2-(2-苯甲酰基苯基)丙醛 | 84810-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-苯甲酰基苯基)丙醛
• 英文名称: 2-(o-Benzoylphenyl)propanal
• 英文别名: 2-(2-benzoylphenyl)propanal
• CAS: 84810-25-3
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: HCKRYHKGADVPFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-苯甲酰基苯基)丙醛 在 臭氧 、 苯基锂 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 endo-1-methyl-3-phenylindene ozonide
  参考文献：
  名称：

  Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation

  摘要：

  Ozonolyses of 3-methyl- and 3-isopropyl-1-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtained in good yield, the exo isomer being the major one. The ozonolyses of two stereoisomeric keto vinyl ethers, (E)-16 and (Z)-16, demonstrated that the stereochemistry of the derived carbonyl oxide 5c exerts a remarkable influence on the course of the reaction. Particularly interesting is the fact that syn-5c having a proper geometry for the concerted cycloaddition provided ozonide 2c in high yield even in the presence of trifluoroacetophenone. The high degree of similarity in the nature and distribution of the products from the ozonolyses of keto olefin (E)-16 and 1-methyl-3-phenylindene (1c) would be consistent with their respective reactions proceeding predominantly through a common carbonyl oxide intermediate syn-5c.

  DOI：

  10.1021/jo980542n
• 作为产物：
  描述：

  (Z)-[2-(1-methyl-3-methoxy-2-propenyl)phenyl]phenylmethanone 在 臭氧 、 三苯基膦 作用下， 以 乙醚 、 苯 为溶剂， 生成 2-(2-苯甲酰基苯基)丙醛
  参考文献：
  名称：

  Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation

  摘要：

  Ozonolyses of 3-methyl- and 3-isopropyl-1-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtained in good yield, the exo isomer being the major one. The ozonolyses of two stereoisomeric keto vinyl ethers, (E)-16 and (Z)-16, demonstrated that the stereochemistry of the derived carbonyl oxide 5c exerts a remarkable influence on the course of the reaction. Particularly interesting is the fact that syn-5c having a proper geometry for the concerted cycloaddition provided ozonide 2c in high yield even in the presence of trifluoroacetophenone. The high degree of similarity in the nature and distribution of the products from the ozonolyses of keto olefin (E)-16 and 1-methyl-3-phenylindene (1c) would be consistent with their respective reactions proceeding predominantly through a common carbonyl oxide intermediate syn-5c.

  DOI：

  10.1021/jo980542n

文献信息

• ¹⁸O-Tracer Studies of Fe(II)-Induced Decomposition of 1,2,4-Trioxolanes (Ozonides) Derived from Cyclopentenes and Indenes. Inner-Sphere Electron Transfer Reduction of the Peroxide Linkage
  作者：Manabu Abe、Tomoyasu Inakazu、Johichi Munakata、Masatomo Nojima

  DOI：10.1021/ja990807v

  日期：1999.7.1

  Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) 1 and 2 is studied in detail. The inner-sphere electron transfer reduction, which is sensitive to steric effects, is proposed to be a reasonable mechanism for the peroxide decomposition, i.e., the selective generation of one of the two possible Fe(III)-complexed oxy radicals. The fate of the oxy radical species is revealed in detail by using

  详细研究了 Fe(II) 诱导的 1,2,4-三氧戊环（臭氧化物）1 和 2 的分解。对空间效应敏感的球内电子转移还原被认为是过氧化物分解的合理机制，即选择性生成两种可能的 Fe(III) 络合氧自由基之一。通过在 18O 标记的臭氧化物 1a 和 2a 的还原中使用 18O 示踪剂研究详细揭示了氧自由基物种的命运，其中醚氧被 18O 原子（18O，77%）标记，并且还通过还原在 H218O (18O, 10%) 存在下。18O 示踪剂研究的结果与 Fe(III) 络合氧自由基物种的区域选择性生成一致。
• Syntheses, structure analyses, and reactions of 1,3,5-trioxepanes and related compounds
  作者：Kevin J. McCullough、Araki Masuyama、Keith M. Morgan、Masatomo Nojima、Yuji Okada、Syuzo Satake、Shin-ya Takeda

  DOI：10.1039/a802928h

  日期：——

  Acid-catalysed condensations of 1,5- or 1,6-dicarbonyl compounds with ethylene glycol give 1,3,5-trioxepane derivatives as a result of neighbouring participation by the adjacent carbonyl group during the acetalization process. With trimethylene glycol, the related 1,3,5-trioxocanes have also been obtained. Reaction of the 1,3,5-trioxepanes with (a) Grignard reagents gives dialkyl-substituted cyclic

  1，5-或1，6-二羰基化合物与乙二醇的酸催化缩合产生1,3,5-三氧杂环丁烷衍生物，这是由于缩醛化过程中相邻羰基的相邻参与。使用三亚甲基二醇，也已经获得了相关的1,3,5-三氧杂环丁烷。1,3,5-三氧杂环丁烷与（a）格氏试剂反应生成二烷基取代的环状醚，（b）四氯化钛-烯丙基三丁基锡生成二烯丙基取代的环状醚，（c）在三氟甲磺酸三甲基甲硅烷基酯存在下的三乙基硅烷提供了相应的环醚。
• Structure-reactivity relationships in (2-hydroxyethyl)benzophenone photoremovable protecting Groups
  作者：Michael C. Pirrung、Biswajit Gopal Roy、Surendra Gadamsetty

  DOI：10.1016/j.tet.2010.02.087

  日期：2010.4

  A detailed study of substituent effects on the photochemical conversion of esters of (2-hydroxyethyl)benzophenone to the carboxylic acid was performed with the aim of improving on the reactivity of the parent, which was first reported decades ago. Over 20 derivatives were prepared, 10 of which exhibit some level of photochemical reactivity, but none of them is appreciably better than the original.

  为了改善母体的反应性，进行了取代基对（2-羟乙基）二苯甲酮的酯光化学转化为羧酸的影响的详细研究，这是几十年前首次报道的。制备了20多种衍生物，其中10种表现出一定程度的光化学反应性，但没有一个比原始的有明显的改善。该反应对作为致敏剂的噻吨酮或包含碱以促进消除反应均无反应。除全氟苯基类似物外，该溶剂对反应的影响似乎很小，该全氟苯基类似物在己烷中完全不反应，但在甲醇或乙腈中则表现正常。这些被忽略的保护基即使在长波长照射下也可以相当快速地脱保护，仍然可以用于有机合成中。
• McCullough, Kevin J.; Sugimoto, Toshiya; Tanaka, Shogo, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 643 - 652
  作者：McCullough, Kevin J.、Sugimoto, Toshiya、Tanaka, Shogo、Kusabayashi, Shigekazu、Nojima, Masatomo

  DOI：——

  日期：——
• Sugimoto, Toshiya; Nojima, Masatomo; Kusabayashi, Shigekazu, Journal of the American Chemical Society, 1990, vol. 112, # 9, p. 3690 - 3692
  作者：Sugimoto, Toshiya、Nojima, Masatomo、Kusabayashi, Shigekazu、McCullough, Kevin J.

  DOI：——

  日期：——