3-(萘-1-基氨基)丙腈 | 36710-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(萘-1-基氨基)丙腈
• 英文名称: N-cyanoethyl-1-naphthylamine
• 英文别名: β-(1-naphthylamino)propionitrile；3-((1-naphthyl)amino)propanenitrile；N-[1]naphthyl-β-alanine nitrile；N-[Napthyl-(1)-β-alanin-nitril；N-[1]Naphthyl-β-alanin-nitril；3-(Naphthalen-1-ylamino)propanenitrile
• CAS: 36710-68-6
• 化学式: C₁₃H₁₂N₂
• mdl: MFCD11164277
• 分子量: 196.252
• InChiKey: DVWXBMMYPRDXQG-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  421.5±28.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(萘-1-基氨基)丙腈 在 硫酸 、 sodium nitrite 作用下， 反应 10.0h， 生成 3-[(4-Nitrosonaphthalen-1-yl)amino]propanenitrile
  参考文献：
  名称：

  On the Nitrosation ofN-monosubstituted 1-naphthylamines - formation ofN-monosubstituted 4-nitroso-1-naphthylamine derivatives and benzocondensed indaminium salts

  摘要：

  By nitrosation of the mineralic acid salts of N-monosubstituted 1-naphthylamines (7) N-monosubstituted N'-hydroxy-naphthoquinone diiminium salts (9) are formed. These compounds can condense with their naphthylamine educts 7 to deeply colored N-(4-amino-naphthyl)-substituted naphthoquinone diiminium salts 11 which are available by the reaction of the mineralic acid salts of N-monosubstituted 1-naphthylamines 7 with one half equivalent of nitrous acid in acetic acid solution also. The new indaminium salts 11 absorb, in contrast to their deprotonated species 12 which exhibit intense absorption bands at about 550 nm, in the near infrared region very intensively at about 820 nm.

  DOI：

  10.1002/prac.19963380181
• 作为产物：
  描述：

  1-萘胺 、 丙烯腈 在 aluminum oxide 作用下， 反应 8.0h， 以75%的产率得到3-(萘-1-基氨基)丙腈
  参考文献：
  名称：

  在碱性Al 2 O 3中向缺电子的烯烃中有效地将芳族胺氮杂-迈克尔加成

  摘要：

  在室温下，使用碱性Al 2 O 3作为固体介质，对芳香族或脂肪族胺与各种缺电子的烯烃进行Aza-Michael加成反应，得到了相应的Michael加成产物，收率良好至极佳。碱性Al 2 O 3可以容易地回收和再利用。

  DOI：

  10.1016/j.tet.2010.05.054

文献信息

• Synthesis, Characterization and Catalytic Application of MCM 41 Supported Phenanthrolinium Dibromide Catalyst for Aza-Michael Addition Reaction in Aqueous Medium
  作者：Rahman Hosseinzadeh、Nora Aghili、Mahmood Tajbakhsh

  DOI：10.1007/s10562-016-1743-4

  日期：2016.7

  MCM-41 immobilized phenanthrolinium dibromide (phen-MCM-Br2) was easily prepared and applied as an efficient heterogeneous catalyst for aza-Michael addition of aromatic amines to α,β-unsaturated nitriles and nitro compounds in water. The catalyst was characterized by CHN, TGA, FT-IR, SEM, EDAX, XRD, BET, and TEM. It could be simply recovered and reused several times without significant loss of catalytic

  MCM-41 固定化二溴化菲啉 (phen-MCM-Br2) 很容易制备并用作有效的多相催化剂，用于芳香胺与水中 α,β-不饱和腈和硝基化合物的氮杂-迈克尔加成反应。通过CHN、TGA、FT-IR、SEM、EDAX、XRD、BET和TEM对催化剂进行表征。它可以简单地回收和重复使用多次而不会显着损失催化活性。图形摘要
• Yttrium nitrate promoted selective cyanoethylation of amines
  作者：Arunava Misra、SK Rajibul Haque、Mohabul A Mondal

  DOI：10.1007/s12039-023-02173-2

  日期：——

  various aromatic and aliphatic amines with acrylonitrile at ambient temperature in a protic solvent. The method is selective for the monocyanoethylation of primary aromatic amines, aliphatic secondary amines, and sterically hindered aliphatic amines. Phenols and active methylene compounds do not undergo cyanoethylation. Thiophenol, in the presence of yttrium nitrate, promotes the polymerization of

  催化剂Y(NO 3 ) 3 , 6H 2 O在常温质子溶剂中，在各种芳香胺和脂肪胺与丙烯腈的氮杂迈克尔加成反应中表现出显着的活性。该方法对伯芳香胺、脂肪族仲胺和空间位阻脂肪胺的单氰乙基化具有选择性。酚类和活性亚甲基化合物不会发生氰乙基化。苯硫酚在硝酸钇存在下促进丙烯腈的聚合。水溶性和高催化剂稳定性使从产品中去除催化剂的过程变得容易。直接对反应混合物进行水处理可以分离出纯度高达 99.9% 的氰乙基化产物。 图形概要 芳香伯胺选择性单氰乙基化，尤其是富电子芳香胺 在碳和氧亲核试剂存在下具有出色的区域选择性 报道的条件可用于在苯硫酚存在下聚合丙烯腈。 富电子芳香胺容易反应。 对氮中心的空间效应高度敏感
• Lanthanoids in Hydroarylaminations: Yb(III)- and Tb(III)-Catalyzed Addition of Arylamines to Activated Olefins
  作者：Rajesh Kunjanpillai、Rajagopal Rajesh、Olencheri Karimpanakkal Sandhya、Sunilkumar Puthenpurackal Narayanan

  DOI：10.1055/a-2282-7702

  日期：——

  Yb(OTf)3 and Tb(OTf)3 to give the desired β-aminonitriles, β-amino sulfones, and dimethyl aspartates, respectively, in moderate to excellent yields. The reactions were carried out in toluene for Yb(OTf)3 and in t-BuOMe for Tb(OTf)3, all reactions were performed at 100 °C.

  使用 Yb(OTf) 3和 Tb(OTf) 3独立催化的芳基胺实现丙烯腈、苯基乙烯基砜和马来酸二甲酯的迈克尔型氢胺化，分别得到所需的 β-氨基腈、β-氨基砜和天冬氨酸二甲酯，中等至优异的产量。 Yb(OTf) 3 的反应在甲苯中进行， Tb(OTf) 3 的反应在t -BuOMe中进行，所有反应均在100℃下进行。
• Preparation and Characterization of Bridged Naphthoxazinium Salts
  作者：Andreas Kanitz、Horst Hartmann

  DOI：10.1002/(sici)1099-0690(199904)1999:4<923::aid-ejoc923>3.0.co;2-n

  日期：1999.4

  By condensation of bridged 4-arylazo-substituted 3-hydroxyanilines 18 and bridged or unbridged 4-arylazo-substituted 1-naphthylamines 19-23 with bridged 1-naphthylamines 15-17 and 3-aminophenols 14, respectively, in the presence of perchloric acid, bridged naphthoxazinium perchlorates 24-30 have been prepared. The spectral properties of the products have been compared with those of the bridged phenoxazinium salt 31 as well as with data for some unbridged analogues.
• 40. Experiments on the synthesis of aza-steroids. Part I
  作者：G. R. Clemo、L. K. Mishra

  DOI：10.1039/jr9530000192

  日期：——