N-(prop-2-yn-1-yl)prop-2-ynamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(prop-2-yn-1-yl)prop-2-ynamide
• 英文别名: N-Prop-2-ynylpropynamide；N-propargylpropiolamide；N-prop-2-ynylprop-2-ynamide
• 化学式: C₆H₅NO
• 分子量: 107.112
• InChiKey: IJBRZAUIAANDGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(prop-2-yn-1-yl)prop-2-ynamide 在 Amberlyst A-21 supported CuI 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-{4-[({1-[2-(benzyloxy)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methyl)carbamoyl]-1H-1,2,3-triazol-1-yl}ethyl acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes

  摘要：

  In order to find new molecules with cytotoxic activity against cancer cells, we prepared bis-akyne amides derived from propiolic acid. The bis-alkynes were then transformed in their mono-1,2,3-triazole analogs onto the amide side, due to its greater reactivity, using a catalyst-free Huisgen's reaction. The mono-triazoles were then subjected to the copper (I)-catalyzed version of the previous reaction (CuAAC), using a supported catalyst, to produce bis-triazoles. All products were obtained pure after simple trituration or filtration procedures. All synthetic compounds were tested in vitro for their cytotoxic activity using B16 melanoma cells. Four compounds (7, 23, 25 and 33) showed activities in the micromolar range (<21 mu M) whereas three compounds (3, 22 and 38) presented activity at low micromolar concentrations (<10 mu M), and two analogs (2 and 13) were active at nanomolar levels (<1 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.025
• 作为产物：
  描述：

  炔丙胺 、 丙炔酸乙酯 在 Candida antarctica lipase B 作用下， 以 1,4-二氧六环 为溶剂， 以95%的产率得到N-(prop-2-yn-1-yl)prop-2-ynamide
  参考文献：
  名称：

  脂肪酶与丙酸乙酯的脂肪酶催化反应作为制备N-取代丙丙酰胺的途径的研究

  摘要：

  以苄胺为参比胺，研究了脂肪胺与丙酸乙酯的脂肪酶催化反应。优化条件以有利于1，2-加成，即形成N-苄基丙-2-炔酰胺，而不是1，4-加成。发现固定化的南极假丝酵母脂肪酶（CALB）是最有效的酶，并且反应在溶剂中进行，例如t BME，二恶烷或甲苯。该方法用于从脂肪族胺以良好至优异的产率制备丙丙酰胺。在相同条件下比较了O-和S-亲核试剂的反应性。

  DOI：

  10.1016/j.tet.2013.04.093

文献信息

• [EN] PROCESS FOR PREPARING N-H OR N-ALKYL 2-PROPYNAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE N-H- OU N-ALKYL-2-PROPYNAMIDE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014037308A1

  公开（公告）日：2014-03-13

  Disclosed is a method for the synthesis of N-H or N-alkyl 2-propynamides useful as intermediate in the manufacture of pharmaceutically active ingredients.

  揭示了一种合成N-H或N-烷基-2-丙炔酰胺的方法，该方法在制造药用活性成分中起中间体作用。
• UMSYMMETRICAL BISAZIDES FOR CHEMOSELECTIVE SEQUENTIAL LIGATION
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20140018541A1

  公开（公告）日：2014-01-16

  Unsymmetrical bisazides containing chelating and non-chelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with an excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.

  含有螯合和非螯合偶氮基团的不对称双偶联物可通过选择性化学反应，在两种不同的炔烃分子中，与三元铜(I)催化偶联反应发生反应。结合芳香族和脂肪族炔烃之间的反应性差异，通过在单个反应容器中混合两种炔烃和一个双偶氮基团，可以生成一个具有极佳区域选择性的双三唑分子。这种方法适用于中性pH值的水溶液中，可能在生物偶联应用中发挥作用。
• Co-cyclizations of nitrogen-containing acetylenes induced by a nickel triphenylphosphine complex to give aminoindane, isoindoline and isoindolinone derivatives
  作者：D. Malcolm Duckworth、Simon Lee-Wong、Alexandra M. Z. Slawin、Edward H. Smith、David J. Williams

  DOI：10.1039/p19960000815

  日期：——

  N-Methyl-, N,N-dimethyl-, N,N-diethylprop-2-ynylamines, N-prop-2-ynylacetamide and N-prop-2-ynylbenzamide are co-cyclized with diethyl hepta-1,6-diyne-4,4-dicarboxylate at room temperature in the presence of stoichiometric nickel(0) to give amino- and amido-indanes in fair to good yields. The structure of the product from N-prop-2-ynylbenzamide was established by X-ray crystallography. Likewise, N-alkyldiprop-2-ynylamines co-cyclize with methyl prop-2-ynyl ether to give isoindolines albeit in lower yields; the corresponding reaction of short chain N-alkynylalkynamides requires heating to 60 °C but gives isoindolinones and a 1,4-dihydroisoquinolin-3(2H)-one as mixtures of regioisomers in good yields. Attempts to synthesize medium-ring, benzo-fused lactams by this method failed.

  在室温下，N-甲基、N,N-二甲基、N,N-二乙基丙-2-炔胺、N-丙-2-炔基乙酰胺和 N-丙-2-炔基苯甲酰胺与庚-1,6-二炔-4,4-二甲酸二乙酯在等当量镍（0）存在下发生共环化反应，得到氨基和脒基茚类化合物，收率从一般到良好。通过 X 射线晶体学，确定了 N-丙-2-炔基苯甲酰胺的产物结构。同样，N-烷基二丙基-2-炔胺与甲基丙-2-炔基醚发生共环化反应，生成异吲哚啉，但产率较低；短链 N-炔基炔酰胺的相应反应需要加热至 60 °C，但以良好的产率生成异吲哚啉酮和 1,4-二氢异喹啉-3(2H)-酮的区域异构体混合物。用这种方法合成中环苯并内酰胺的尝试失败了。
• Chemoselective preparation of disymmetric bistriazoles from bisalkynes
  作者：Hichem Elamari、Faouzi Meganem、Jean Herscovici、Christian Girard

  DOI：10.1016/j.tetlet.2010.11.141

  日期：2011.2

  Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen's reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. (C) 2010 Elsevier Ltd. All rights reserved.
• On the reactivity of activated alkynes in copper and solvent-free Huisgen’s reaction
  作者：Hichem Elamari、Ibtissem Jlalia、Charlotte Louet、Jean Herscovici、Faouzi Meganem、Christian Girard

  DOI：10.1016/j.tetasy.2010.06.013

  日期：2010.5

  Terminal alkynes substituted by a carbonyl-type electron-withdrawing group have been found to undergo Huisgen's cycloaddition with azides at room temperature in a solvent-free manner; without a need of either heating or catalysis. Metallic salts, other than the copper ones also efficiently catalyzed the reactions. The yields were good and the products isolated mainly as their 1,4-disubstituted isomer. (C) 2010 Elsevier Ltd. All rights reserved.