2-(naphthalene-1-yl)pentanenitrile | 56477-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalene-1-yl)pentanenitrile
• 英文别名: 2-(naphth-1-yl) valeronitrile；2-naphthalen-1-yl-pentanenitrile；α-Propyl-(1-naphthyl)-acetonitril；2-(Naphthyl-1)-valeronitril；2-Naphthalen-1-ylpentanenitrile
• CAS: 56477-49-7
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: WMMGUIVUDXKRLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-(naphthalene-1-yl)pentanenitrile 在 sodium hydroxide 、 苄基三乙基氯化铵 、 氧气 作用下， 反应 6.0h， 以51%的产率得到1-萘-1-基丁烷-1-酮
  参考文献：
  名称：

  Phase-Transfer Catalyzed Oxidative Decyanation of α-Secondary Nitriles; A Convenient Synthesis of Aromatic Ketones

  摘要：

  DOI：

  10.1055/s-1980-29301
• 作为产物：
  描述：

  1-萘-1-基丁烷-1-酮 、 对甲基苯磺酰甲基异腈 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 、 叔丁醇 为溶剂， 以35%的产率得到2-(naphthalene-1-yl)pentanenitrile
  参考文献：
  名称：

  Synthesis of β-Substituted Naphth-1-yl Ethylamido Derivatives as New Melatoninergic agonists

  摘要：

  Naphthalene melatoninergic ligands with alkyl groups (Me, Et, Pr, Bz) in the beta position of the ethylamido chain were synthesised. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand. An increase in the affinity was observed with the beta-methyl derivatives and the greatest increase was seen with the (-) enantiomers. The introduction of a 2- or 7-MeO group on the naphthalene ring and the lengthening (Et, Pr) of the alkylamido chain gave potent compounds such as (-)1h (K-i = 24 pM). The functional activity of these compounds was evaluated by the aggregation of melanophores in Xenopus laevis tadpoles. The potency to produce lightening of the skin of Xenopus laevis was related to the affinities values of the molecules at melatonin chicken brain receptors. The most potent ligands were found to be full agonists and compound 1h was 25 fold more potent than melatonin in this bioassay. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00236-9

文献信息

• Novel α-arylnitriles synthesis via Ni-catalyzed cross-coupling of α-bromonitriles with arylboronic acids under mild conditions
  作者：Yingying Yang、Shan Tang、Chao Liu、Huimin Zhang、Zhexun Sun、Aiwen Lei

  DOI：10.1039/c1ob05326d

  日期：——

  An applicable and easy-handling Ni-catalyst can be used to promote direct arylation of α-bromonitriles with various arylboronic acids to construct α-arylnitriles under mild conditions. The methodology tolerates β-hydrogens and functional groups in the substrates.

  一种适用且易于操作的镍催化剂可用于促进α-溴腈与各种芳基硼酸的直接芳基化反应，在温和条件下构建α-芳基腈。这一方法对底物中的β-氢和官能团具有良好的耐受性。
• Synthesis and antiarrhythmic activity of naphthylalkylamines
  作者：Gianfranco. Pala、Arturo. Donetti、Carla. Turba、Silvano. Casadio

  DOI：10.1021/jm00298a020

  日期：1970.7.1
• DONETTI A.; BONIARDI O.; EZHAYA A., SYNTHESIS, 1980, NO 12, 1009-1011
  作者：DONETTI A.、 BONIARDI O.、 EZHAYA A.

  DOI：——

  日期：——
• MAKOSZA M.; LUDWIKOW M.; URNIAZ A., ROCS. CHEM. <ROCH-AC>, 1975, 49, NO 2, 297-306
  作者：MAKOSZA M.、 LUDWIKOW M.、 URNIAZ A.

  DOI：——

  日期：——
• Phase-Transfer Catalyzed Oxidative Decyanation of α-Secondary Nitriles; A Convenient Synthesis of Aromatic Ketones
  作者：Arturo Donetti、Orazio Boniardi、Antoine Ezhaya

  DOI：10.1055/s-1980-29301

  日期：——