3-(4-hydroxybenzoyl)benzonitrile | 118909-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-hydroxybenzoyl)benzonitrile
• 英文别名: 4-(3-cyanobenzoyl)phenol；3-cyano-4'-hydroxy-benzophenone；3-Cyanophenyl 4-hydroxyphenyl methanone
• CAS: 118909-04-9
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: RVBPKXNAHYSUGP-UHFFFAOYSA-N

物化性质

• 熔点：
  153-157 °C
• 沸点：
  438.7±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxybenzoyl)benzonitrile 在 三正丁基叠氮化锡 、 potassium tert-butylate 、 sodium iodide 作用下， 以 乙醇 、 乙二醇二乙醚 为溶剂， 反应 126.0h， 生成 1-[2-hydroxy-3-propyl-4-({4-[3-(1H-tetrazol-5-yl)benzoyl]phenoxy}methyl)phenyl]ethanone
  参考文献：
  名称：

  (Phenylmethoxy)phenyl derivatives of w-oxo- and w-tetrazolylalkanoic acids and related tetrazoles. Synthesis and evaluation as leukotriene D4 receptor antagonists

  摘要：

  Two series of (phenylmethoxy)phenyl compounds derived from the structure of LY163443 were synthesized and evaluated as leukotriene D4 receptor antagonists. In the OMEGA-[(phenylmethoxy)phenyl]-OMEGA-oxoalkanoic acid series, 5-[4-[(4-acetyl-2-ethyl-3-hydroxyphenyl)methoxy]phenyl]-3,3-dimethyl-5-oxopentanoic acid (8) was the most potent antagonist of LTD4-induced contractions of guinea pig ileum (pK(B) of 7.60) and LTD4 pressor response in pithed rats (ED50 of 1.4 mg/kg iv). Replacing the carboxylic acid function with 5-tetrazole gave slightly more potent compounds. In the OMEGA-[5-[[(phenylmethoxy)phenyl]alkyl]tetrazolyl]alkanoic acid series, replacing the carboxylic acid with 5-tetrazole gave compounds that were equally effective in the guinea pig ileum but more potent in vivo against the LTD4 pressor response in rat. The pK(B) value in the guinea pig ileum for 1-[2-hydroxy-3-propyl-4-[[4-[[2-[3-(1H-tetrazol-5-yl)propyl]-2H-tetrazol-5-yl]methyl]phenoxy]methyl]phenyl]ethanone (25) was 7.87 and the ED50 for antagonism of the LTD4 pressor response was 4.0 mg/kg iv. The sodium salts of 8 (9) and 25 (26) given by the iv route of administration antagonized LTD4-induced cardiovascular alterations in anesthetized rat and LTD4-induced bronchoconstriction in guinea pig in a dose-dependent manner. Oral activity was also demonstrated against the LTD4-induced bronchoconstriction in guinea pig.

  DOI：

  10.1021/jm00113a014
• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)苯甲腈 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 以2 g的产率得到3-(4-hydroxybenzoyl)benzonitrile
  参考文献：
  名称：

  二苯甲酮类化合物及其制备方法和应用

  摘要：

  本申请提供了一种二苯甲酮类化合物或其药学上可接受的盐，其结构如式I所示： 其中，X为‑(C＝O)‑NH‑或‑NH‑(C＝O)‑；n为1‑10的整数；R1、R2、R3分别表示一个或多个取代基，多个取代基可相同或不同，R1、R2、R3各自独立地选自氢、卤素、C1‑5烷基、C1‑5烷氧基、羟基、硝基、氰基和氨基中的一个或多个。本发明的化合物能够调控Kv11.1通道，恢复或逆转阿司咪唑对Kv11.1通道的抑制作用，降低阿司咪唑的心脏毒性以及具有缓解获得性LQTS的药学活性，是治疗获得性LQTS的潜在药物。

  公开号：

  CN115611805A

文献信息

• Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C≡C Triple Bond Cleavage
  作者：Arunachalam Sagadevan、Vaibhav Pramod Charpe、Ayyakkannu Ragupathi、Kuo Chu Hwang

