2-benzoyl-5-acetylthiophene | 5912-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-5-acetylthiophene
• 英文别名: 1-(5-Benzoylthiophen-2-yl)ethanone
• CAS: 5912-44-7
• 化学式: C₁₃H₁₀O₂S
• 分子量: 230.287
• InChiKey: AOSMQOCUPQWEQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-benzoyl-5-acetylthiophene 在 Raney Nickel 作用下， 生成 1-苯基庚烷-1,6-二酮
  参考文献：
  名称：

  AlCl₃-Mediated Aldol Cyclocondensation of 1,6- and 1,7-Diones to Cyclopentene and Cyclohexene Derivatives

  摘要：

  Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,omega-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)(3), and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.

  DOI：

  10.1021/jo5006137
• 作为产物：
  描述：

  苯甲酰氯 在 4-二甲氨基吡啶 、 硼酸 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-benzoyl-5-acetylthiophene
  参考文献：
  名称：

  碳氮键裂解钯催化的Suzuki-Miyaura酰胺偶联：酰胺N-C键活化的一般策略†

  摘要：

  据报道，第一个钯催化的Suzuki-Miyaura酰胺与硼酸的交叉偶联通过空间控制的NC键活化来合成酮。该转化的特点是使用稳定的市售试剂和催化剂可简化操作，并具有广泛的底物范围，包括在两个偶合配偶体，位阻，杂环，卤化物，酯和酮上均具有供电子和吸电子基团的底物。范围和局限性在> 60种功能化的酮的合成中给出。机理研究为交叉偶联的催化循环提供了见识，其中包括将Pd插入酰胺N-C键的第一个实验证据。克级交叉耦合和室温下的交叉耦合展示了合成实用程序。最重要的是，通过酰基金属中间体。概述了激活酰胺键以使金属插入到N–C酰胺键中的统一策略（方案1）。

  DOI：

  10.1039/c6ob00084c

文献信息

• Direct Dehydrogenative Access to Unsymmetrical Phenones
  作者：Congjun Yu、Raolin Huang、Frederic W. Patureau

  DOI：10.1002/anie.202201142

  日期：2022.5.9

  The Friedel–Crafts reaction is an emblematic method for constructing C−C bonds at aromatic positions. Rendering this reaction dehydrogenative on a broad scope of substrates under simple reaction conditions constitutes an important milestone for synthetic chemistry.

  弗里德尔-克来福特反应是在芳香位置构建 C−C 键的标志性方法。在简单的反应条件下使该反应在广泛的底物上发生脱氢，是合成化学的一个重要里程碑。
• Photochemistry of Tiaprofenic Acid, a Nonsteroidal Anti-inflammatory Drug with Phototoxic Side Effects
  作者：Francisco Bosca、Miguel A. Miranda、Franklin Vargas

  DOI：10.1002/jps.2600810215

  日期：1992.2

  The phototoxic nonsteroidal anti-inflammatory drug tiaprofenic acid (1) is photolabile under aerobic conditions. Irradiation of a methanol solution of 1 under oxygen produces the photoproducts 2, 3, 4, and 5, and also produces a singlet oxygen as evidenced by trapping with 2,5-dimethylfuran.

  在有氧条件下，光毒性非甾体类抗炎药噻洛芬酸（1）对光不稳定。在氧气下照射1的甲醇溶液会产生光产物2、3、4和5，并且还会产生单线态氧，这可以通过用2,5-二甲基呋喃捕集来证明。
• Mechanism of Lipid Peroxidation Photosensitized by Tiaprofenic Acid: Product Studies Using Linoleic Acid and 1,4-Cyclohexadienes as Model Substrates¶
  作者：Abdelouahid Samadi、Luis A. Martínez、Miguel A. Miranda、Isabel M. Morera

  DOI：10.1562/0031-8655(2001)073<0359:molppb>2.0.co;2

  日期：——

  A careful study of the linoleic acid hydroperoxide (LOOH) profile obtained upon peroxidation of linoleic acid (LA) photosensitized by tiaprofenic acid (TPA) and analogous ketones has been undertaken to distinguish between type-I and type-II photoperoxidation mechanisms. 1,4-Cyclohexadiene and 1,2-dimethylcyclohexa-2,5 -dienecarboxylic acid (CHDCA) have also been used as models for LA since they also have double allylic systems, Co-irradiation of LA with TPA and decarboxytiaprofenic acid (DTPA) in acetonitrile and micellar media produced significant amounts of conjugated dienic LOOH, The cis,trans to trans,trans ratio depended on the irradiation time; thus, this parameter is an ambiguous tool for mechanistic assignment. An interesting finding was the decrease of the LOOH level after long irradiation times in mixtures photooxidized by DTPA, which is attributed to quenching of the DTPA triplet by the generated dienic LOOH, High-performance liquid chromatography analyses confirmed that the main pathway operating in photodynamic lipid peroxidation sensitized by (D)TPA is a type-I mechanism. However, product studies using CHDCA have clearly shown that a type-II mechanism is also operating and might contribute to the overall photooxidation process in a significant way.
• US4266067A
  申请人：——

  公开号：US4266067A

  公开（公告）日：1981-05-05
• Palladium-catalyzed Suzuki–Miyaura coupling of amides by carbon–nitrogen cleavage: general strategy for amide N–C bond activation
  作者：Guangrong Meng、Michal Szostak

  DOI：10.1039/c6ob00084c

  日期：——

  limitations are presented in the synthesis of >60 functionalized ketones. Mechanistic studies provide insight into the catalytic cycle of the cross-coupling, including the first experimental evidence for Pd insertion into the amide N–C bond. The synthetic utility is showcased by a gram-scale cross-coupling and cross-coupling at room temperature. Most importantly, this process provides a blueprint for the

  据报道，第一个钯催化的Suzuki-Miyaura酰胺与硼酸的交叉偶联通过空间控制的NC键活化来合成酮。该转化的特点是使用稳定的市售试剂和催化剂可简化操作，并具有广泛的底物范围，包括在两个偶合配偶体，位阻，杂环，卤化物，酯和酮上均具有供电子和吸电子基团的底物。范围和局限性在> 60种功能化的酮的合成中给出。机理研究为交叉偶联的催化循环提供了见识，其中包括将Pd插入酰胺N-C键的第一个实验证据。克级交叉耦合和室温下的交叉耦合展示了合成实用程序。最重要的是，通过酰基金属中间体。概述了激活酰胺键以使金属插入到N–C酰胺键中的统一策略（方案1）。