苯并[D]噁唑-2-羧酸钾 | 119130-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 苯并[D]噁唑-2-羧酸钾
• 英文名称: potassium benzo[d]oxazole-2-carboxylate
• 英文别名: Potassium 1,3-benzoxazole-2-carboxylate；potassium;1,3-benzoxazole-2-carboxylate
• CAS: 119130-94-8
• 化学式: C₈H₄NO₃*K
• 分子量: 201.223
• InChiKey: BJRBWXXVOQASLD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯并[D]噁唑-2-羧酸钾 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 以97.5 %的产率得到1,3-苯并恶唑-2-甲酰氯
  参考文献：
  名称：

  A general chemical principle for creating closure-stabilizing integrin inhibitors

  摘要：

  DOI：

  10.1016/j.cell.2022.08.008
• 作为产物：
  描述：

  苯并[d]噁唑-2-羧酸甲酯 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以98%的产率得到苯并[D]噁唑-2-羧酸钾
  参考文献：
  名称：

  用于OLED的新型hetero杂芳族羧酸酯的设计

  摘要：

  提出了定向合成镧系元素芳族羧酸盐（电致发光材料的前体）的方法，即增加共轭长度和在适当位置结合中性配体引入杂原子。这导致了一系列新的镧系元素络合物的分离，其中在溶液加工的OLED中混合配体苯并噻唑-2-羧酸carboxy与邻菲咯啉获得了最高的电致发光效率。能量传递过程的特殊性允许获得基于该系统的发光温度计材料，这在生理范围内使灵敏度降低了2.8％/ K。

  DOI：

  10.1016/j.dyepig.2019.107604

文献信息

• C–H carboxylation of heteroarenes with ambient CO₂
  作者：Sabine Fenner、Lutz Ackermann

  DOI：10.1039/c6gc00200e

  日期：——

  The C-H carboxylation of heteroarenes was achieved under transition metal-free reaction conditions with naturally abundant CO2 as the C1 source at relatively low temperature.

  杂芳烃的CH羧化反应是在无过渡金属的反应条件下进行的，在相对较低的温度下以自然丰富的CO 2作为C1源。
• Copper-Catalyzed Direct Carboxylation of CH Bonds with Carbon Dioxide
  作者：Liang Zhang、Jianhua Cheng、Takeshi Ohishi、Zhaomin Hou

  DOI：10.1002/anie.201003995

  日期：2010.11.8

  Cooking with gas: Copper complexes serve as excellent catalysts for the direct carboxylation of aromatic heterocyclic CH bonds with CO2, thereby offering an economical and environmentally benign process for the synthesis of heterocyclic carboxylic esters (see scheme; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene). Some active intermediates of this reaction have been isolated and structurally

  天然气烹饪：铜络合物是出色的催化剂，可将芳族杂环CH键与CO 2直接羧化，从而为杂环羧酸酯的合成提供了一种经济，环境友好的工艺（请参见方案; IPr = 1,3-双（2,6-二异丙基苯基）咪唑-2-亚基）。已经分离出该反应的一些活性中间体并对其结构进行了表征。
• Carboxylic Acid Salts as Dual‐Function Reagents for Carboxylation and Carbon Isotope Labeling
  作者：Shuo Wang、Igor Larrosa、Hideki Yorimitsu、Gregory J. P. Perry

  DOI：10.1002/anie.202218371

  日期：2023.3.27

  The potassium salt of triphenylacetic acid is developed as a combined source of CO2 and base/metalating agent. This method avoids specialized equipment and is used in the carboxylation of a range of compound classes. This provides a mechanistically distinct approach to carboxylation that has also been applied in carbon isotope labeling.

  三苯乙酸的钾盐被开发为 CO 2和碱/金属化剂的组合来源。该方法无需专用设备，可用于一系列化合物类别的羧化。这提供了一种机械上不同的羧化方法，该方法也已应用于碳同位素标记。
• Structure–Activity Study of <i>N</i>-((<i>trans</i>)-4-(2-(7-Cyano-3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)ethyl)cyclohexyl)-1<i>H</i>-indole-2-carboxamide (SB269652), a Bitopic Ligand That Acts as a Negative Allosteric Modulator of the Dopamine D₂ Receptor
  作者：Jeremy Shonberg、Christopher Draper-Joyce、Shailesh N. Mistry、Arthur Christopoulos、Peter J. Scammells、J. Robert Lane、Ben Capuano

  DOI：10.1021/acs.jmedchem.5b00581

  日期：2015.7.9

  We recently demonstrated that 5B269652 (1) engages one protomer of a dopamine D-2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, we investigate structural determinants for allostery, focusing on modifications to three moieties within 1. We find that orthosteric "head" groups with small 7-substituents were important to maintain the limited negative cooperativity of analogues of 1, and replacement of the tetrahydroisoquinoline head group with other D2R "privileged structures" generated orthosteric antagonists. Additionally, replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacology. We validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining negative cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as negative allosteric modulators of the D2R.
• Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand
  作者：Shailesh N. Mistry、Jeremy Shonberg、Christopher J. Draper-Joyce、Carmen Klein Herenbrink、Mayako Michino、Lei Shi、Arthur Christopoulos、Ben Capuano、Peter J. Scammells、J. Robert Lane

  DOI：10.1021/acs.jmedchem.5b00585

  日期：2015.9.10

  Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)-ethyl)cyclohexyl)-1H-indole-2-carboxamide (0269652) (1) adopts a bitopic pose at one protomer of a dopamine D-2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.