1-(2-丙烯基)-1,2-二氢萘-1,4-二腈 | 102359-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-丙烯基)-1,2-二氢萘-1,4-二腈
• 英文名称: 1-allyl-1,4-dicyano-1,2-dihydronaphthalene
• 英文别名: 1-allyl-2H-naphthalene-1,4-dicarbonitrile；1-prop-2-enyl-2H-naphthalene-1,4-dicarbonitrile
• CAS: 102359-61-5
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: OOZMSSXXLKAFPX-UHFFFAOYSA-N

物化性质

• 沸点：
  400.8±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-丙烯基)-1,2-二氢萘-1,4-二腈 以 乙腈 为溶剂， 生成 3,6-dicyano-4,5-benzotricyclo<4.2.1.0.^3,8>-4-nonene
  参考文献：
  名称：

  用烯丙基三甲基硅烷的单-和dicyanonaphthalenes光诱导电子转移反应：benzotricyclo [4.2.1.0合成3,8 ]通过还原photoallylation和分子内（2壬烯π 2 π）光环

  摘要：

  通过派热克斯滤光片（> 280 nm）辐照含有1-氰基萘和烯丙基三甲基硅烷（1）的乙腈-甲醇（4：1）溶液，区域选择性地产生3-氰基-4,5-苯并三环[4.2.1.0 3,8] -4-壬烯。2-氰基萘，1-氰基-2-甲基萘，1-氰基-4-甲基萘，1，5-和2，3-二氰基萘与1的光反应也以区域选择性的方式得到了相应的苯并三环化合物。然而，2，3-二取代的1，4-二氰基萘与1的光反应没有得到苯并三环化合物，而只得到了烯丙基取代和还原性烯丙基化产物。这些光反应是通过从1到单氰基和双氰基萘的激发单重态的光诱导电子转移引发的。从得到benzotricyclic化合物前者cyanonaphthalenes还原烯丙基化产物通过分子内（2 π 2 π）进行光环加成，收率良好。基于对单氰基和双氰基萘的自由基阴离子的MO计算结果，讨论了烯丙基化反应中的区域选择性。

  DOI：

  10.1016/0040-4020(95)00326-4
• 作为产物：
  描述：

  萘-1,4-二腈 、 乙腈 生成 1-(2-丙烯基)-1,2-二氢萘-1,4-二腈
  参考文献：
  名称：

  NAKANISHI, KAZUHISA;MIZUNO, KAZUHIKO;OTSUJI, YOSHIO, J. CHEM. SOC. CHEM. COMMUN.,(1991) N, C. 90-92

  摘要：

  DOI：

文献信息

• Photochemical reactions of 1,4-dicyanonaphthalene with allylic silanes: control of reaction modes by use of solvent and additive effects
  作者：Kazuhiko Mizuno、Toshinori Nishiyama、Kiyotaro Terasaka、Masahide Yasuda、Kensuke Shima、Yoshio Otsuji

  DOI：10.1016/s0040-4020(01)81184-4

  日期：——

  Solvent and additive effects on the photoreaction of 1,4-dicyanonaphthalene, (1,4-DCN) with allylic silanes (1a–c) have been investigated. Irradiation of acetonitrile solutions containing 1,4-DCN and 1a–c in the presence of NaOMe selectively afforded the substitution products 1-(2′-alkenyl)-4-cyanonaphthalenes (2a–c) in high yields. The photoreaction of1,4-DCN with 1a–c in the presence of pyrene in

  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。
• 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.
• 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：——