4-(2-丙烯基)-萘-1-甲腈 | 102359-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-(2-丙烯基)-萘-1-甲腈
• 英文名称: 1-allyl-4-cyanonaphthalene
• 英文别名: 4-Allyl-1-naphthonitrile；4-prop-2-enylnaphthalene-1-carbonitrile
• CAS: 102359-60-4
• 化学式: C₁₄H₁₁N
• 分子量: 193.248
• InChiKey: FRDQAZSHJWHOGG-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  354.2±21.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  萘-1,4-二腈 在 芘 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.5h， 生成 4-(2-丙烯基)-萘-1-甲腈
  参考文献：
  名称：

  1,4-二氰基萘与烯丙基硅烷的光化学反应：通过使用溶剂和加成效应控制反应模式

  摘要：

  研究了溶剂和添加剂对1,4-二氰基萘（1,4-DCN）与烯丙基硅烷（1a–c）的光反应的影响。在NaOMe的存在下，辐照含有1,4-DCN和1a-c的乙腈溶液，可以高收率选择性地提供取代产物1-（2'-烯基）-4-氰基萘（2a-c）。在CH 3 CN-MeOH（4：1）中，在of存在下1,4-DCN与1a–c的光反应选择性地提供了加成产物1-（2'-烯基）-1,4-二氰基-1,2 -二氢萘（3a–c，3c'）高产。CH 3中菲存在下1,4-DCN与1a-c的光反应CN-MeOH（4：1）提供三环化合物3,6-dicyano-4,5-苯并三环-[4.2.1.0 3,8 ] -4-壬烯（4a–c，4c'）和5b（4b），这是通过3a–c和2c'的分子内（3π+2π）光环加成反应产生的。讨论了这些光反应的机理。

  DOI：

  10.1016/s0040-4020(01)81184-4

文献信息

• Regioselective photoallylations of dicyanopolycyclic aromatic compounds via electron transfer
  作者：Kazuhiko Mizuno、Kiyotaro Terasaka、Munehiro Ikeda、Yoshio Otsuji

  DOI：10.1016/s0040-4039(00)98935-4

  日期：——

  Upon irradiation with allyltrimethylsilane, dicyanopolycyclic aromatic compounds undergo two modes of photoallylations, depending on the compounds and the reaction conditions. Both the photoreactions occur in a highly regioselective manner via electron transfer.

  在用烯丙基三甲基硅烷辐照时，取决于化合物和反应条件，二氰基多环芳族化合物经历两种光烯丙基化方式。两种光反应都通过电子转移以高度区域选择性的方式发生。
• Photosubstitution of Dicyanoarenes by Hypervalent Allylsilicon Reagents via Photoinduced Electron Transfer
  作者：Daisuke Matsuoka、Yutaka Nishigaichi

  DOI：10.1246/cl.131132

  日期：2014.4.5

  Photosubstitution of dicyanoarenes with hypervalent allylsilicon reagents in the presence of anthracene efficiently proceeded to afford the allyl-substituted product in moderate to good yields. The efficiency for the present photoreaction was much higher than that for the tetracoordinate allylsilanes, because hypervalent allylsilicon reagents possess lower oxidation potential than the tetracoordinate ones, which resulted in more efficient photoinduced electron-transfer process.

  在蒽的存在下，二氰基烯烃与高价烯丙基硅试剂的光取代反应可以有效地进行，从而得到烯丙基取代的产物，收率为中等到良好。与四配位烯丙基硅烷相比，本光反应的效率要高得多，这是因为高价烯丙基硅试剂的氧化电位比四配位烯丙基硅试剂的氧化电位低，因此光诱导电子转移过程的效率更高。
• 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.
• NAKANISHI, KAZUHISA;MIZUNO, KAZUHIKO;OTSUJI, YOSHIO, J. CHEM. SOC. CHEM. COMMUN.,(1991) N, C. 90-92
  作者：NAKANISHI, KAZUHISA、MIZUNO, KAZUHIKO、OTSUJI, YOSHIO

  DOI：——

  日期：——
• MIZUNO, KAZUHIKO;TERASAKA, KIYOTARO;IKEDA, MUNEHIRO;OTSUJI, YOSHIO, TETRAHEDRON LETT., 1985, 26, N 47, 5819-5822
  作者：MIZUNO, KAZUHIKO、TERASAKA, KIYOTARO、IKEDA, MUNEHIRO、OTSUJI, YOSHIO

  DOI：——

  日期：——