(5-chlorothiophen-2-yl)(phenyl)methanone | 56824-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-chlorothiophen-2-yl)(phenyl)methanone
• 英文别名: 2-(5-Chlor)-thienylphenylketon；Methanone, (5-chloro-2-thienyl)phenyl-；(5-chlorothiophen-2-yl)-phenylmethanone
• CAS: 56824-84-1
• 化学式: C₁₁H₇ClOS
• mdl: MFCD01927340
• 分子量: 222.695
• InChiKey: HGDKOUQMGFUNRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-chlorothiophen-2-yl)(phenyl)methanone 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到苯基-(5-氯噻吩-2-基)甲醇
  参考文献：
  名称：

  Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation

  摘要：

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-{alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

  DOI：

  10.1021/jm050273a
• 作为产物：
  描述：

  2-氯噻吩-5-甲酸 在 三氯化铝 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (5-chlorothiophen-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Nouveaux agents anti-fongiques imidazoliques dérivés du benzo[b]thiophene. Partie II

  摘要：

  DOI：

  10.1016/0223-5234(88)90146-8

文献信息

• A Mild and Efficient Synthesis of Aryl Sulfones from Aryl Chlorides and Sulfinic Acid Salts Using Microwave Heating
  作者：Sheng-rong Guo、Yan-qin Yuan

  DOI：10.1055/s-0031-1289541

  日期：2011.11

  The CuCl-catalyzed coupling of aryl chlorides and sulfinic acid salts provides a simple and extremely efficient route to unsymmetrical aryl sulfones in high to excellent yields under microwave irradiation within 3-30 minutes.

  CuCl催化的芳基氯与亚磺酸盐的耦合反应提供了一条简单且极其高效的途径，在微波辐射下仅需3-30分钟即可获得高至极佳产率的非对称芳基砜类化合物。
• Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: an efficient route to aryl ketones
  作者：Lijun Gu、Cheng Jin、Jiyan Liu

  DOI：10.1039/c5gc00644a

  日期：——

  A visible-light promoted transformation of aryl diazonium salts and (hetero)arenes for the synthesis of aryl ketones under base-free and metal-free conditions is described.

  描述了在无碱和无金属条件下芳基重氮盐和（杂）芳烃的可见光促进的转化，用于芳基酮的合成。
• Palladium-Catalyzed Cyanation Reactions of Thiophene Halides
  作者：Thomas Erker、Stephanie Nemec

  DOI：10.1055/s-2003-42490

  日期：——

  The described method provides an efficient cyanation reaction of thiophene halides using tris(dibenzylidene-acetone)di­palladium(0), 1,1′-bis-(diphenylphosphino)ferrocene) and zinc powder as the catalyst system and Zn(CN)2 as the cyanide source. Several thiophenes with various substituents are effectively cyanated under these conditions.

  所描述的方法提供了一种高效的噻吩卤化物氰化反应，使用三（二苯甲基-丙酮）二钯（0）、1,1'-双（苯基膦）铁烯和锌粉作为催化体系，以Zn(CN)2作为氰化源。在这些条件下，几种具有不同取代基的噻吩被有效地氰化。
• Heteroaryl manganese reagents: direct preparation and reactivity studies
  作者：Reuben D. Rieke、YoungSung Suh、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2005.06.092

  日期：2005.8

  Direct preparation of various heteroaryl manganese reagents was performed by using highly active manganese (Mn∗) and heteroaryl halides. The resulting organomanganese reagents were coupled with electrophiles such as aryl halides, vinyl halides, and benzoyl chlorides under mild reaction conditions. The corresponding coupling products were obtained in good yields.

  使用高活性锰（Mn *）和杂芳基卤化物可以直接制备各种杂芳基锰试剂。在温和的反应条件下，将所得的有机锰试剂与亲电试剂（例如芳基卤化物，乙烯基卤化物和苯甲酰氯）偶联。以良好的产率获得了相应的偶联产物。
• A novel class of 5-HT2a receptor antagonists: Aryl aminoguanidines
  作者：Henry U. Bryant、David L. Nelson、Donald Button、Harlan W. Cole、Melvyn B. Baez、Virginia L. Lucaites、David B. Wainscott、Cecilia Whitesitt、Jon Reel、Richard Simon、Gary A. Koppel

  DOI：10.1016/0024-3205(96)00449-3

  日期：1996.9

  is prevented by 5-HT2 antagonists such as ketanserin or mianserin. Here we report the effects of a new class of aminoguanidine 5-HT2 antagonists, with relative selectivity for 5-HT2A receptors which are potent inhibitors of 5-HT-induced paw edema in the rat. Radioligand binding studies with 125I DOI on human 5-HT2A and 5-HT2C receptors and with 3H-5-HT on human 5-HT2B receptors demonstrated that, LY314228

  血清素（5-HT）的局部递送通过增加的液体外渗在软组织中产生快速的水肿反应，而5-HT2拮抗剂（如酮色林或米安色林）阻止了这种现象。在这里，我们报告了新型的氨基胍5-HT2拮抗剂的作用，对5-HT2A受体具有相对选择性，5-HT2A受体是大鼠中5-HT诱导的爪水肿的有效抑制剂。用125 I DOI对人5-HT2A和5-HT2C受体以及对3H-5-HT对人5-HT2B受体的放射性配体结合研究表明，LY314228和LY320954对5-HT2A受体表现出一定的选择性。与其他5-HT2受体亚型的结合相比，LY314228对5-HT2A的亲和力比5-HT2B的亲和力高18.6倍，对5-HT2C的亲和力则高2.6倍。LY320954对5-HT2A位点显示出相似的偏好。两种化合物均能抑制5-HT诱导的大鼠足肿胀，ED50为6.4和4.8 mg / kg（分别针对LY314228和LY320954）。这些研究为5-HT