(2-fluorophenyl)-(thiophen-2-yl)methanone | 6933-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-fluorophenyl)-(thiophen-2-yl)methanone
• 英文别名: 2,2'-Fluorobenzoylthiophene；2-o-fluorobenzoylthiophene；o-fluorophenyl thiophene-2-yl ketone；2-(o-Fluor-benzoyl)-thiophen；Methanone, (2-fluorophenyl)-2-thienyl-；(2-fluorophenyl)-thiophen-2-ylmethanone
• CAS: 6933-30-8
• 化学式: C₁₁H₇FOS
• 分子量: 206.24
• InChiKey: FDZRAVDFCKOWKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (2-fluorophenyl)-(thiophen-2-yl)methanone 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到(2-fluorophenyl)-(thiophen-2-yl)methanol
  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-噻吩甲酰氯 、 2-氟碘苯 在 铜 作用下， 生成 (2-fluorophenyl)-(thiophen-2-yl)methanone
  参考文献：
  名称：

  非常稳定的邻卤代苯基铜试剂

  摘要：

  我们希望报告在室温下通过将氧化活性铜直接氧化成邻氟和邻氯代邻苯二甲生成稳定的邻卤代铜试剂。试剂将在25°C与合适的有机卤化物进行取代反应。

  DOI：

  10.1016/s0040-4039(00)77593-9

文献信息

• Oligothiophene-Linked Bisnaphthopyrans: Sequential and Temperature-Dependent Photochromism
  作者：Weili Zhao、Erick M. Carreira

  DOI：10.1002/chem.200600958

  日期：2007.3.16

  Photochromic bisnaphthopyrans linked with oligothiophenes were synthesized and their photochromic behavior studied. Sequential and temperature-dependent photochromism was observed in the oligothiophene linked bisnaphthopyrans. The kinetics of photo and thermal processes in bisnaphthopyrans in comparison with naphthopyrans were studied. Substituent and linking effects on the photochromic properties

  合成了与寡噻吩连接的光致变色双萘并吡喃并研究了它们的光致变色行为。在寡噻吩连接的双萘并吡喃中观察到顺序和温度相关的光致变色现象。研究了萘并吡喃与萘并吡喃的光和热过程动力学。讨论了取代基和连接效应对光致变色性质的影响。我们证明了两个光致发色团之间的串扰取决于寡噻吩接头的长度。联噻吩接头的存在导致了高着色性和着色的高量子产率。
• Continuous flow synthesis of diaryl ketones by coupling of aryl Grignard reagents with acyl chlorides under mild conditions in the ecofriendly solvent 2-methyltetrahydrofuran
  作者：Chuan-Tao Zhang、Rui Zhu、Zheng Wang、Bing Ma、Adrian Zajac、Marcin Smiglak、Chun-Nian Xia、Steven L. Castle、Wen-Long Wang

  DOI：10.1039/c8ra07447j

  日期：——

  efficient continuous flow sequential synthesis of diaryl ketones was achieved by coupling of aryl Grignard reagents with acyl chlorides in the bio-derived “green” solvent 2-methyltetrahydrofuran (2-MeTHF) under mild reaction conditions (ambient temperature, 1 hour), allowing a safe and on-demand generation of 2-(3-benzoylphenyl)propionitrile with a productivity of 3.16 g hour−1.

  在温和的反应条件（环境温度，1 小时）下，芳基格氏试剂与酰氯在生物衍生的“绿色”溶剂 2-甲基四氢呋喃 (2-MeTHF) 中偶联，实现了二芳基酮的高效连续流动顺序合成，允许2-(3-苯甲酰基苯基)丙腈的安全和按需生产，产率为3.16 g·h -1。
• 一种连续流微反应器合成二苯甲酮衍生物的 方法
  申请人：江南大学

  公开号：CN108409516B

  公开（公告）日：2020-06-09

  本发明属于有机合成技术领域，具体涉及一种利用连续流微反应器制备二苯甲酮衍生物的方法，该方法是以芳基格氏试剂和酰氯为原料，常温下，在微反应器内连续化合成二苯甲酮衍生物，循环利用反应溶剂2‑甲基四氢呋喃，本发明避免了传统傅克反应过度依赖三氯化铝、三氯化铁、二氯化锌等试剂带来的环境污染和反应操作安全性的问题，弥补新型催化工艺存在的催化试剂昂贵、操作条件苛刻等缺陷，高效实现了医药中间体氰基酮洛芬的连续化合成，具有操作便捷性好、反应安全性高、产率高、效率高、反应溶剂可重复使用等特点，是一种绿色环保高效的合成二苯甲酮衍生物的方法。
• Direct Formation of (Haloaryl)copper Nucleophiles from Haloiodobenzenes and Active Copper
  作者：Greg W. Ebert、Deborah R. Pfennig、Scott D. Suchan、Thomas A. Donovan、Emmanuel Aouad、Safa S. Tehrani、James N. Gunnersen、Liming Dong

  DOI：10.1021/jo00113a013

  日期：1995.4

  (o-Halophenyl)-; (m-halophenyl)-, and (p-halophenyl)copper reagents have been formed in moderate to high yields at room temperature from active copper and the corresponding haloiodobenzenes. These reagents have been cross-coupled with a variety of alkyl and acyl halides to produce the respective haloarenes and haloaryl ketones. Remarkably, (o-fluorophenyl)- and (o-chlorophenyl)copper are produced in good yields by this procedure without undergoing elimination to form benzyne making this approach a convenient method for generating o-halophenyl nucleophiles.
• Synthesis and sequential photochromism of thiophene-linked bis-pyrans
  作者：Xiuhong Lu、Qian Dong、Xiaochun Dong、Weili Zhao

  DOI：10.1016/j.tet.2015.04.068

  日期：2015.6

  Novel bis[3H]-naphtho[2,1-b]pyrans 1a-1g and bis[2H]-naphtho[1,2-b]pyrans 2a-2g were prepared efficiently. Such thiophene-linked bispyrans display distinct color change under continuous UV irradiation with up to 110 am of bathochromic shift between the finally generated colored forms and initially generated forms. They also show high colorability, as well as good fatigue-resistance. (C) 2015 Elsevier Ltd. All rights reserved.