2-(2-methoxynaphthalen-1-yl)acetonitrile | 71056-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-methoxynaphthalen-1-yl)acetonitrile
• 英文别名: (2-methoxy-naphth-1-yl)acetonitrile；2-Methoxy-1-naphthaleneacetonitrile；(2-methoxy-[1]naphthyl)-acetonitrile；(2-Methoxy-[1]naphthyl)-acetonitril；(2-Methoxy-naphthyl-(1))-essigsaeure-nitril；2-methoxy-naphthalene-1-acetonitrile
• CAS: 71056-97-8
• 化学式: C₁₃H₁₁NO
• mdl: MFCD09923869
• 分子量: 197.236
• InChiKey: HNRJVFNBFXVKHX-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  363.2±17.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-methoxynaphthalen-1-yl)acetonitrile 在 盐酸 、 氢气 、 镍 、 sodium hydride 、 三乙胺 作用下， 以 ammonium hydroxide 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成
  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
• 作为产物：
  描述：

  (6-溴-2-甲氧基-1-萘基)乙腈 在 三正丁基氢锡 作用下， 反应 4.0h， 以50%的产率得到2-(2-methoxynaphthalen-1-yl)acetonitrile
  参考文献：
  名称：

  The chloromethylation of 1-bromo-2-methoxynaphthalene. A revised structure for the product

  摘要：

  DOI：

  10.1021/jo00199a048

文献信息

• Preparation of Indolenines via Nucleophilic Aromatic Substitution
  作者：Florian Huber、Joel Roesslein、Karl Gademann

  DOI：10.1021/acs.orglett.9b00489

  日期：2019.4.19

  An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples

  描述了一种不寻常的芳族取代基来取代吲哚。使2-（2-甲氧基苯基）乙腈衍生物与各种烷基和芳基Li试剂反应以提供相应的吲哚烯产物，天然产物的成分和花青染料，例如吲哚花青绿。该新方法用于合成具有较大官能团耐受性的41种吲哚胺，并将选定的实例进一步转化为相应的吲哚啉染料。关键实验提供了这种亲核芳族取代机理的见解。
• Organo-photoredox-Catalyzed Selective Mono- and Bis-C–H Alkylation of Electron-Rich (Hetero)Arenes
  作者：Shyamal Pramanik、Partha Pratim Mondal、Soumitra Maity

  DOI：10.1021/acs.joc.3c01757

  日期：2023.11.3

  under mild conditions. The extent of alkylation with alkyl bromides was found to be controlled by introducing Zn(OAc)2 as a bromide scavenger, ensuring the blocking of potential bromo-arene byproduct formation under photoredox conditions. In addition, a sequential C–H alkylation strategy for selective bis-alkylation has also been developed via chronological incorporation of different alkyl radical precursors

  在此，我们公开了一种利用可见光介导的有机光催化SET过程用烷基​​溴对富电子（杂）芳烃进行C-H烷基化的简单策略。该方法的通用性已通过在温和条件下包含各种烷基（α-烷基羰基、苄基、氰甲基）以及各种具有生物活性的富电子芳烃和（杂）芳烃得到证明。发现用烷基溴进行烷基化的程度可以通过引入Zn(OAc) 2作为溴化物清除剂来控制，确保阻止光氧化还原条件下潜在的溴代芳烃副产物的形成。此外，通过按时间顺序将不同的烷基自由基前体在一锅中相当有效地结合，还开发了用于选择性双烷基化的顺序C-H烷基化策略。
• Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 255
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Amine Replacement Reactions of α-Dimethylaminomethyl-β-methoxynaphthalene
  作者：H. R. Snyder、James H. Brewster

  DOI：10.1021/ja01171a083

  日期：1949.3
• 88. The preparation of diarylmaleonitriles
  作者：A. H. Cook、J. Downer、B. Hornung

  DOI：10.1039/jr9410000502

  日期：——