4-乙酰基二苯甲酮乙烯缩醛 | 76509-33-6

• 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: 4-乙酰基二苯甲酮乙烯缩醛
• 英文名称: 4-acetylbenzophenone ethylene acetal
• 英文别名: 1-[4-(2-phenyl-1,3-dioxolan-2-yl)phenyl]ethanone
• CAS: 76509-33-6
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: SSSJLQDONBDJOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-乙酰基二苯甲酮乙烯缩醛 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 二乙二醇 为溶剂， 反应 46.0h， 生成 4-<3-(4-(N,N-dimethylamino)phenyl)propyl>benzophenone
  参考文献：
  名称：

  Exciplex emissions of intra- and intermolecular benzophenone and N,N-dimethylaniline systems

  摘要：

  DOI：

  10.1021/ja00393a023
• 作为产物：
  描述：

  4-氰基苯甲酮 在 氯化铵 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 4-乙酰基二苯甲酮乙烯缩醛
  参考文献：
  名称：

  Exciplex emissions of intra- and intermolecular benzophenone and N,N-dimethylaniline systems

  摘要：

  DOI：

  10.1021/ja00393a023

文献信息

• Laser flash photolysis studies on intramolecular hydrogen atom transfer of [(hydroxynaphthyl)propyl]benzophenone and intramolecular proton-induced electron transfer of [(methoxynaphthyl)propyl]benzophenone via triplet exciplexes
  作者：Tetsuhiro Sekiguchi、Minoru Yamaji、Hitoshi Tatemitsu、Yoshiteru Sakata、Haruo Shizuka

  DOI：10.1021/j100129a015

  日期：1993.7

  Laser photolysis studies at 355 nm have been carried out on the intramolecular hydrogen atom transfer (intra-HT) reaction of [(hydroxynaphthyl)propyl]benzophenone, BP-(CH2)3-ROH, and the proton-induced intramolecular ionization (intra-p-ion) reaction of [(methoxynaphthyl)propyl]benzophenone, BP-(CH2)3-ROMe, in acetonitrile-water (4:1 v/v) at 295 K. After 355-nm laser pulsing to BP-(CH2)3-ROH and BP-(CH2)3-ROMe, the intramolecular triplet energy transfer (intra-ET) reactions from the triplet moiety (3BP*) to the naphthol (ROH) and methoxynaphthalene (ROMe) moieties occur to yield BP-(CH2)3-3ROH* and BP-(CH2)3-3ROMe* on a nanosecond time scale. The former triplet molecule (BP-(CH2)3-3ROH*) undergoes intramolecular hydrogen atom transfer (intra-HT) with an efficiency (phi(HT)) of unity to yield a biradical molecule with benzophenone ketyl radical (>COH-) and naphthoxy radical (RO') moieties (>COH-(CH2)3-RO.). The rate constant (k(HT)) for intra-HT was determined to be 9.8 x 105 s-1 and independent of [BP-(CH2)3-ROH]. The deuterium isotope effect on intra-HT was examined by using BP-(CH2)3-ROD. The rate constant (k(DT)) for intra-DT was determined to be 5.1 X 10(5) S-1. In the presence of protons, the rate constant of intra-HT is enhanced proportional to the acid concentration though the value of phi(HT) (= 1.0) is independent of the acid concentration. The triplet molecule (BP-(CH2)3-3ROMe*) undergoes ionization only in the presence of protons (intra-p-ion) to yield a biradical molecule with >COH- and methoxynaphthalene cation radical (-ROMe.+) moieties (>COH-(CH2)3-ROMe.+) with efficiencies (phi(el)) of 0.3 for [H2SO4] = 0.005 M and 1.0 for [H2SO4] = 0.5 M in acetonitrile-water (4:1 v/v) at 295 K. The rate constant for intra-p-ion increases with an increase of the acid concentration. The mechanisms for intra-HT and intra-p-ion were interpreted by considering the intramolecular triplet exciplexes, 3(>CO-(CH2)3-ROH)* and 3(>CO-(CH2)3-ROMe)*, and the intramolecular protonated triplet exciplexes, 3(>+COH-(CH2)3-ROH)* and 3(>+COH-(CH2)3-ROMe)*, respectively. On the basis of the mechanism for intra-HT and intra-p-ion of the two chromophores linked with a propyrene chain, the structures of the triplet exciplex and protonated triplet exciplex are suggested to be sandwichlike with weak charge-transfer character.