苯并呋喃-2-硼酸甲基亚氨基二乙酸酯 | 1104637-65-1

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 苯并呋喃-2-硼酸甲基亚氨基二乙酸酯
• 英文名称: benzofuran-2-MIDA boronate
• 英文别名: 2-benzofuranylboronicacid MIDA ester；2-(1-Benzofuran-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione；2-(1-benzofuran-2-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
• CAS: 1104637-65-1
• 化学式: C₁₃H₁₂BNO₅
• 分子量: 273.053
• InChiKey: ASPDKYQZQMDSKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  198-202 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  苯并呋喃-2-硼酸甲基亚氨基二乙酸酯 、 3'-溴苯乙酮 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以93%的产率得到2-(3-acetylphenyl)benzo[b]furan
  参考文献：
  名称：

  Cyrene 作为 Suzuki-Miyaura 交叉偶联的生物基溶剂

  摘要：

  Suzuki-Miyaura (SM) 交叉偶联是化学工业中使用最广泛的 Pd 催化的 C-C 键形成反应。大部分 SM 偶联剂使用偶极非质子溶剂；然而，当前的可持续性举措和日益严格的法规提倡使用具有更理想特性的替代品。在这里，我们描述了生物衍生溶剂 Cyrene™ 在 SM 交叉偶联中的范围和效用，并评估其作为反应介质的适用性，以实现从发现到克级规模的这一基准转化。

  DOI：

  10.1055/s-0036-1589143
• 作为产物：
  描述：

  2-碘苯酚 、 乙炔基硼酸甲基亚氨基二乙酸酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 、 四甲基胍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以60%的产率得到苯并呋喃-2-硼酸甲基亚氨基二乙酸酯
  参考文献：
  名称：

  Tandem Sonogashira-Hagihara Coupling/Cycloisomerization Reactions of Ethynylboronic Acid MIDA Ester to Afford 2-Heterocyclic Boronic Acid MIDA Esters: A Concise Route to Benzofurans, Indoles, Furopyridines and Pyrrolopyridines

  摘要：

  A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.

  DOI：

  10.3987/com-17-13723

文献信息

• Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics
  作者：Joseph Cameron、Mahmoud Matar Abed、Steven J. Chapman、Neil J. Findlay、Peter J. Skabara、Peter N. Horton、Simon J. Coles

  DOI：10.1039/c7tc05075e

  日期：——

  Subtle changes in the choice of the chalcogen atom in benzochalcogenadiazole ‘small molecules’ can lead to a marked difference in the PCE of bulk heterojunction organic solar cells.

  在苯基硫属、硒属二唑“小分子”中选择硫属原子的微小变化，可以导致有机太阳能电池的体异质结光电转换效率（PCE）的显著差异。
• Simplified Preparation of ppm Pd-Containing Nanoparticles as Catalysts for Chemistry in Water
  作者：Yuting Hu、Xiaohan Li、Gongzhen Jin、Bruce H. Lipshutz

  DOI：10.1021/acscatal.3c00007

  日期：2023.3.3

  different types of couplings are studied: Suzuki–Miyaura, Sonogashira, Mizoroki–Heck, and Negishi reactions, all performed under mild aqueous micellar conditions. The simplified process relies on the initial formation of stable, storable Pd- and ligand-free NPs, to which is then added the appropriate amount of Pd(OAc)2 and ligand-matched to the desired type of coupling, in water.

  已经开发了一种协议，它不仅简化了纳米粒子 (NPs) 的制备，纳米粒子 (NPs) 含有 ppm 水平的连接钯，影响多相催化，而且由于每种试剂的新制备性质，还确保它们可重复地提供交叉耦合的产品。研究了四种不同类型的偶联：Suzuki–Miyaura、Sonogashira、Mizoroki–Heck 和 Negishi 反应，所有反应均在温和的水性胶束条件下进行。简化的过程依赖于稳定、可储存的无 Pd 和无配体 NP 的初始形成，然后在水中加入适量的 Pd(OAc) 2和配体匹配到所需的偶联类型。
• Species-Selective Pyrimidineamine Inhibitors of <i>Trypanosoma brucei S</i>-Adenosylmethionine Decarboxylase
  作者：Oleg A. Volkov、Anthony J. Brockway、Stephen A. Wring、Michael Peel、Zhe Chen、Margaret A. Phillips、Jef K. De Brabander

  DOI：10.1021/acs.jmedchem.7b01654

  日期：2018.2.8

  New therapeutic options are needed for treatment of human African trypanosomiasis (HAT) caused by protozoan parasite Trypanosoma brucei. S-Adenosylmethionine decarboxylase (AdoMetDC) is an essential enzyme in the polyamine pathway of T. brucei. Previous attempts to target this enzyme were thwarted by the lack of brain penetration of the most advanced series. Herein, we describe a T. brucei AdoMetDC inhibitor series based on a pyrimidineamine pharmacophore that we identified by target-based high-throughput screening. The pyrimidineamines showed selectivity for T. brucei AdoMetDC over the human enzyme, inhibited parasite growth in whole-cell assay, and had good predicted blood-brain barrier penetration. The medicinal chemistry program elucidated structure-activity relationships within the series. Features of the series that were required for binding were revealed by determining the X-ray crystal structure of TbAdoMetDC bound to one analog. The pyrimidineamine series provides a novel starting point for an anti-HAT lead optimization.
• Tandem Sonogashira-Hagihara Coupling/Cycloisomerization Reactions of Ethynylboronic Acid MIDA Ester to Afford 2-Heterocyclic Boronic Acid MIDA Esters: A Concise Route to Benzofurans, Indoles, Furopyridines and Pyrrolopyridines
  作者：Yohji Sakurai

  DOI：10.3987/com-17-13723

  日期：——

  A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.
• Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-Coupling
  作者：Allan Watson、Kirsty Wilson、Jane Murray、Craig Jamieson

  DOI：10.1055/s-0036-1589143

  日期：2018.3

  reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene™ in SM cross-couplings and evaluate its suitability as a reaction medium

  Suzuki-Miyaura (SM) 交叉偶联是化学工业中使用最广泛的 Pd 催化的 C-C 键形成反应。大部分 SM 偶联剂使用偶极非质子溶剂；然而，当前的可持续性举措和日益严格的法规提倡使用具有更理想特性的替代品。在这里，我们描述了生物衍生溶剂 Cyrene™ 在 SM 交叉偶联中的范围和效用，并评估其作为反应介质的适用性，以实现从发现到克级规模的这一基准转化。