO₅
• 分子量: 263.058
• InChiKey: UMYGAOMZGXRKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-6-甲基-1,3,6,2-二氧氮杂环硼辛烷-4,8-二酮 、 5-碘嘧啶 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以93%的产率得到5-(4-甲氧基苯基)嘧啶
  参考文献：
  名称：

  A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam

  摘要：

  Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized siliceous mesocellular foam are presented. The nanopalladium catalyst effectively couples not only heteroaryl halides with boronic acids but also heteroaryl halides with boronate esters, potassium trifluoroborates, MIDA boronates, and triolborates, producing a wide range of heterobiaryls in good to excellent yields. Furthermore, the heterogeneous palladium nanocatalyst can easily be removed from the reaction mixture by filtration and recycled several times with minimal loss in activity. This catalyst provides an alternative, environmentally friendly, low-leaching process for the preparation of heterobiaryls.

  DOI：

  10.1021/jo500409r
• 作为产物：
  描述：

  N-甲基亚氨二乙酸 、 4-甲氧基苯硼酸 130.0 ℃ 、1.72 MPa 条件下， 反应 0.08h， 以70%的产率得到2-(4-甲氧基苯基)-6-甲基-1,3,6,2-二氧氮杂环硼辛烷-4,8-二酮
  参考文献：
  名称：

  Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

  摘要：

  A library of over 20, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates have been synthesised. A rapid microwave-mediated (MW) method (5-10 min) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.044

文献信息

• Highly Functionalized Biaryls via Suzuki-Miyaura Cross-Coupling Catalyzed by Pd@MOF under Batch and Continuous Flow Regimes
  作者：Vlad Pascanu、Peter R. Hansen、Antonio Bermejo Gómez、Carles Ayats、Ana E. Platero-Prats、Magnus J. Johansson、Miquel À. Pericàs、Belén Martín-Matute

  DOI：10.1002/cssc.201402858

  日期：2015.1

  currently existing commercial procedures. Most importantly, Pd@MIL‐101‐NH2 was packed in a micro‐flow reactor, which represents the first report of metallic nanoparticles supported on MOFs employed in flow chemistry for catalytic applications. A small library of 11 isolated compounds was created in a continuous experiment without replacing the catalyst, demonstrating the potential of the catalyst for large‐scale

  通过在功能化介孔MOF（8 wt％Pd @ MIL-101（Cr）-NH 2）中负载的Pd纳米粒子催化的Suzuki-Miyaura交叉偶联反应，成功合成了多种多样的40多种高度官能化的联芳基。尽管存在各种官能团和/或几个杂原子，但可以在迄今报道的某些最温和的条件下实现这一目标，并且可以保持对金属物种浸出的强有力控制。一些目标分子是药物合成中的重要中间体，我们清楚地举例说明了该催化系统的多功能性，与当前现有的商业程序相比，该催化系统的收率更高。最重要的是，Pd @ MIL-101-NH 2将其装在微流反应器中，这代表了在流化学中用于催化应用的MOF上负载的金属纳米颗粒的首次报道。在不替换催化剂的情况下，通过连续实验创建了一个11个分离的化合物的小型文库，证明了该催化剂在大规模应用中的潜力。
• Furo[3,2‐<i>b</i>]pyridine: A Privileged Scaffold for Highly Selective Kinase Inhibitors and Effective Modulators of the Hedgehog Pathway
  作者：Václav Němec、Michaela Hylsová、Lukáš Maier、Jana Flegel、Sonja Sievers、Slava Ziegler、Martin Schröder、Benedict‐Tilman Berger、Apirat Chaikuad、Barbora Valčíková、Stjepan Uldrijan、Stanislav Drápela、Karel Souček、Herbert Waldmann、Stefan Knapp、Kamil Paruch

  DOI：10.1002/anie.201810312

  日期：2019.1.21

  of the furo[3,2‐b]pyridine core as a novel scaffold for potent and highly selective inhibitors of cdc‐like kinases (CLKs) and efficient modulators of the Hedgehog signaling pathway. Initially, a diverse target compound set was prepared by synthetic sequences based on chemoselective metal‐mediated couplings, including assembly of the furo[3,2‐b]pyridine scaffold by copper‐mediated oxidative cyclization

  据报道，呋喃[3,2-b]吡啶核是一种新型的支架，可作为有效且高度选择性的cdc-like激酶（CLKs）抑制剂和刺猬信号通路的有效调节剂。最初，基于化学选择性金属介导的偶联，通过合成序列制备了多样化的目标化合物，包括通过铜介导的氧化环化组装呋喃[3,2-b]吡啶骨架。含有3,5-二取代的呋喃[3,2-b]吡啶的亚系列的优化提供了有效的，细胞活性的和高度选择性的CLKs抑制剂。对3,5,7-三取代的呋喃并[3,2-b]吡啶的激酶无活性子集的分析揭示了Hedgehog途径的亚微摩尔调节剂。
• Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates
  作者：Adam J. Close、Paul Kemmitt、Matthew K. Emmerson、John Spencer

  DOI：10.1016/j.tet.2014.09.044

  日期：2014.11

  A library of over 20, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates have been synthesised. A rapid microwave-mediated (MW) method (5-10 min) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.
• A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam
  作者：Emma Bratt、Oscar Verho、Magnus J Johansson、Jan-Erling Bäckvall

  DOI：10.1021/jo500409r

  日期：2014.5.2

  Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized siliceous mesocellular foam are presented. The nanopalladium catalyst effectively couples not only heteroaryl halides with boronic acids but also heteroaryl halides with boronate esters, potassium trifluoroborates, MIDA boronates, and triolborates, producing a wide range of heterobiaryls in good to excellent yields. Furthermore, the heterogeneous palladium nanocatalyst can easily be removed from the reaction mixture by filtration and recycled several times with minimal loss in activity. This catalyst provides an alternative, environmentally friendly, low-leaching process for the preparation of heterobiaryls.