(2-methylphenyl)-(thiophen-2-yl)methanone | 6933-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methylphenyl)-(thiophen-2-yl)methanone
• 英文别名: (2-thienyl)-(2-methylphenyl)-methanone；(thiophen-2-yl)(o-tolyl)methanone；thiophen-2-yl(o-tolyl)methanone；thiophen-2-yl-o-tolylmethanone；2-(2-methylbenzoyl)thiophene；2-thienyl-2-tolyl ketone；(2-methylphenyl)-thiophen-2-ylmethanone
• CAS: 6933-35-3
• 化学式: C₁₂H₁₀OS
• 分子量: 202.277
• InChiKey: GNSXNNHYZFXSJA-UHFFFAOYSA-N

物化性质

• 沸点：
  180 °C(Press: 18 Torr)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  (2-methylphenyl)-(thiophen-2-yl)methanone 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到(2-methylphenyl)-(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：

  邻甲基苯甲酰氯 在 tris(dibenzylideneacetone)dipalladium (0) 三(2-呋喃基)膦 、 二苯基磷酸亚铜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 生成 (2-methylphenyl)-(thiophen-2-yl)methanone
  参考文献：
  名称：

  在中性条件下合成酮。二苯基次膦酸铜（I）介导的钯催化的硫醇酯和有机锡的偶联反应。

  摘要：

  [反应：见正文]描述了一种通用的酮合成方法。该反应依赖于在中性反应条件下钯催化的，二苯基次膦酸铜铜介导的硫醇酯与有机锡的偶联。该反应补充了先前描述的硫醇酯与硼酸的偶联，该偶联使用了双亲硫基-亲液活化方法。

  DOI：

  10.1021/ol034962x

文献信息

• Sterically Hindered Benzophenones via Rhodium-Catalyzed Oxidative Arylation of Aldehydes
  作者：Olivier Chuzel、Alexander Roesch、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/jo801460w

  日期：2008.10.3

  Efficient cross-coupling, allowing a straightforward access to congested benzophenones, between aromatic aldehydes and potassium aryltrifluoroborates, is described in the presence of a rhodium/tri-tert-butylphosphane catalyst system and acetone as cosolvent. The use of the stable phosphonium salts of tri-tert-butylphosphane prevented the use of highly oxidizable tri-tert-butylphosphane and allowed

  在铑/三叔丁基膦烷催化剂体系和丙酮作为助溶剂的存在下，描述了有效的交叉偶联，使芳族醛和芳基三氟硼酸钾之间可以直接进入拥挤的二苯甲酮。三叔丁基膦的稳定phospho盐的使用阻止了高度可氧化的三叔丁基膦的使用，并允许用铑小心地控制化学计量。
• A Simple, Efficient, and Recyclable Phosphine-Free Catalytic System for Carbonylative Suzuki Coupling Reaction of Aryl and Heteroaryl Iodides
  作者：Bhalchandra Bhanage、Ziyauddin Qureshi、Krishna Deshmukh、Pawan Tambade

  DOI：10.1055/s-0030-1258349

  日期：2011.1

  The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole

  描述了使用聚合物负载的钯-N-杂环卡宾配合物（PS-Pd-NHC）作为有效的多相可循环催化剂，芳基硼酸与芳基和杂芳基碘化物进行羰基化Suzuki偶联反应。发现开发的催化体系对于芳基，杂芳基和双环杂芳基碘化物（5-碘吲哚和3-碘喹啉）与各种芳基硼酸衍生物的羰基化偶联反应有效，从而提供了所需产品的良好或优异的收率。由于催化剂的易于处理和简单的后处理程序，并且对环境有益且催化剂有效地可回收，该方案是有利的。 联芳基酮-硼-多相催化-钯-铃木羰基化
• One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling
  作者：Hongxiang Wu、Baiping Xu、Yue Li、Fengying Hong、Dezhao Zhu、Junsheng Jian、Xiaoer Pu、Zhuo Zeng

  DOI：10.1021/acs.joc.5b02667

  日期：2016.4.1

  A palladium-catalyzed one-pot procedure for the synthesis of aryl ketones has been developed. Triazine esters when coupled with aryl boronic acids provided aryl ketones in moderate to excellent yields (up to 95%) in the presence of 1 mol % Pd(PPh3)2Cl2 for 30 min.

  已经开发了钯催化的一锅法合成芳基酮。三嗪酸酯与芳基硼酸偶联时，在1 mol％Pd（PPh 3）2 Cl 2存在下30分钟，以中等至极好的收率（高达95％）提供芳基酮。
• Pd/C: An Efficient, Heterogeneous and Reusable Catalyst for Phosphane-Free Carbonylative Suzuki Coupling Reactions of Aryl and Heteroaryl Iodides
  作者：Mayur V. Khedkar、Pawan J. Tambade、Ziyauddin S. Qureshi、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201001134

  日期：2010.12

  The carbonylative Suzuki coupling reaction of aryl boronic acid with different aryl and heteroaryl iodides was carried out to synthesize various unsymmetrical biaryl ketones by using Pd/C as an efficient, heterogeneous and reusable catalyst. The catalyst exhibits remarkable activity, and its reusability was tested up to four consecutive cycles. The reaction is applicable for various aryl and heteroaryl

  以Pd/C为高效、多相和可重复使用的催化剂，芳基硼酸与不同芳基和杂芳基碘化物发生羰基化Suzuki偶联反应合成各种不对称联芳基酮。该催化剂表现出显着的活性，其可重复使用性经过连续四个循环的测试。该反应适用于具有不同空间和电子性质的各种芳基和杂芳基碘化物。它提供了良好到极好的所需产品的产率。所开发的协议在易于处理催化剂和简单的后处理程序方面是有利的；它也是一种环保工艺，具有有效的催化剂可回收性。
• 2-(Trifluoromethylsulfonyloxy)pyridine as a Reagent for the Ketone Synthesis from Carboxylic Acids and Aromatic Hydrocarbons
  作者：Takashi Keumi、Kiichiro Yoshimura、Masakazu Shimada、Hidehiko Kitajima

  DOI：10.1246/bcsj.61.455

  日期：1988.2

  A new reagent 2-(trifluoromethylsulfonyloxy)pyridine (TFOP) was prepared by the reaction of sodium salt of 2-pyridinol with trifluoromethylsulfonyl chloride in dioxane. The compound TFOP in trifluoroacetic acid has been found to intermolecularly dehydrate from benzoic acid and aromatic hydrocarbons to give the corresponding benzophenones in high yield. It was further elucidated, in the reaction of

  通过2-吡啶醇的钠盐与三氟甲基磺酰氯在二恶烷中反应制备新试剂2-(三氟甲基磺酰氧基)吡啶(TFOP)。已发现三氟乙酸中的化合物 TFOP 从苯甲酸和芳烃中分子间脱水，以高产率得到相应的二苯甲酮。进一步阐明，在芴反应中，多种羧酸可用作与 TFOP/TFA 系统结合的芳族酮合成的酰基前体。这种酰化方法已被用于合成 2-酰基噻吩，通过使用氯化铝作为催化剂的经典 Friedel-Crafts 反应很难以令人满意的收率制备。