3-methylindole-7-boronic acid | 1284221-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-methylindole-7-boronic acid
• 英文别名: (3-methyl-1H-indol-7-yl)boronic acid
• CAS: 1284221-19-7
• 化学式: C₉H₁₀BNO₂
• 分子量: 174.995
• InChiKey: NHSYZQUXHSNCMM-UHFFFAOYSA-N

物化性质

• 沸点：
  430.2±37.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylindole-7-boronic acid 在 四(三苯基膦)钯 、 sodium acetate 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 30.0h， 生成 5,7-difluoro-2,2-dimethyl-6-(3-methyl-1H-indol-7-yl)-N-[(2-methylpropan-2-yl)oxy]-1,3-dihydroquinolin-4-imine
  参考文献：
  名称：

  Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation

  摘要：

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.104
• 作为产物：
  描述：

  3-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 在 二乙醇胺 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 0.83h， 生成 3-methylindole-7-boronic acid
  参考文献：
  名称：

  钯催化的（杂）芳基硼酸的烯丙基化

  摘要：

  异戊二烯基或二甲基烯丙基是天然产物和小分子治疗剂中常见的结构基序。在这份报告中，我们描述了钯催化的芳基和杂芳基硼酸与异戊二烯醇的交叉偶联方法。基于二烷基联芳基膦的催化剂体系对该转化具有很高的活性。这些辅助配体为调节碳-碳键形成的效率和区域选择性提供了机会。另外，该方法进一步扩展到对称的烯丙基醇与芳基硼酸的交叉偶联。

  DOI：

  10.1016/j.tetlet.2020.152800

文献信息

• Modulating the Electronic Structure of Cobalt in Molecular Catalysts via Coordination Environment Regulation for Highly Efficient Heterogeneous Nitrate Reduction
  作者：Libo Sun、Chencheng Dai、Tianjiao Wang、Xindie Jin、Zhichuan J. Xu、Xin Wang

  DOI：10.1002/anie.202320027

  日期：2024.4.8

  Macrocyclic molecular catalysts with different coordination environments were synthesized to enhance electrocatalytic nitrate reduction reaction (eNO3RR) for efficient ammonia (NH3) production. The best catalyst with N2(pyrrole)-N2(pyridine) configuration exhibited superior activity, achieving over 94 % NH3 Faradaic efficiency. The research highlights the impact of coordinating subunits on the electronic

  合成了具有不同配位环境的大环分子催化剂，以增强电催化硝酸盐还原反应（eNO 3 RR），以高效生产氨（NH 3 ）。具有N 2 (吡咯)-N 2 (吡啶)构型的最佳催化剂表现出优异的活性，实现了超过94%的NH 3法拉第效率。该研究强调了配位亚基对 eNO 3 RR 的电子结构和活性的影响，并建立了电子结构、实验活性和计算参数之间的相关性。
• Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation
  作者：Andrew R. Hudson、Robert I. Higuchi、Steven L. Roach、Lino J. Valdez、Mark E. Adams、Angie Vassar、Deepa Rungta、Peter M. Syka、Dale E. Mais、Keith B. Marschke、Lin Zhi

  DOI：10.1016/j.bmcl.2011.01.104

  日期：2011.3

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed prenylation of (hetero)aryl boronic acids
  作者：Jeffrey Leister、Darrian Chao、Kelvin L. Billingsley

  DOI：10.1016/j.tetlet.2020.152800

  日期：2021.3

  cross-coupling of aryl and heteroaryl boronic acids with prenyl alcohol. Catalyst systems based on dialkylbiaryl phosphines were highly active for this transformation. These supporting ligands provided opportunities for tuning the efficiency and regioselectivity of carbon–carbon bond formation. In addition, this method was further extended to the cross-coupling of symmetrical allylic alcohols with aryl boronic

  异戊二烯基或二甲基烯丙基是天然产物和小分子治疗剂中常见的结构基序。在这份报告中，我们描述了钯催化的芳基和杂芳基硼酸与异戊二烯醇的交叉偶联方法。基于二烷基联芳基膦的催化剂体系对该转化具有很高的活性。这些辅助配体为调节碳-碳键形成的效率和区域选择性提供了机会。另外，该方法进一步扩展到对称的烯丙基醇与芳基硼酸的交叉偶联。