(2Z,4E)-2,5-diphenylpenta-2,4-dienenitrile | 79144-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z,4E)-2,5-diphenylpenta-2,4-dienenitrile
• 英文别名: Benzeneacetonitrile, alpha-[3-phenyl-2-propen-1-ylidene]-
• CAS: 79144-43-7
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: MEAXDVRKAWCVJF-UVZCHINQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (2Z,4E)-2,5-diphenylpenta-2,4-dienenitrile 以 solid 为溶剂， 生成 1,3-Diphenyl-2,4-bis-((E)-styryl)-cyclobutane-1,3-dicarbonitrile
  参考文献：
  名称：

  Fluorescence and Photodimerization Studies of Cyano-Substituted Diphenylbutadienes

  摘要：

  Fluorescent emission and photodimerization of crystalline (1E,3E)-1,4-diphenylbutadiene (2, DPB), (IZ,3E)l-cyano-1 ,4-diphenylbutadiene (3, CDPB) and (1Z, 3E)-1-cyano-3-methyl-1,4-diphenplbutadiene (4, CMDPB) have been studied. Although crystals of all the three dienes exhibit red-shifted fluorescence, only CDPB (3) crystals give [2 + 2] photoproduct on photolysis, despite having a rather long center-to-center distance of 5.04 Angstrom between cyano-substituted double bonds. Large differences in the absorption and fluorescence excitation spectra are observed for crystalline dienes. For example, absorption by a solution of CDPB (3) in n-hexane is at 339 mn, while its crystals show excitation maximum at 414 nm. However, in solution, the excitation spectra are quite similar. Further, the excitation spectra of crystalline DPB (2) and CMDPB (4) are much broader and considerably blue shifted relative to what of CDPB (3). The difference in the photophysical behavior is related to the crystal structure differences and reactivity differences. The results are discussed in terms of the possible involvement of either excimers or ground state molecular aggregates in the observed photoprocesses.

  DOI：

  10.1021/jp962952q
• 作为产物：
  描述：

  苯乙腈 、 肉桂醛 生成 (2Z,4E)-2,5-diphenylpenta-2,4-dienenitrile
  参考文献：
  名称：

  Kasatkin, A. N.; Biktimirov, R. Kh.; Tolstikov, G. A., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 6.1, p. 1037 - 1045

  摘要：

  DOI：

文献信息

• Facile Preparation of α-Cyano-α,ω-Diaryloligovinylenes: A New Class of Color-Tunable Solid Emitters
  作者：Peng An、Nian-Sheng Xu、Hao-Li Zhang、Xiao-Ping Cao、Zi-Fa Shi、Wei Wen

  DOI：10.1002/asia.201500473

  日期：2015.9

  reaction was used to construct a series of α‐cyano‐α,ω‐diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties, we found that the diene structure showed superior solid‐state luminescence. Furthermore, the emission color could be adjusted by introducing donor or acceptor functional groups at the

  有效的Knoevenagel缩合反应用于构建一系列的α-氰基-α，ω-二芳基寡聚谷氨酰胺，它们在固态下显示出显着的荧光发射。在研究共轭长度对荧光性质的影响时，我们发现二烯结构显示出优异的固态发光。此外，可以通过在末端芳基上引入供体或受体官能团来调节发光颜色。通过向α-氰基-α，ω-二芳基二亚乙烯基部分添加不同的官能团，可以实现可见光区域的全色发射。阐明了结构与属性之间的关系，并讨论了一些观察结果，例如取代位置效应。
• Practical Synthesis of (<i>Z</i>)-α,β-Unsaturated Nitriles via a One-Pot Sequential Hydroformylation/Knoevenagel Reaction
  作者：Yanxin Jiang、Chao Li、Songbai Tang、Shaokun Tao、Maolin Yuan、Ruixiang Li、Hua Chen、Haiyan Fu、Xueli Zheng

  DOI：10.1021/acs.joc.1c01953

  日期：2021.11.5

  Herein, the synthesis of (Z)-α,β-unsaturated nitriles by a sequential hydroformylation/Knoevenagel reaction has been first developed. A variety of crude α-olefins from Fischer–Tropsch synthesis, internal and special olefins, as well as alkynes could be transformed into value-added alkenyl nitriles (39 examples) up to 90% yield. Remarkably, compared with commonly used tedious multistep reactions, the

  在此，首次开发了通过顺序加氢甲酰化/Knoevenagel 反应合成 ( Z )-α,β-不饱和腈。来自费-托合成的各种粗α-烯烃、内烯烃和特殊烯烃以及炔烃可以转化为增值的烯基腈（39 个例子），产率高达 90%。值得注意的是，与常用的繁琐的多步反应相比，一锅法的特点是原料便宜且容易获得，具有优异的化学选择性、区域选择性和立体选择性，反应条件非常温和，易于放大生产。
• Manganese Catalyzed α-Olefination of Nitriles by Primary Alcohols
  作者：Subrata Chakraborty、Uttam Kumar Das、Yehoshoa Ben-David、David Milstein

  DOI：10.1021/jacs.7b06993

  日期：2017.8.30

  Catalytic α-olefination of nitriles using primary alcohols, via dehydrogenative coupling of alcohols with nitriles, is presented. The reaction is catalyzed by a pincer complex of an earth-abundant metal (manganese), in the absence of any additives, base, or hydrogen acceptor, liberating dihydrogen and water as the only byproducts.

  介绍了通过醇与腈的脱氢偶联，使用伯醇催化 α-烯化腈。该反应由富含地球的金属（锰）的钳状络合物催化，不存在任何添加剂、碱或氢受体，释放出氢和水作为唯一的副产物。
• Reconstructed Hydrotalcite as a Highly Active Heterogeneous Base Catalyst for Carbon−Carbon Bond Formations in the Presence of Water
  作者：Kohki Ebitani、Ken Motokura、Kohsuke Mori、Tomoo Mizugaki、Kiyotomi Kaneda

  DOI：10.1021/jo060345l

  日期：2006.7.1

  reaction of carbonyl compounds is efficiently catalyzed by reconstructed hydrotalcites, obtained by treating the Mg−Al mixed oxide with water, as solid base catalysts in the presence of water. The catalysis of the reconstructed hydrotalcites is attributable to the surface base sites, created during the organization of the layered structure, with uniformly distributed strength. Furthermore, the reconstructed

  羰基化合物的醛醇缩合反应可通过重构水滑石有效催化，该水滑石是通过在水中存在的情况下将Mg-Al混合氧化物与水作为固体基础催化剂进行处理而获得的。重构的水滑石的催化归因于表面碱位，其在层状结构的组织期间产生，具有均匀分布的强度。此外，重建的水滑石提供了独特的酸碱双功能表面，能够促进腈与羰基化合物的Knoevenagel和Michael反应。
• Metal‐Free Direct C−H Cyanation of Alkenes
  作者：Xi Wang、Armido Studer

  DOI：10.1002/anie.201807303

  日期：2018.9.3

  A metal‐free and direct alkene C−H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and trimethylsilyl cyanide as the cyanide source. This C−H functionalization can be conducted on gram scale, and for noncyclic 1,1‐ and 1,2‐disubstuted alkenes

  描述了无金属的直接烯烃CH氰化。不需要导向基团，并且该机理涉及通过由[双（三氟乙酰氧基）碘]芳烃和三甲基甲硅烷基氰化物作为氰化物源原位产生的氰基碘（III）物质对烯烃的亲电子活化。这种CH功能化可以以克为单位进行，对于非环状1,1,1，和1,2-二取代的烯烃，可以实现高立体选择性，因此使该方法具有很高的价值。