1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine | 125014-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine
• 英文别名: 1-[3-(naphthalen-1-yl)prop-2-yn-1-yl]piperidine；1-(3-Naphthalen-1-ylprop-2-ynyl)piperidine
• CAS: 125014-56-4
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: OFVNYRMEVCAAMD-UHFFFAOYSA-N

物化性质

• 沸点：
  197 °C(Press: 5 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine 在 氢氧化钾 作用下， 以 乙醚 、 水 为溶剂， 生成 Spiro[8,10-dihydronaphtho[1,2-f]isoindol-9-ium-9,1'-azinan-1-ium];bromide
  参考文献：
  名称：

  Synthesis of new condensed analogs of isoindolinium salts

  摘要：

  DOI：

  10.1007/bf00472504
• 作为产物：
  描述：

  哌啶 、 二氯甲烷 、 1-乙炔基萘 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cobalt(II) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以88%的产率得到1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine
  参考文献：
  名称：

  org/10.1016/j.tetlet.2012.08.136

  摘要：

  DOI：

  org/10.1016/j.tetlet.2012.08.136

文献信息

• Effect of substituents in the propynyl fragment and at the nitrogen atom on the intramolecular cyclization of (3-aryl-2-propynyl)-(4-hydroxy- 2-butynyl)ammonium chlorides and also on the recyclization of the products formed
  作者：A. A. Khachatryan

  DOI：10.1007/s10593-011-0879-9

  日期：2011.12

  l)piperazinium- and dicyclohexylammonium chlorides. In addition to the cyclization products - corresponding dialkyl(7-hydroxymethyl)naphtho[1,2-f]isoindolinium or dialkyl-(4-hydroxy-methyl)benzo[f]isoindolinium chlorides, the products of recyclization of these – dialkyl-amino-phenanthro[1,2-c]furan or dialkylaminonaphtho[1,2-c]furan are also formed. The indicated derivatives become the main products

  与KOH水溶液相比，在更严格的条件下（盐与碱的比例为1：1），使用KOH水溶液使二烷基（4-羟基-2-丁炔基）[3-（α-萘基）-2-丙炔基]氯化铵环化它们的3-苯基（对氯苯基，链烯基）取代的类似物（盐与KOH的比例为5∶1）。类似地，对于（4-羟基-2-丁炔基）-（3-苯基-2-丙炔基）哌嗪氯化物和二环己基氯化铵的环化也需要更严格的条件。除了环化产物-相应的二烷基（7-羟甲基）萘[1,2-f]异吲哚鎓或二烷基-（4-羟基甲基）苯并[f]异吲哚鎓氯化物外，这些环化产物还包括–二烷基氨基还形成了-邻菲并[1,2-c]呋喃或二烷基氨基萘并[1,2-c]呋喃。通过将盐与KOH之比改变为1∶2，并且随着反应时间的增加，所示的衍生物成为起始盐转化的主要产物。与类似的苯并[f]异吲哚鎓体系相比，空间效应以及所获得的萘并[1,2-f]异吲哚鎓盐体系的较低热稳定性可以解释所获得的结果。。
• Intramolecular Cycloaddition of [3-(Naphthalen-1-yl)prop-2-yn-1-yl](3-phenylprop-2-en-1-yl)ammonium Bromides and Cleavage of Some of the Obtained Cyclic Salts in Aqueous Alkali
  作者：E. O. Chukhajian、L. V. Ayrapetyan、K. G. Shahkhatuni、H. S. Mkrtchyan、H. A. Panosyan

  DOI：10.1134/s1070428020120064

  日期：2020.12

  op-2-yn-1-yl](3-phenylprop-2-en-1-yl)ammonium bromide under very mild conditions afforded potentially biologically active 4-phenyl-3a,4-dihydronaphtho[f]isoindolium salts in high yields. Some of the synthesized salts underwent cleavage on heating in aqueous alkali to give mixtures of isomeric aminomethylphenanthrenes.

  摘要 在非常温和的条件下，[3-（萘-1-基）丙-2-炔-1-基]（3-苯基丙-2-烯-1-基）溴化铵的分子内环加成反应会产生潜在的生物活性4-苯基- 3a，4-二氢萘并[ f ]异吲哚鎓盐产率高。一些合成的盐在碱水溶液中加热裂解，得到异构体氨基甲基菲的混合物。
• Synthesis of 1-[(1,1′-biphenyl)-4-yl]naphthalene from amines obtained by the Stevens rearrangement of N-[3-(naphthalen-1-yl)prop-2-yn-1-yl]-3-phenylprop-2-en-1-aminium bromides
  作者：E. O. Chukhajian、L. V. Ayrapetyan、G. A. Panosyan

  DOI：10.1007/s11172-022-3528-9

  日期：2022.6

  A convenient procedure to access 1-[(1,1′-biphenyl)-4-yl]naphthalene by the Stevens rearrangement of the aminium salts bearing simultaneously 3-phenylprop-2-enyl and [3-(α-naphthyl)prop-2-ynyl] moieties was developed. During vacuum distillation, the synthesized compounds underwent the domino reaction to afford 1-[(1,1′-biphenyl)-4-yl]naphthalene. On the first step of this reaction, β-elimination of

  通过史蒂文斯重排，同时带有3-苯基丙-2-烯基和[3-(α-萘基)丙-2-炔基]部分的氨基盐，可以方便地合成1-[(1,1′-联苯)-4-基]萘。在真空蒸馏过程中，合成的化合物发生多米诺反应，生成1-[(1,1′-联苯)-4-基]萘。在反应的第一步，仲胺的β-消除反应生成共轭二烯炔；在第二步，二烯炔的电环反应生成环烯丙基中间体；在第三步，烯丙基中间体通过1,3-或1,5-氢位移迅速转化为1-[(1,1′-联苯)-4-基]萘。
• Bridging homogeneous and heterogeneous catalysis with MOFs: Cu-MOFs as solid catalysts for three-component coupling and cyclization reactions for the synthesis of propargylamines, indoles and imidazopyridines
  作者：I. Luz、F.X. Llabrés i Xamena、A. Corma

  DOI：10.1016/j.jcat.2011.10.001

  日期：2012.1

  Copper-containing MOFs are found to be active, stable and reusable solid catalysts for three-component couplings of amines, aldehydes and alkynes to form the corresponding propargylamines. Two tandem reactions, including an additional cyclization step, leads to the effective production of indoles and imidazopyridines. In particular, the lamellar compound [Cu(BDC)] (BDC = benzene dicarboxylate) is highly efficient for the preparation of imidazopyridines, although a progressive structural change of the solid to a catalytically inactive compact structure is produced, causing deactivation of the catalyst. Nevertheless, the phase change can be reverted by refluxing in DMF, which recovers the original lamellar structure and the catalytic activity of the fresh material. The use of [Cu(BDC)] for this reaction also prevents the formation of Glaser/Hay condensation products of the alkyne, even when the reaction is performed in air atmosphere. This is a further advantage of [Cu(BDC)] with respect to other homogeneous copper catalysts, for which the use of an inert atmosphere is necessary. (C) 2011 Elsevier Inc. All rights reserved.
• Synthesis of dialkyltetrahydrobenz[f]iso-indoline, dialkyl-4-??-cyclohexenylbenz[f]iso-indoline, and dimethyl-4-alkenylnaphth[f]iso-indolive salts through base-catalyzed intramolecular cyclization of quaternary ammonium salts
  作者：�. O. Chukhadzhyan、�l. O. Chukhadzhyan、K. G. Shakhatuni、N. T. Gevorkyan、A. T. Babayan

  DOI：10.1007/bf01169243

  日期：1996.3