3-<1-²H>ethylbenzophenone

• 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-<1-²H>ethylbenzophenone
• 英文别名: decarboxy-<2-2H>-ketoprofen；3-ethylphenyl(phenyl)methanone；decarboxy-[2-2H]-ketoprofen；[3-(1-Deuterioethyl)phenyl]-phenylmethanone
• 化学式: C₁₅H₁₄O
• 分子量: 211.268
• InChiKey: FVSYHKJWZIKKDM-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  酮基布洛芬 在 2,4,6-三甲基吡啶 、 2,4,6-Triisopropylthiophenol 、 重水 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到3-<1-²H>ethylbenzophenone
  参考文献：
  名称：

  A highly selective decarboxylative deuteration of carboxylic acids

  摘要：

  一种可扩展、实用且通用的精确脂肪族羧酸氘代反应方法已经开发出来，通过光氧化还原和氢原子转移催化的协同作用。利用循环反应器实现了制备规模的氘代反应。

  DOI：

  10.1039/d1sc00528f

文献信息

• Ketoprofen as a photoinitiator for anionic polymerization
  作者：Yu-Hsuan Wang、Peter Wan

  DOI：10.1039/c4pp00454j

  日期：2015.6

  efficient photodecarboxylation of Ketoprofen (1) and the related derivatives 3 and 4 that generate the corresponding carbanion intermediates is presented. Carbanion intermediates are confirmed by deuterium incorporation in the trapped Michael adducts and by spectroscopic detection using laser flash photolysis (LFP). This novel anionic initiating system features excitation in the near UV and visible regions

  提出了一种新的光引发体系，用于丙烯酸酯的阴离子聚合，它基于酮洛芬（1）以及产生相应碳负离子中间体的相关衍生物3和4的有效光脱羧作用。通过在捕获的迈克尔加合物中掺入氘和通过使用激光闪光光解（LFP）的光谱检测来确认碳负离子中间体。这种新颖的阴离子引发系统具有在紫外线附近和可见光区域的激发，光控活性聚合的潜在特性以及由光激发产生的无金属光引发剂，这与典型的阴离子聚合不同，后者是由热量和强碱金属碱引发的。
• 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.
• A general procedure for isotopic (deuterium) labelling of non-steroidal antiinflammatory 2-arylpropionic acids
  作者：José V. Castell、Luis A. Martínez、Miguel A. Miranda、Pilar Tárrega

  DOI：10.1002/jlcr.2580340113

  日期：1994.1

  Alkaline treatment of nonsteroidal antiinflammatory 2-arylpropionic acids in deuterium oxide led in all cases to isotopic exchange of the proton located at the α-position of the side chain. Monodeuteration was observed in the case of carprofen, ibuprofen, ketoprofen, fenoprofen, flurbiprofen and naproxen. Additional exchange of one or two protons of the heterocyclic ring occurred in indoprofen, suprofen and tiaprofenic acid. The isotopic labelling survived under the conditions required to perform in vitro photoallergic studies (photolysis in non-deuterated aqueous media).
• A highly selective decarboxylative deuteration of carboxylic acids
  作者：Nian Li、Yunyun Ning、Xiaopeng Wu、Jin Xie、Weipeng Li、Chengjian Zhu

  DOI：10.1039/d1sc00528f

  日期：——

  A scalable, practical and general method for precise deuteration of aliphatic carboxylic acids via synergistic photoredox and HAT catalysis has been developed. The use of recirculation reactor achieved the preparative scale deuteration.

  一种可扩展、实用且通用的精确脂肪族羧酸氘代反应方法已经开发出来，通过光氧化还原和氢原子转移催化的协同作用。利用循环反应器实现了制备规模的氘代反应。