1-[(4-benzoylphenoxy)methyl]naphthalene | 190264-57-4

• 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: 1-[(4-benzoylphenoxy)methyl]naphthalene
• 英文别名: Methanone, [4-(1-naphthalenylmethoxy)phenyl]phenyl-；[4-(naphthalen-1-ylmethoxy)phenyl]-phenylmethanone
• CAS: 190264-57-4
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: FUPRTHOFUKVSRV-UHFFFAOYSA-N

物化性质

• 沸点：
  532.9±33.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氯化碳 、 乙醇 、 1-[(4-benzoylphenoxy)methyl]naphthalene 生成 1,2-二(1-萘基)乙烷 、 1-萘甲醇 、 1-(2,2,2-trichloroethyl)naphthalene 、 [4-(Ethoxy-naphthalen-1-yl-methoxy)-phenyl]-phenyl-methanone 、 4-羟基-二苯甲酮
  参考文献：
  名称：

  Multiple-Photon Chemistry in the Laser-Jet:  Photochemistry and Time-Resolved Laser-Flash Spectroscopy of the 1-Naphthylmethyl Radical

  摘要：

  In the laser-jet (LJ) photolysis (lambda(exc) 333, 351, and 364 nm, high intensity) of 1-[(4-benzoylphenoxy)methyl]naphthalene (1), a two-photon process is observed in CCl4 to yield 1-(chloromethyl)naphthalene (3a) as the main product, while the one-photon products of the conventional photolysis (low intensity) are 1,2-di(l-naphthyl)ethane (2), 1,1,1-trichloro-2-(l-naphthyl)ethane (3b), and 1-naphthaldehyde (5). In MeOH or EtOH, however, our results suggest even a three-photon reaction in which 1-naphthylmethyl methyl ether (4c) and 1-naphthylmethyl ethyl ether (4b) are produced in addition to the one-photon product 2. The three-photon mechanism is based on a competition experiment in which ether 1 was irradiated in mixtures of CCl4 and methanol. The ratio of the two high-intensity products ether 4c and 1-(chloromethyl)naphthalene (3a) showed a strong intensity dependence. We propose that the electronically excited 1-naphthylmethyl radical 1-NpCH2.* is photochemically ionized to 1-naphthylmethyl cation 1-NpCH2+ under the high-intensity LJ photolysis conditions and the latter trapped by the respective alcohols to give the 1-naphthylmethyl ethers 4c and 4b. With the help of time-resolved laser flash photolysis (248 nm) of 1-[(4-benzoylphenoxy)methyl]naphthalene (1), it was established that homolysis of the C-O bond to yield 1-naphthylmethyl (1-NpCH2.) and 4-benzoylphenoxy (ArO.) radicals takes place. The authentic 1-NpCH2. and ArO. radicals were generated independently by pulse radiolysis of 1-(bromomethyl)- or 1-(chloromethyl)naphthalene in 2-propanol and of 4-hydroxybenzophenone (6) in water (1% tBuOH); in the latter case, SO4.- was used as oxidant. In the LJ photolysis, the triplet state of the 1-naphthylmethyl moiety is probably further excited to yield the observed products.

  DOI：

  10.1021/jo961699n

文献信息

• Multiple-Photon Chemistry in the Laser-Jet:  Photochemistry and Time-Resolved Laser-Flash Spectroscopy of the 1-Naphthylmethyl Radical
  作者：Waldemar Adam、Katrin Schneider、Steen Steenken

  DOI：10.1021/jo961699n

  日期：1997.5.1

  In the laser-jet (LJ) photolysis (lambda(exc) 333, 351, and 364 nm, high intensity) of 1-[(4-benzoylphenoxy)methyl]naphthalene (1), a two-photon process is observed in CCl4 to yield 1-(chloromethyl)naphthalene (3a) as the main product, while the one-photon products of the conventional photolysis (low intensity) are 1,2-di(l-naphthyl)ethane (2), 1,1,1-trichloro-2-(l-naphthyl)ethane (3b), and 1-naphthaldehyde (5). In MeOH or EtOH, however, our results suggest even a three-photon reaction in which 1-naphthylmethyl methyl ether (4c) and 1-naphthylmethyl ethyl ether (4b) are produced in addition to the one-photon product 2. The three-photon mechanism is based on a competition experiment in which ether 1 was irradiated in mixtures of CCl4 and methanol. The ratio of the two high-intensity products ether 4c and 1-(chloromethyl)naphthalene (3a) showed a strong intensity dependence. We propose that the electronically excited 1-naphthylmethyl radical 1-NpCH2.* is photochemically ionized to 1-naphthylmethyl cation 1-NpCH2+ under the high-intensity LJ photolysis conditions and the latter trapped by the respective alcohols to give the 1-naphthylmethyl ethers 4c and 4b. With the help of time-resolved laser flash photolysis (248 nm) of 1-[(4-benzoylphenoxy)methyl]naphthalene (1), it was established that homolysis of the C-O bond to yield 1-naphthylmethyl (1-NpCH2.) and 4-benzoylphenoxy (ArO.) radicals takes place. The authentic 1-NpCH2. and ArO. radicals were generated independently by pulse radiolysis of 1-(bromomethyl)- or 1-(chloromethyl)naphthalene in 2-propanol and of 4-hydroxybenzophenone (6) in water (1% tBuOH); in the latter case, SO4.- was used as oxidant. In the LJ photolysis, the triplet state of the 1-naphthylmethyl moiety is probably further excited to yield the observed products.