4-(6-((6-((6-((6-((6-((6-iodo-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)-2-methylbut-3-yn-2-ol | 1378991-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(6-((6-((6-((6-((6-((6-iodo-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)-2-methylbut-3-yn-2-ol
• CAS: 1378991-19-5
• 化学式: C₉₃H₁₂₁IN₆O₇
• 分子量: 1561.92
• InChiKey: DGRKPTDXHPXHGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.22
• 重原子数：
  107.0
• 可旋转键数：
  48.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  152.95
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-(6-((6-((6-((6-((6-((6-iodo-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)-2-methylbut-3-yn-2-ol 、 1-(trimethylsilyl)-1,7-octadiyne 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以71%的产率得到
  参考文献：
  名称：

  Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

  摘要：

  Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.069
• 作为产物：
  描述：

  6,6'-((4-(octyloxy)pyridine-2,6-diyl)bis(ethyne-2,1-diyl))bis(2-iodo-4-(octyloxy)pyridine) 、 4-(6-((6-((6-ethynyl-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)-2-methylbut-3-yn-2-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到4-(6-((6-((6-((6-((6-((6-iodo-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)ethynyl)-4-(octyloxy)pyridin-2-yl)-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

  摘要：

  Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.069

文献信息

• IMPROVEMENT OF HELIX-FORMING ABILITY OF MANNOSIDE-LINKED ETHYNYLPYRIDINE OLIGOMERS CONSTRUCTED BY CONVERGENT SYNTHESIS
  作者：Masahiko Inouye、Hajime Abe、Hiroki Makida

  DOI：10.3987/com-12-s(n)97

  日期：——

  The improvement of helix-forming ability of a-D-mannoside-linked 2,6-pyridylene ethynylene "ethynylpyridine" oligomers was made by modification of the linker between the ethynylpyridine and mannoside moieties in the oligomers. The linker involves a triazole ring because the preparation utilizes Huisgen reaction, and the proper distance between the triazole ring and the ethynylpyridine moiety was found to be important to show strong Cotton effects. Dedicated to Professor Ei-ichi Negishi on the occasion of his 77th birthday