  DOI：10.1021/jacs.6b13113

  日期：2017.3.1

  Direct oxidative coupling of phenols and terminal alkynes was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox process. This method allows regioselective synthesis of hydroxyl-functionalized aryl and alkyl ketones from simple phenols and phenylacetylene via C≡C triple bond cleavage. 47 examples were presented. From a synthetic perspective, this protocol offers an

  通过可见光介导的铜催化光氧化还原过程，在室温下实现了酚类和末端炔烃的直接氧化偶联。该方法允许通过 C≡C 三键断裂从简单的苯酚和苯乙炔区域选择性合成羟基官能化的芳基酮和烷基酮。展示了 47 个例子。从合成的角度来看，该协议为制备药物（如匹托苯和非诺贝特）提供了一种有效的合成途径。
• Leukotriene antagonists and use thereas
  申请人：Eli Lilly and Company

  公开号：US04853398A1

  公开（公告）日：1989-08-01

  This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.

  这项发明提供了苯乙烯衍生物，这些衍生物是白三烯拮抗剂，以及这些衍生物的配方，以及使用这些衍生物治疗由白三烯过度释放引起的疾病的方法。
• Novel beta-d-phenylthioxylosides, their method of preparation and their
  申请人：Fournier Innovation et Synergie

  公开号：US04996347A1

  公开（公告）日：1991-02-26

  The present invention relates, by way of novel industrial products, to osides selected from the group consisting of: (i) the .beta.-.eta.-phenylthioxylosides of the formula: ##STR1## in which: R represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, A represents the sulfur atom or the oxygen atom, B represents a CH.sub.2, CHOH or CO group and Y represents the hydrogen atom or an acyl group; and (ii) epimers thereof when B is CHOH. These products are useful in therapy as antithrombotics.

  本发明涉及一种新型工业产品，即从以下组中选择的糖苷：（i）式为：##STR1##其中：R代表氢原子、卤素原子、硝基或氰基，A代表硫原子或氧原子，B代表CH.sub.2、CHOH或CO基团，Y代表氢原子或酰基团；以及（ii）当B为CHOH时的对映体。这些产品在治疗中作为抗血栓剂有用。
• Novel .beta.-D-phenylthioxylosides, their method of preparation and
  申请人：Fournier Innovation et Synergie

  公开号：US04877808A1

  公开（公告）日：1989-10-31

  The present invention relates, by way of novel industrial products, to osides selected from the group consisting of: (i) the .beta.-D-phenylthioxylosides of the formula: ##STR1## in which: R represents a hydrogen atom, a halogen atom, a nitro group or a cyano group, A represents the sulfur atom or the oxygen atom, B represents a CH.sub.2, CHOH or CO group and Y represents the hydrogen atom or an acyl group; and (ii) epimers thereof when B is CHOH. These products are useful in therapy as antithrombotics.

  本发明涉及一种新型工业产品，其中所述的奥糖被选择自组中的β-D-苯硫氧基木糖苷，其化学式为：##STR1## 其中：R代表氢原子、卤素原子、硝基或氰基，A代表硫原子或氧原子，B代表CH.sub.2、CHOH或CO基团，Y代表氢原子或酰基；以及当B为CHOH时的对映异构体。这些产品在治疗中作为抗血栓药物具有用处。
• 二苯甲酮类化合物及其制备方法和应用
  申请人：山东大学

  公开号：CN115611805A

  公开（公告）日：2023-01-17

  本申请提供了一种二苯甲酮类化合物或其药学上可接受的盐，其结构如式I所示： 其中，X为‑(C＝O)‑NH‑或‑NH‑(C＝O)‑；n为1‑10的整数；R1、R2、R3分别表示一个或多个取代基，多个取代基可相同或不同，R1、R2、R3各自独立地选自氢、卤素、C1‑5烷基、C1‑5烷氧基、羟基、硝基、氰基和氨基中的一个或多个。本发明的化合物能够调控Kv11.1通道，恢复或逆转阿司咪唑对Kv11.1通道的抑制作用，降低阿司咪唑的心脏毒性以及具有缓解获得性LQTS的药学活性，是治疗获得性LQTS的潜在药物。