1-cyano-3-(4-methylphenylmethyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyano-3-(4-methylphenylmethyl)naphthalene
• 英文别名: 3-[(4-Methylphenyl)methyl]naphthalene-1-carbonitrile
• 化学式: C₁₉H₁₅N
• 分子量: 257.335
• InChiKey: ZYKMYHOLKIPJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲基苯乙酸 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 1-cyano-3-(4-methylphenylmethyl)naphthalene
  参考文献：
  名称：

  Methylbenzene cation radical .alpha.-fragmentation selectivities revealed in SET-photoadditions of p-xylene derivatives to 1,4-dicyanonaphthalene [SET = single electron transfer]

  摘要：

  SET-promoted photoreactions of selected p-xylene derivatives, including p-xylene (3a), p-phenylenediacetic acid (3b), p-bis[(trimethylsilyl)methyl]benzene (3c), p-[(trim ethylsilyl)methyl]toluene (3d), p-tolylacetic acid (3e), and p-[(trimethylsilyl)methyl]phenylacetic acid (3f), to 1,4-dicyanonaphthalene have been investigated. These processes lead to clean and selective formation of 1:1 adducts whose nature is controlled by alpha-heterolytic fragmentation reactions occurring at benzylic positions of arene cation radicals which serve as key reactive intermediates. The results indicate that the relative rates of cation radical fragmentations of the type ([ArCH2E].+ + B: --> ArCH2.+ BE) depend on the nature of the electrofugal group, E, in the following order: E = SiMe3 > CO2H > H. The experimental basis for these conclusions is discussed.

  DOI：

  10.1021/jo00056a029

文献信息

• Photoinduced Electron-Transfer Reactions of Arylmethyl-Substituted 14 Group Compounds: Photoarylmethylation and Photooxygenation
  作者：Toshiyuki Tamai、Kazuhiko Mizuno、Isao Hashida、Yoshio Otsuji

  DOI：10.1246/bcsj.66.3747

  日期：1993.12

  oxygenation of the arylmethyl organometallic compounds occurred in the photoreaction under oxygen atmosphere. Key intermediates in these reactions in acetonitrile were radical ions which were generated via photoinduced electron transfer from the arylmethyl organometallic compounds to the excited singlet of DCN or DCA. The cleavage of the carbon–metal bond of the radical cations of the arylmethyl compounds

  在各种条件下研究了芳基甲基硅烷、-锗烷和-锡烷与 1,4-二氰基萘 (DCN) 和 9,10-二氰基蒽 (DCA) 的光反应。DCN和DCA的芳甲基化发生在氮气气氛下的光反应中，而芳甲基有机金属化合物的氧化发生在氧气气氛下的光反应中。乙腈中这些反应的关键中间体是自由基离子，它们是通过光诱导电子从芳甲基有机金属化合物转移到 DCN 或 DCA 的激发单线态而产生的。芳甲基化合物自由基阳离子的碳-金属键断裂导致芳甲基自由基的形成。然后自由基与 DCN 和 DCA 的自由基阴离子反应生成芳甲基化化合物或与氧反应生成含氧化合物。光反应的效率受溶剂和添加到反应系统中的材料的影响。在光反应...
• dAlessandro Nicola, Albini Angelo, Mariano Patrick S., J. Org. Chem., 58 (1993) N 4, S 937-942
  作者：dAlessandro Nicola, Albini Angelo, Mariano Patrick S.

  DOI：——

  日期：——
• MIZUNO, KAZUHIKO;TERASAKA, KIYOTARO;YASUEDA, MASAHIRO;OTSUJI, YOSHIO, CHEM. LETT.,(1988) N 1, 145-148
  作者：MIZUNO, KAZUHIKO、TERASAKA, KIYOTARO、YASUEDA, MASAHIRO、OTSUJI, YOSHIO

  DOI：——

  日期：——
• Methylbenzene cation radical .alpha.-fragmentation selectivities revealed in SET-photoadditions of p-xylene derivatives to 1,4-dicyanonaphthalene [SET = single electron transfer]
  作者：Nicola D'Alessandro、Angelo Albini、Patrick S. Mariano

  DOI：10.1021/jo00056a029

  日期：1993.2

  SET-promoted photoreactions of selected p-xylene derivatives, including p-xylene (3a), p-phenylenediacetic acid (3b), p-bis[(trimethylsilyl)methyl]benzene (3c), p-[(trim ethylsilyl)methyl]toluene (3d), p-tolylacetic acid (3e), and p-[(trimethylsilyl)methyl]phenylacetic acid (3f), to 1,4-dicyanonaphthalene have been investigated. These processes lead to clean and selective formation of 1:1 adducts whose nature is controlled by alpha-heterolytic fragmentation reactions occurring at benzylic positions of arene cation radicals which serve as key reactive intermediates. The results indicate that the relative rates of cation radical fragmentations of the type ([ArCH2E].+ + B: --> ArCH2.+ BE) depend on the nature of the electrofugal group, E, in the following order: E = SiMe3 > CO2H > H. The experimental basis for these conclusions is discussed.