3-benzyl-1-cyanonaphthalene | 98689-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyl-1-cyanonaphthalene
• 英文别名: 3-Benzylnaphthalene-1-carbonitrile
• CAS: 98689-34-0
• 化学式: C₁₈H₁₃N
• 分子量: 243.308
• InChiKey: HEQQNPYKVVUXKS-UHFFFAOYSA-N

物化性质

• 沸点：
  422.4±14.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 1.67h， 生成 3-benzyl-1-cyanonaphthalene
  参考文献：
  名称：

  SET Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects

  摘要：

  The electron transfer induced photochemical reactions of 1,4-naphthalenedicarbonitrile (NDN) with toluene (1a), diphenylmethane (1b), p-methoxytoluene (1c), and benzyltrimethylsilane (1d) in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN were examined. The results were compared with those of reactions occurring in neat MeCN. Under the former conditions, the cation radical derived from 1a undergoes deprotonation after diffusion from (rather than within) the geminate ion pair (as in MeCN). The formed benzyl radical abstracts a hydrogen from MeOH leading to hydroxymethylation of NDN competitively with its benzylation. Under basic conditions MeO(-) adds to 1a(+.) yielding 1c. The reaction of 1b in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN is similar to that of 1a. However, in the reaction of 1c under these conditions, the arene cation radical undergoes deprotonation out of cage. Finally, desilylation of the cation radical from 1d is a fast process occurring from the geminate pair in all the media explored.

  DOI：

  10.1021/jo00083a025

文献信息

• Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
  作者：Tyler W. Reidl、Jeffrey S. Bandar

  DOI：10.1021/jacs.1c05764

  日期：2021.8.11

  Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily

  路易斯碱性盐促进苄基三甲基硅烷与（杂）芳基腈、砜和氯化物的偶联，作为制备 1,1-二芳基烷烃的新途径。该方法将交叉耦合的底物模块化和选择性特征与碱基促进协议的实用性结合起来。此外，路易斯碱策略能够对现有方法进行补充，采用稳定且易于制备的有机硅烷，并在酸性官能团存在下实现选择性芳基化。该方法的实用性通过药物类似物的合成及其在多组分反应中的应用得到证明。
• Photoarylmethylation of 1,4-Dicyanonaphthalene by Use of Group 14 Organometallic Compounds
  作者：Kazuhiko Mizuno、Kiyotaro Terasaka、Masahiro Yasueda、Yoshio Otsuji

  DOI：10.1246/cl.1988.145

  日期：1988.1.5

  germane, and stannane in polar solvents gave the arylmethylated products of DCN in high yields. The fluorescence of DCN was efficiently quenched both in polar and nonpolar solvents by these group 14 organometallic compounds. In cyclohexane, the emission from the exciplex between DCN and arylmethylsilanes was observed. The mechanistic features of the photoreaction are described.

  1,4-二氰基萘 (DCN) 与芳甲基硅烷、锗烷和锡烷在极性溶剂中的光反应以高产率得到了 DCN 的芳甲基化产物。DCN 的荧光在极性和非极性溶剂中都被这些第 14 族有机金属化合物有效淬灭。在环己烷中，观察到 DCN 和芳甲基硅烷之间的激基复合物的发射。描述了光反应的机械特征。
• 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...
• LAN, J. Y.;SCHUSTER, G. B., J. AMER. CHEM. SOC., 1985, 107, N 23, 6710-6711
  作者：LAN, J. Y.、SCHUSTER, G. B.

  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：——