(E)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene | 132884-13-0

• 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: (E)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene
• CAS: 132884-13-0
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: QDXJVDQYXYIDRU-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  甲醇 、 1,2-二氢-1-苯基萘 在 硫酸 作用下， 生成 (Z)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene 、 (E)-1-(3-methoxyprop-1-enyl)-2-benzylbenzene 、 (1S,αS,1R,αR)-1-(α-methoxybenzyl)indan 、 (1S,αS,1R,αR)-1-(α-methoxybenzyl)indan
  参考文献：
  名称：

  Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol

  摘要：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

  DOI：

  10.1021/jo00007a033

文献信息

• Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol
  作者：Jan Woning、Frank A. T. Lijten、Wim H. Laarhoven

  DOI：10.1021/jo00007a033

  日期：1991.3

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.