1-(non-2-yn-1-yl)piperidine | 1169866-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(non-2-yn-1-yl)piperidine
• 英文别名: 1-(Non-2-yn-1-yl)piperidine；1-non-2-ynylpiperidine
• CAS: 1169866-30-1
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: HJJCCINQBXFQSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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-(non-2-yn-1-yl)piperidine 、 环庚三烯 在 二氯二(戊烷-2,4-二酮酸根-O,O')钛 、 氯化二乙基铝 作用下， 以 苯 为溶剂， 反应 8.0h， 以88%的产率得到1-[(8-hexylbicyclo[4.2.1]nona-2,4,7-trien-7-yl)methyl]piperidine
  参考文献：
  名称：

  Catalytic [6π+2π]-cycloaddition of alkynes, 1,2- and 1,3-dienes to 1,3,5-cycloheptatrienes involving Ti complexes

  摘要：

  Novel two-component Ti-based catalytic systems, R2TiCl2 R'nAlCl(3-n) (R=acac, (PrO)-Pr-i, (BuO)-Bu-t; R'=Et, Bu, n=2, 3), for [6 pi+2 pi]-cycloaddition of acetylenes and 1,2- and 1,3-dienes, including functionally substituted ones, to 1,3,5-cycloheptatrienes to give bi-, tri-, and polycyclic hydrocarbons were developed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.019
• 作为产物：
  描述：

  二哌啶甲烷 、 1-辛炔 在 copper(l) chloride 作用下， 反应 6.0h， 以68%的产率得到1-(non-2-yn-1-yl)piperidine
  参考文献：
  名称：

  Synthesis of 2,3-acetylenic amines by aminomethylation of acetylenes with geminal diamines

  摘要：

  A general and effective procedure has been developed for the synthesis of symmetrical and unsym- metrical 2,3-acetylenic amines by aminomethylation of terminal mono- and diacetylenes with geminal diamines in the presence of transition metal salts and complexes.

  DOI：

  10.1134/s1070428010010021

文献信息

• 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.
• InBr3-catalyzed three-component reaction: a facile synthesis of propargyl amines
  作者：J.S. Yadav、B.V. Subba Reddy、A.V. Hara Gopal、K.S. Patil

  DOI：10.1016/j.tetlet.2009.03.014

  日期：2009.7

  Indium(III) bromide has been used for the first time for the synthesis of propargyl amines in a one-pot operation from aldehydes, amines and alkynes. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of 2,3-acetylenic amines by aminomethylation of acetylenes with geminal diamines
  作者：M. G. Shaibakova、I. G. Titova、G. A. Makhmudiyarov、A. G. Ibragimov、U. M. Dzhemilev

  DOI：10.1134/s1070428010010021

  日期：2010.1

  A general and effective procedure has been developed for the synthesis of symmetrical and unsym- metrical 2,3-acetylenic amines by aminomethylation of terminal mono- and diacetylenes with geminal diamines in the presence of transition metal salts and complexes.
• Catalytic [6π+2π]-cycloaddition of alkynes, 1,2- and 1,3-dienes to 1,3,5-cycloheptatrienes involving Ti complexes
  作者：Usein M. Dzhemilev、Gulnara N. Kadikova、Dmitry I. Kolokol'tsev、Vladimir A. D'yakonov

  DOI：10.1016/j.tet.2013.04.019

  日期：2013.6

  Novel two-component Ti-based catalytic systems, R2TiCl2 R'nAlCl(3-n) (R=acac, (PrO)-Pr-i, (BuO)-Bu-t; R'=Et, Bu, n=2, 3), for [6 pi+2 pi]-cycloaddition of acetylenes and 1,2- and 1,3-dienes, including functionally substituted ones, to 1,3,5-cycloheptatrienes to give bi-, tri-, and polycyclic hydrocarbons were developed. (C) 2013 Elsevier Ltd. All rights reserved.