2-Benzoyl-5-(1-hydroxyethyl)thiophene | 143379-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Benzoyl-5-(1-hydroxyethyl)thiophene
• 英文别名: [5-(1-Hydroxyethyl)thiophen-2-yl](phenyl)methanone；[5-(1-hydroxyethyl)thiophen-2-yl]-phenylmethanone
• CAS: 143379-91-3
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: QZSIULAZQIIMCN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.0±35.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  噻洛芬酸 在 N-溴代丁二酰亚胺(NBS) 、 水 、 silver nitrate 作用下， 以 甲醇 、 四氯化碳 、 丙酮 为溶剂， 反应 24.0h， 生成 2-Benzoyl-5-(1-hydroxyethyl)thiophene
  参考文献：
  名称：

  噻洛芬酸的光化学作用，一种非甾体抗炎药，具有光毒副作用。

  摘要：

  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。

  DOI：

  10.1002/jps.2600810215

文献信息

• 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.
• 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。