4-(2’-氯苄氧基)-3,5-二甲基苯基硼酸 | 849052-15-9

• 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 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(2’-氯苄氧基)-3,5-二甲基苯基硼酸
• 中文别名: 4-(2'-氯苄氧基)-3,5-二甲基苯基硼酸
• 英文名称: 4-(2'-chlorobenzyloxy)-3,5-dimethylphenylboronic acid
• 英文别名: [4-[(2-chlorophenyl)methoxy]-3,5-dimethylphenyl]boronic acid
• CAS: 849052-15-9
• 化学式: C₁₅H₁₆BClO₃
• 分子量: 290.554
• InChiKey: UDKYOMYSPIEDTK-UHFFFAOYSA-N

物化性质

• 熔点：
  234-238 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H413

反应信息

• 作为反应物：
  描述：

  4-(2’-氯苄氧基)-3,5-二甲基苯基硼酸 在 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L₃P] ³⁺: Applications in Pt(II) Catalysis

  摘要：

  Reaction of tris(dimethylaminocyclopropenium) substituted phosphine 1 with K2PtCl4 afforded the bench stable complex 3 which upon treatment with Ag[CB11H6Cl6] turned out to be an excellent catalyst for the transformation of a variety of ortho-biaryl substituted alkynes into polycyclic homo- and heteroarenes of different size, shape, and curvature through a 6-endo-dig cyclization. This constitutes the first example ever reported of using a P-1-centered trication as ligand in catalysis. The strong pi-acceptor character of 1 that derives from its three positive charges substantially increases the intrinsic pi-acidity of Pt in complex 1.PtCl2 and dramatically enhances its ability to activate pi-systems toward nucleophilic attack. As a consequence, a remarkable acceleration of the model transformation is observed when compared with other classical pi-acceptor ligands such as P(OPh)(3) or P(C6F5)(3). Moreover, the employment of 1 as ligand also expands the scope of this reaction to previously inaccessible substitution patterns. Kinetic studies and deuterium labeling experiments as well as density functional theory (DFT) calculations were performed in order to explain these findings.

  DOI：

  10.1021/ja306947m

文献信息

• Polysubstituted Pyrimidines as mPGES‐1 Inhibitors: Discovery of Potent Inhibitors of PGE ₂ Production with Strong Anti‐inflammatory Effects in Carrageenan‐Induced Rat Paw Edema
  作者：Filip Kalčic、Viktor Kolman、Haresh Ajani、Zdeněk Zídek、Zlatko Janeba

  DOI：10.1002/cmdc.202000258

  日期：2020.8.5

  These compounds are sub‐micromolar inhibitors of PGE2 production (IC50 as low as 12 nM). In order to identify the molecular target of anti‐inflammatory pyrimidines, we performed extensive studies including enzymatic assays, homology modeling and docking. The difluorinated analogue simultaneously inhibits two key enzymes of the arachidonic acid cascade, namely mPGES‐1 and COX‐2, with mPGES‐1 inhibition

  我们报道了对多取代嘧啶进行的广泛的构效关系优化，从而发现了5-丁基-4-（4-苄氧基苯基）-6-苯基嘧啶-2-胺及其二氟类似物。这些化合物是PGE 2产生的亚微摩尔抑制剂（IC 50低至12 nM）。为了确定抗炎嘧啶的分子靶标，我们进行了广泛的研究，包括酶法测定，同源性建模和对接。二氟类似物同时抑制花生四烯酸级联的两个关键酶，即mPGES-1和COX-2，其中mPGES-1的抑制是主要的作用机理。研究的其他嘧啶类是有效的mPGES-1抑制剂，没有观察到对COX-1 / 2酶的抑​​制作用。此外，在急性炎症模型中，两种最有效的化合物在体内被证明是有效的，将角叉菜胶诱导的大鼠爪水肿抑制了36％和46％。这项研究的有希望的结果值得对所选的抗炎候选药物进行进一步的临床前评估。