3,4-dihydro-4-(2-propenyl)naphthalene-1-carbonitrile | 144001-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydro-4-(2-propenyl)naphthalene-1-carbonitrile
• 英文别名: 4-Prop-2-enyl-3,4-dihydronaphthalene-1-carbonitrile
• CAS: 144001-71-8
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: PUWCDLWZYWTRFU-UHFFFAOYSA-N

物化性质

• 沸点：
  333.0±27.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-4-(2-propenyl)naphthalene-1-carbonitrile 以 乙腈 为溶剂， 反应 1.5h， 生成 tetracyclo<6.3.2.0^2,7.0^10,13>trideca-2,4,6-triene-8-carbonitrile
  参考文献：
  名称：

  The photochemical reaction between aromatic nitriles and allylsilane

  摘要：

  The results obtained from the irradiation of aromatic nitriles and allyltrimethylsilane (ATMS) depend on the redox parameters of these molecules and their singlet energies. The reaction between 1-naphthalenecarbonitrile (NN) and ATMS in apolar solvents leads to [2 + 2] cycloaddition at positions 1 and 2 (via the exciplex); in polar solvents, electron transfer becomes a possibility, and loss of the trimethylsilyl cation followed by allylation of NN at positions 2 and 4 is also observed. When naphthalene-1,4-dicarbonitrile (NDN) is used, electron-transfer-initiated allylation (both addition and cyano group substitution) is the main pathway, but in apolar solvents cycloaddition at positions 4a and 5 occurs as a minor pathway. The reaction with benzene-1,2,4,5-tetracarbonitrile (BTN) gives substitution of an allyl for a cyano group as the only process. Finally, with both NDN and BTN and a high ATMS concentration in apolar solvents, the reaction pathway changes to photosensitized [2 + 2] dimerization of ATMS, proposed to occur via a terplex. Rationalizations for the observed reactions (including regiochemistry of addition and cycloaddition and nature of the intermediates) are offered.

  DOI：

  10.1021/jo00049a031
• 作为产物：
  描述：

  烯丙基三甲基硅烷 、 氰基萘 以 乙腈 为溶剂， 反应 7.0h， 以14%的产率得到3,4-dihydro-4-(2-propenyl)naphthalene-1-carbonitrile
  参考文献：
  名称：

  The photochemical reaction between aromatic nitriles and allylsilane

  摘要：

  The results obtained from the irradiation of aromatic nitriles and allyltrimethylsilane (ATMS) depend on the redox parameters of these molecules and their singlet energies. The reaction between 1-naphthalenecarbonitrile (NN) and ATMS in apolar solvents leads to [2 + 2] cycloaddition at positions 1 and 2 (via the exciplex); in polar solvents, electron transfer becomes a possibility, and loss of the trimethylsilyl cation followed by allylation of NN at positions 2 and 4 is also observed. When naphthalene-1,4-dicarbonitrile (NDN) is used, electron-transfer-initiated allylation (both addition and cyano group substitution) is the main pathway, but in apolar solvents cycloaddition at positions 4a and 5 occurs as a minor pathway. The reaction with benzene-1,2,4,5-tetracarbonitrile (BTN) gives substitution of an allyl for a cyano group as the only process. Finally, with both NDN and BTN and a high ATMS concentration in apolar solvents, the reaction pathway changes to photosensitized [2 + 2] dimerization of ATMS, proposed to occur via a terplex. Rationalizations for the observed reactions (including regiochemistry of addition and cycloaddition and nature of the intermediates) are offered.

  DOI：

  10.1021/jo00049a031

文献信息

• The photochemical reaction between aromatic nitriles and allylsilane
  作者：M. Mella、E. Fasani、A. Albini

  DOI：10.1021/jo00049a031

  日期：1992.11

  The results obtained from the irradiation of aromatic nitriles and allyltrimethylsilane (ATMS) depend on the redox parameters of these molecules and their singlet energies. The reaction between 1-naphthalenecarbonitrile (NN) and ATMS in apolar solvents leads to [2 + 2] cycloaddition at positions 1 and 2 (via the exciplex); in polar solvents, electron transfer becomes a possibility, and loss of the trimethylsilyl cation followed by allylation of NN at positions 2 and 4 is also observed. When naphthalene-1,4-dicarbonitrile (NDN) is used, electron-transfer-initiated allylation (both addition and cyano group substitution) is the main pathway, but in apolar solvents cycloaddition at positions 4a and 5 occurs as a minor pathway. The reaction with benzene-1,2,4,5-tetracarbonitrile (BTN) gives substitution of an allyl for a cyano group as the only process. Finally, with both NDN and BTN and a high ATMS concentration in apolar solvents, the reaction pathway changes to photosensitized [2 + 2] dimerization of ATMS, proposed to occur via a terplex. Rationalizations for the observed reactions (including regiochemistry of addition and cycloaddition and nature of the intermediates) are offered.