4-(2-甲氧基苯基)苯基硼酸频哪醇酯 | 881314-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-甲氧基苯基)苯基硼酸频哪醇酯
• 英文名称: 2-(2'-methoxy-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[4-(2-Methoxyphenyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 881314-65-4
• 化学式: C₁₉H₂₃BO₃
• 分子量: 310.201
• InChiKey: UMZWOISFJWYEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-(2-甲氧基苯基)苯基硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tin(II) chloride dihdyrate 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 47.17h， 生成 methyl 5-((6-chloro-5-(2'-methoxy-[1,1'-biphenyl]-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoate
  参考文献：
  名称：

  Structural Determinants for Small-Molecule Activation of Skeletal Muscle AMPK α2β2γ1 by the Glucose Importagog SC4

  摘要：

  The AMP-activated protein kinase (AMPK) alpha beta gamma het-erotrimer regulates cellular energy homeostasis with tissue-specific isoform distribution. Smallmolecule activation of skeletal muscle alpha 2 beta 2 AMPK complexes may prove a valuable treatment strategy for type 2 diabetes and insulin resistance. Herein, we report the small-molecule SC4 is a potent, direct AMPK activator that preferentially activates alpha 2 complexes and stimulates skeletal muscle glucose uptake. In parallel with the term secretagog, we propose "importagog" to define a substance that induces or augments cellular uptake of another substance. Three-dimensional structures of the glucose importagog SC4 bound to activated alpha 2 beta 2 gamma 1 and alpha 2 beta 1 gamma 1 complexes reveal binding determinants, in particular a key interaction between the SC4 imidazopyridine 4'-nitrogen and beta 2-Asp111, which provide a design paradigm for beta 2-AMPK therapeutics. The alpha 2 beta 2 gamma 1/SC4 structure reveals an interaction between a beta 2 N-terminal alpha helix and the alpha 2 autoinhibitory domain. Our results provide a structurefunction guide to accelerate development of potent, but importantly tissue-specific, beta 2-AMPK therapeutics.

  DOI：

  10.1016/j.chembiol.2018.03.008
• 作为产物：
  描述：

  1-氟-4-(2-甲氧基苯基)苯 、 联硼酸频那醇酯 在 四甲基乙二胺 、 iron(II) chloride 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以70%的产率得到4-(2-甲氧基苯基)苯基硼酸频哪醇酯
  参考文献：
  名称：

  将LiHMDS促进的钯和铁催化本位芳氟化物-Defluoroborylation

  摘要：

  提出了一种在LiHMDS存在下，通过芳基氟化物与双（频哪醇）二硼（B 2 pin 2）的钯或铁催化的交叉偶联反应合成芳基硼酸频哪醇酯的新方法。Pd催化的氟代芳烃的脱氟硼化与各种官能团兼容，例如伯胺和仲胺，酮，三氟甲基，烷氧基和硼基。显着地，不需要外部配体来提高转化效率。

  DOI：

  10.1021/acs.orglett.8b02228

文献信息

• Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides
  作者：Ting-Feng Wu、Yue-Jiao Zhang、Yue Fu、Fang-Jie Liu、Jian-Tao Tang、Peng Liu、F. Dean Toste、Baihua Ye

