3-(1-hydroperoxyethyl)benzophenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-hydroperoxyethyl)benzophenone
• 英文别名: 1-(3-Benzoylphenyl)ethane-1-peroxol；[3-(1-hydroperoxyethyl)phenyl]-phenylmethanone
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: CHAQYOCADYYFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  酮基布洛芬 在 cerium(III) chloride 、 sodium acetate 作用下， 以 乙腈 为溶剂， 以99 %的产率得到3-(1-hydroperoxyethyl)benzophenone
  参考文献：
  名称：

  羧酸的化学选择性脱羧氧化以获取酮、醛和过氧化物

  摘要：

  此处报道的是一种使用 Ce(III) 催化剂和 O 2作为氧化剂的羧酸化学选择性脱羧氧化的光催化策略。通过简单地改变所用的碱，我们证明反应的选择性可以引导到有利于氢过氧化物或羰基化合物，每一类产品都以良好到极好的收率和高选择性获得。值得注意的是，有价值的酮、醛和过氧化物是直接从容易获得的羧酸中生产出来的，无需额外的步骤。

  DOI：

  10.1021/acs.orglett.3c00649

文献信息

• Topical stabilized formulations containing ketoprofen
  申请人：BERLIN-CHEMIE AG

  公开号：EP1488787A1

  公开（公告）日：2004-12-22

  The invention concerns topical pharmaceutical formulations containing ketoprofen or its S(+) isomer dexketoprofen together with an UV adsorber and an antioxidant.

  本发明涉及含有酮洛芬或其 S（+）异构体右酮洛芬以及紫外线吸附剂和抗氧化剂的外用药物制剂。
• PHOTOCHEMICAL AND PHOTOBIOLOGICAL PROPERTIES OF KETOPROFEN ASSOCIATED WITH THE BENZOPHENONE CHROMOPHORE
  作者：Francisco Boscá、Miguel A. Miranda、Germano Carganico、David Mauleon

  DOI：10.1111/j.1751-1097.1994.tb05073.x

  日期：1994.8

  Abstract Irradiation of ketoprofen in neutral aqueous medium gave rise to 3‐ethylbenzophenone as the major photoproduct. Its formation is justified via protonation of a benzylic carbanion or hydrogen abstraction by a benzylic radical. Minor amounts of eight additional compounds were isolated. Four of them are derived from the benzylic radical: 3‐(1‐hydroperoxyethyl)benzophenone, 3‐(1‐hydroxyethyl)benzophenone, 3‐acetylbenzophenone and 2,3‐bis‐(3‐benzoylphenyl)butane. The other four products involve initial hydrogen abstraction by the excited benzophenone chromophore of ketoprofen: 1,2‐bis‐(3‐ethylphenyl)‐1,2‐diphenyl‐1,2‐ethanediol, 2‐(3‐benzoylphenyl)‐1‐(3‐ethylphenyl)‐1 ‐phenylpropan‐1 ‐01,α ‐(3‐ethylphenyl)phenylmethanol, 1,2‐bis‐[3‐(2‐hydroxycarbonylethyl)phenyl]‐1,2‐di‐phenyl‐1,2‐ethanediol. The latter process was found to mediate the photoperoxidation of linoleic acid through a type I mechanism, as evidenced by the inhibition produced by the radical scavengers butylated hydroxyanisole and reduced glutathione. The major photoproduct, which contains the benzophenone moiety but lacks the propionic acid side chain, also photosensitized linoleic acid peroxidation. Because lipid peroxidation is indicative of cell membrane lysis, the above findings are highly relevant to explain the photobiological properties of ketoprofen.
• EP1613300A2
  申请人：——

  公开号：EP1613300A2

  公开（公告）日：2006-01-11
• PHOTOSTABILIZED TOPICAL FORMULATIONS OF KETOPROFEN CONTAINING TWO UV FILTERS
  申请人：BERLIN-CHEMIE AG

  公开号：EP1613300B1

  公开（公告）日：2008-12-10
• [EN] STABILIZED TOPICAL FORMULATIONS CONTAINING KETOPROFEN<br/>[FR] FORMULATIONS TOPIQUES STABILISEES CONTENANT DU KETOPROFENE
  申请人：BERLIN CHEMIE AG

  公开号：WO2004082580A2

  公开（公告）日：2004-09-30

  The invention relates to topical pharmaceutical formulations containing ketoprofen or its S(+) isomer dexketoprofen or mixtures of the two isomers, together with two UV filters, preferably octyl methoxy cinnamate and phenyl benzimidazol sulphonic acid, and an antioxidant, preferably butyl hydroxy toluene (BHT). The formulations enable a photostability of the active principle, have no, or very low, irritant effect on the skin, are well tolerated, and present an adequate penetration through the skin.