1‐amino‐3‐methyl‐4‐phenyl‐2‐naphthonitrile

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 1‐amino‐3‐methyl‐4‐phenyl‐2‐naphthonitrile
• 英文别名: 1-amino-3-methyl-4-phenyl-2-naphthalenecarbonitrile；1-amino-3-methyl-4-phenylnaphthalene-2-carbonitrile
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: PEZNGFOYAGSYKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苄基苯甲腈 在 palladium on activated charcoal 作用下， 以 various solvent(s) 为溶剂， 生成 1‐amino‐3‐methyl‐4‐phenyl‐2‐naphthonitrile
  参考文献：
  名称：

  通过连续的迈克尔加成/乙醇酸酯-腈偶联途径高效合成1-氨基-2-萘甲酸衍生物，并将其用于方便地制备芳基萘并呋喃酮木质素的9-氨基类似物。

  摘要：

  通过在二甘醇二甲醚中用LDA处理2-烷基苄腈与α，β-不饱和羧酸酯和腈反应原位生成的2-（α-硫代烷基）苄腈与1-氨基-3,4-二氢-2-萘甲酸乙酯和通过将硫代腈迈克尔加成到α，β-不饱和羧酸衍生物上，然后碘化锌促进分子内烯醇盐-腈偶联，生成的烯醇盐中间体以54-98％的产率形成腈。在回流的对甲基苯甲基中用活性炭上的钯脱氢，将二氢萘羧酸衍生物以43-99％的产率转化为相应的1-氨基-2-萘甲酸衍生物。随后，我们表明，通过使用类似的反应顺序，

  DOI：

  10.1021/jo961744r

文献信息

• Annulation of β-Enaminonitriles with Alkynes via Rh^III-Catalyzed C–H Activation: Direct Access to Highly Substituted 1-Naphthylamines and Naphtho[1,8-<i>bc</i>]pyridines
  作者：Haili Wang、Hong Xu、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.8b02341

  日期：2018.9.21

  A Cp*RhIII-catalyzed oxidative annulation of β-enaminonitriles with alkynes was reported to achieve selective synthesis of polysubstituted 1-naphthylamines and naphtho[1,8-bc]pyridines via multiple C–H activations. Assisted by a naphthylamine NH2 group, 1-naphthylamines were also readily cyclized to produce naphtho[1,8-bc]pyridines. In addition, the obtained naphtho[1,8-bc]pyridine derivatives exhibit

  据报道，Cp * Rh III催化的炔烃对β-烯腈的氧化环化反应通过多种C-H活化选择性地合成了多取代的1-萘胺和萘[1,8- bc ]吡啶。在萘胺NH 2基团的辅助下，1-萘胺也很容易被环化以生成萘[1,8- bc ]吡啶。此外，所获得的萘并[1,8- bc ]吡啶衍生物在固态下表现出强烈的荧光。
• An Efficient General Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives Based on a Tandem Conjugate Addtion-Enolate Nitrile Coupling Sequence
  作者：Kazuhiro Kobayashi、Keiichiro Takada、Hiroto Tanaka、Tomokazu Uneda、Tomohide Kitamura、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/cl.1996.25

  日期：1996.1

  Reaction of o-(α-lithioalkyl)benzonitriles with α,β-unsaturated carboxylic acid derivatives produced 1-amino-3,4-dihydro-2-naphthalenecarboxylic acid derivatives through the tandem conjugate addition-enolate nitrile coupling sequence, which in turn were converted into 1-amino-2-naphthalenecarboxylic acid derivatives on dehydrogenation with palladium on activated carbon.

  o-(α-锂烷基)苯腈与α,β-不饱和羧酸衍生物的反应通过串联的共轭加成-烯醇腈偶联序列生成1-氨基-3,4-二氢-2-萘甲酸衍生物，而这些衍生物在与活性炭铂的脱氢反应中进一步转化为1-氨基-2-萘甲酸衍生物。
• Novel synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones
  作者：Bartłomiej Kozik、Jarosław Wilamowski、Maciej Góra、Janusz J. Sepioł

  DOI：10.1016/j.tetlet.2006.03.054

  日期：2006.5

  A two-step synthesis of 1-amino-4-arylnaphthalene-2-carbonitriles from diphenylacetaldehydes and 1,1-diphenylacetones involves condensation of the carbonyl compounds with malonodinitrile and cyclization of the aryl-ylidenemalonodinitriles obtained in concentrated sulfuric acid. The benzannulation reaction is accompanied with a quasi-aromatic rearrangement. Some of synthesized aminonitriles reveal considerable biological activity against phytopathogenic fungi. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of α-arylnaphthalenes from diphenylacetaldehydes and 1,1-diphenylacetones
  作者：Bartłomiej Kozik、Jarosław Wilamowski、Maciej Góra、Janusz J. Sepioł

  DOI：10.1016/j.tet.2008.04.067

  日期：2008.6

  Condensation of diphenylacetalclehydes and 1,1-diphenylacetones with malonodinitrile and cyclization of obtained aryl-ylidenemalonodinitriles in concentrated sulfuric acid leads to 1-amino-4-arylnaphthalene-2-carbonitriles. The benzannulation reaction is accompanied by a quasi-aromatic rearrangement. Preliminary tests of some synthesized aminonitriles have revealed their considerable biological activity against phytopathogenic fungi. (c) 2008 Elsevier Ltd. All rights reserved.