  DOI：10.1016/j.chempr.2021.06.007

  日期：2021.7

  palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity

  过渡金属催化的交叉亲电偶联 (XEC) 是锻造 C(sp 2 )–C(sp 2 ) 的有力工具) 联芳基分子中来自丰富芳族卤化物的键。虽然通过多金属 XEC 合成不对称联芳基化合物具有很高的合成价值，但两种杂芳族卤化物的选择性 XEC 仍然难以捉摸且具有挑战性。在这里，我们报告了一种均相 XEC 方法，该方法依赖于锆氮丙啶配合物作为双钯催化过程的穿梭。锆氮丙啶介导的钯 (ZAPd) 催化反应显示出与各种官能团和各种杂芳族支架的良好相容性。根据密度泛函理论 (DFT) 计算，氧化加成产物和锆氮丙啶之间的氧化还原金属转移被认为是关键的基本步骤。因此，使用单一过渡金属催化剂的交叉偶联选择性由 Pd(0) 氧化加成到芳族卤化物的相对速率控制。总体而言，组合还原剂和金属转移剂的概念为过渡金属还原偶联催化的发展提供了机会。
• [EN] PHENYL-SUBSTITUTED QUINOLINE AND QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF DIABETES<br/>[FR] COMPOSES A BASE DE QUINOLEINE ET DE QUINAZOLINE A SUBSTITUTION PHENYLIQUE POUR LE TRAITEMENT DU DIABETE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2006034491A3

  公开（公告）日：2006-08-24
• Structural Determinants for Small-Molecule Activation of Skeletal Muscle AMPK α2β2γ1 by the Glucose Importagog SC4
  作者：Kevin R.W. Ngoei、Christopher G. Langendorf、Naomi X.Y. Ling、Ashfaqul Hoque、Swapna Varghese、Michelle A. Camerino、Scott R. Walker、Ylva E. Bozikis、Toby A. Dite、Ashley J. Ovens、William J. Smiles、Roxane Jacobs、He Huang、Michael W. Parker、John W. Scott、Mark H. Rider、Richard C. Foitzik、Bruce E. Kemp、Jonathan B. Baell、Jonathan S. Oakhill

  DOI：10.1016/j.chembiol.2018.03.008

  日期：2018.6

  The AMP-activated protein kinase (AMPK) alpha beta gamma het-erotrimer regulates cellular energy homeostasis with tissue-specific isoform distribution. Smallmolecule activation of skeletal muscle alpha 2 beta 2 AMPK complexes may prove a valuable treatment strategy for type 2 diabetes and insulin resistance. Herein, we report the small-molecule SC4 is a potent, direct AMPK activator that preferentially activates alpha 2 complexes and stimulates skeletal muscle glucose uptake. In parallel with the term secretagog, we propose "importagog" to define a substance that induces or augments cellular uptake of another substance. Three-dimensional structures of the glucose importagog SC4 bound to activated alpha 2 beta 2 gamma 1 and alpha 2 beta 1 gamma 1 complexes reveal binding determinants, in particular a key interaction between the SC4 imidazopyridine 4'-nitrogen and beta 2-Asp111, which provide a design paradigm for beta 2-AMPK therapeutics. The alpha 2 beta 2 gamma 1/SC4 structure reveals an interaction between a beta 2 N-terminal alpha helix and the alpha 2 autoinhibitory domain. Our results provide a structurefunction guide to accelerate development of potent, but importantly tissue-specific, beta 2-AMPK therapeutics.
• LiHMDS-Promoted Palladium or Iron-Catalyzed <i>ipso</i>-Defluoroborylation of Aryl Fluorides
  作者：Xianghu Zhao、Mingsheng Wu、Yisen Liu、Song Cao

  DOI：10.1021/acs.orglett.8b02228

  日期：2018.9.21

  A novel and efficient method for the synthesis of arylboronic acid pinacol esters via a palladium- or iron-catalyzed cross-coupling reaction of aryl fluorides with bis(pinacolato)diboron (B2pin2) in the presence of LiHMDS was developed. The Pd-catalyzed defluoroborylation of fluoroarenes is compatible with a variety of functional groups such as primary and secondary amine, ketone, trifluoromethyl,

  提出了一种在LiHMDS存在下，通过芳基氟化物与双（频哪醇）二硼（B 2 pin 2）的钯或铁催化的交叉偶联反应合成芳基硼酸频哪醇酯的新方法。Pd催化的氟代芳烃的脱氟硼化与各种官能团兼容，例如伯胺和仲胺，酮，三氟甲基，烷氧基和硼基。显着地，不需要外部配体来提高转化效率。