4-hydroxyphenyl 2-thienyl ketone | 38281-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyphenyl 2-thienyl ketone
• 英文别名: (4-hydroxyphenyl)(thiophen-2-yl)methanone；2-(4-Hydroxy-benzoyl)-thiophen；4-hydroxyphenyl thien-2-yl ketone；2-(4-hydroxybenzoyl)thiophene；(4-Hydroxy-phenyl)-[2]thienyl-keton；2-thienyl-(4-hydroxy-phenyl)ketone；(4-hydroxyphenyl)-thiophen-2-ylmethanone
• CAS: 38281-73-1
• 化学式: C₁₁H₈O₂S
• 分子量: 204.249
• InChiKey: BVLDPAXUXIUXKB-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  385.2±22.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxyphenyl 2-thienyl ketone 在 氢氧化钾 作用下， 生成 (3-allyl-4-hydroxy-phenyl)-[2]thienyl ketone
  参考文献：
  名称：

  Buu-Hoi et al., Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1083,1103

  摘要：

  DOI：
• 作为产物：
  描述：

  4-acetoxybenzoyl chloride 在 sodium hydroxide 、 四氯化锡 、 苯 作用下， 生成 4-hydroxyphenyl 2-thienyl ketone
  参考文献：
  名称：

  Royer; Demerseman, Bulletin de la Societe Chimique de France, 1959, p. 1682,1685

  摘要：

  DOI：

文献信息

• Non-peptidic inhibitors of human neutrophil elastase: The design and synthesis of sulfonanilide-containing inhibitors
  作者：Katsuhiro Imaki、Takanori Okada、Yoshisuke Nakayama、Yuuki Nagao、Kaoru Kobayashi、Yasuhiro Sakai、Tetsuya Mohri、Takaaki Amino、Hisao Nakai、Masanori Kawamura

  DOI：10.1016/s0968-0896(96)00216-7

  日期：1996.12

  A novel series of pivaloyloxy benzene derivatives has been identified as potent and selective human neutrophil elastase (HNE) inhibitors. Convergent syntheses were developed in order to identify the inhibitors which are intravenously effective in an animal model. A compound of particular interest is the sulfonanilide-containing analogues. Structure-activity relationships are discussed. Structural requirements

  已经鉴定出一系列新的新戊酰氧基苯衍生物作为有效的和选择性的人中性粒细胞弹性蛋白酶（HNE）抑制剂。为了确定在动物模型中静脉内有效的抑制剂，开发了收敛合成法。特别感兴趣的化合物是含磺酰苯胺的类似物。讨论了构效关系。还讨论了代谢稳定的结构要求。
• 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。
• How Understanding the Role of an Additive Can Lead to an Improved Synthetic Protocol without an Additive: Organocatalytic Synthesis of Chiral Diarylmethyl Alkynes
  作者：Min Chen、Jianwei Sun

  DOI：10.1002/anie.201706579

  日期：2017.9.18

  common tactic to improve the outcome of organic reactions. Herein, by using an organocatalytic process for the synthesis of chiral diarylmethyl alkynes as a platform, we describe how an additive is involved in the improvement of the process. The evolution of an excellent synthetic protocol has been achieved in three stages, from 1) initially no catalyst turnover, to 2) good conversion and enantioselectivity

  使用添加剂进行有机合成已成为改善有机反应结果的常用策略。在本文中，通过使用有机催化方法合成手性二芳基甲基炔烃为平台，我们描述了添加剂如何参与改进方法。从三个方面实现了出色的合成方案的发展：从1）最初没有催化剂周转，到2）具有优良添加剂的良好转化率和对映选择性，以及最终3）在没有添加剂的情况下甚至具有更高的效率和选择性。这项研究是一个重要而罕见的证明，即了解添加剂的作用可能会有益于消除添加剂的需求。
• Polymer-supported syntheses of thiophene-containing compounds using a new type of traceless linker
  作者：Abderrazak Ben-Haida、Philip Hodge

  DOI：10.1039/c2ob06714e

  日期：——

  A new type of traceless linker is described for use in polymer-supported (PS) syntheses of thiophene-containing compounds. It is based on the cleavage of PS aryl 2-thienyl ketones by a mixture of potassium t-butoxide and water (typical mol ratio 10 : 3) in an ethereal solvent. Cleavage occurs to give the soluble thiophene-containing product. The method is used to prepare a range of eight thiophene-containing compounds including a terthiophene and a dialkylquaterthiophene. PS unsymmetrical diaryl ketones incorporating, for example, ortho-methoxyphenyl or pyrrole moieties could also serve as traceless linkers.

  描述了一种新型的无痕连接剂，适用于聚合物支持（PS）硫烯类化合物的合成。该连接剂基于在醚溶剂中，使用混合的叔丁氧钾和水（典型摩尔比为10:3）切割PS芳基2-噻吩基酮的反应。切割后产生可溶性的含硫烯产品。该方法用于合成包括三噻吩和双烷基四噻吩在内的八种含硫烯化合物。PS不对称二芳基酮，比如包含邻甲氧基苯基或吡咯基部分的化合物，也可以作为无痕连接剂。
• Hydantoin derivatives
  申请人：Nippon Zoki Pharmaceutical Co., Ltd.

  公开号：US04281009A1

  公开（公告）日：1981-07-28

  New hydantoin derivatives, a process for the preparation thereof and pharmaceutical compositions containing the derivatives as active ingredients, particularly remedies for treatment of diseases caused by stress.

  新的咪唑啉衍生物，其制备方法以及含有这些衍生物作为活性成分的药物组合物，特别是用于治疗由压力引起的疾病的药物。