N,N'-di-prop-2-ynyl-phthalamide | 943238-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-di-prop-2-ynyl-phthalamide
• 英文别名: N¹,N²-dipropargylphthalamide；1-N,2-N-bis(prop-2-ynyl)benzene-1,2-dicarboxamide
• CAS: 943238-51-5
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: CVKQSLXFUPLLMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-di-prop-2-ynyl-phthalamide 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以68%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-[[[2-[[1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazol-4-yl]methylcarbamoyl]benzoyl]amino]methyl]triazol-1-yl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of novel multidentate carbohydrate-triazole ligands

  摘要：

  Cu(I)-catalyzed 1,3-dipolar cycloaddition (click reaction) of 1 mol equiv of N,N'-di-prop-2-ynyl-phthalamide (1a), N,N'-di-prop-2-ynyl-isophthalamide (1b), and pyridine-2,6-dicarboxylic acid bis-prop-2-ynylamide (1c), respectively with 2 mol equiv of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide (2a), 2-azidoethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (2b), and 2-azidoethyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2c), respectively, afforded the corresponding bis-cycloadducts 3-5, containing two 1,2,3-triazole moieties each, in 38-76% yield. Reaction of 1 mol equiv of 2c with 1 mol equiv of le under otherwise identical conditions gave the mono-cycloadduct 6, containing one 1,2,3-triazole and one 2-propynylamide moiety, in 77% yield. Reaction of 6 with 2a afforded 7, containing two different sugar moieties, in 67% yield. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.081
• 作为产物：
  描述：

  N-propargylphthalyl monoamsolidide 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-di-prop-2-ynyl-phthalamide
  参考文献：
  名称：

  通过磺酰叠氮、末端炔烃和醇/胺的铜催化反应的有效闭环方法

  摘要：

  我们开发了一种通用的、高效的方法，通过铜催化磺酰叠氮化物、末端炔烃（或双炔烃）和醇/胺（二胺）在室温下的反应，该方法具有很强的实用性。进入各种中型和大型杂环。

  DOI：

  10.1055/s-2007-973883

文献信息

• 多价氮杂糖衍生物及其合成方法
  申请人：北京大学

  公开号：CN103373955B

  公开（公告）日：2016-04-06

  本发明提供一种具有通式(I)的3,4,5-三羟基-1-辛基哌啶-2-酮的多价氮杂糖的衍生物及其合成方法。本发明以(3S,4R,5S)-3,4,5-三羟基-1-(8-氨基辛基)哌啶-2-酮为单体与多元酸或多元酰氯及以(3S,4R,5S)-3,4,5-三羟基-1-(8-叠氮基辛基)哌啶-2-酮为单体与多元酸、多元醇或多元酰氯的衍生物连接形成多价氮杂糖。本发明合成的多价氮杂糖有作为治疗Gaucher病CMT（药理分子伴侣疗法）中药理分子伴侣的潜力，具有很高的应用价值。
• Efficient Ring-Closure Approach via Copper-Catalyzed Reactions of Sulfonyl Azide, Terminal Alkynes and Alcohols/Amines
  作者：Hua Fu、Ying Jin、Yingwu Yin、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2007-973883

  日期：2007.4

  We have developed a general and efficient method for synthesis of medium- and large-sized heterocycles via copper-catalyzed reactions of sulfonyl azide, terminal alkynes (or bisalkyne) and alcohols/amines (diamines) at room temperature, and the highly practical method provides an entry toward diverse medium- and large-sized heterocycles.

  我们开发了一种通用的、高效的方法，通过铜催化磺酰叠氮化物、末端炔烃（或双炔烃）和醇/胺（二胺）在室温下的反应，该方法具有很强的实用性。进入各种中型和大型杂环。
• Synthesis of novel multidentate carbohydrate-triazole ligands
  作者：Thomas Ziegler、Catrin Hermann

  DOI：10.1016/j.tetlet.2008.01.081

  日期：2008.3

  Cu(I)-catalyzed 1,3-dipolar cycloaddition (click reaction) of 1 mol equiv of N,N'-di-prop-2-ynyl-phthalamide (1a), N,N'-di-prop-2-ynyl-isophthalamide (1b), and pyridine-2,6-dicarboxylic acid bis-prop-2-ynylamide (1c), respectively with 2 mol equiv of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide (2a), 2-azidoethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (2b), and 2-azidoethyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2c), respectively, afforded the corresponding bis-cycloadducts 3-5, containing two 1,2,3-triazole moieties each, in 38-76% yield. Reaction of 1 mol equiv of 2c with 1 mol equiv of le under otherwise identical conditions gave the mono-cycloadduct 6, containing one 1,2,3-triazole and one 2-propynylamide moiety, in 77% yield. Reaction of 6 with 2a afforded 7, containing two different sugar moieties, in 67% yield. (c) 2008 Elsevier Ltd. All rights reserved.