2,4-戊二炔-1-基3,5-二羟基苯甲酸酯 | 623176-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-戊二炔-1-基3,5-二羟基苯甲酸酯
• 英文名称: penta-2,4-diynyl 3,5-dihydroxybenzoate
• 英文别名: 3,5-dihydroxybenzoic acid 2,4-pentyldiynyl ester；2,4-Pentadiyn-1-yl 3,5-dihydroxybenzoate
• CAS: 623176-87-4
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: ZHTOYNUOEQRFJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-bis(tert-butyldimethylsilyloxy)benzoic acid 在 吡啶 、 4-二甲氨基吡啶 、 N,N-二甲基丁胺 、 氢氟酸 、 二甲胺基磺酰氯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2,4-戊二炔-1-基3,5-二羟基苯甲酸酯
  参考文献：
  名称：

  Single-Crystal-to-Single-Crystal Topochemical Polymerizations of a Terminal Diacetylene:  Two Remarkable Transformations Give the Same Conjugated Polymer

  摘要：

  Host-guest chemistry was used to prepare a cocrystal of a dipyridyl substituted oxalamide host and a resorcinol derivative of a terminal diacetylene. X-ray crystallography revealed that the molecules assemble into a triple-helix with the diacetylene functionalities aligned in the center of the helix. Upon heating, the diacetylenes polymerize to give the corresponding polymer. In a second experiment, the X-ray structure of the crystalline hydrate of the same diacetylene also showed a suitable alignment of the diacetylene functionalities. These crystals polymerize at only 50 degrees C with the C1 carbon end of the diacetylene undergoing an unprecedented 2.4 A inward swinging movement. This results in a remarkable 9% increase in crystal density. These are the first structurally characterized polymerizations of any terminal diacetylene. A detailed comparison of the two sets of structural changes offers an interesting insight into the precise trajectories of polymerization reactions.

  DOI：

  10.1021/ja037557+

文献信息

• Single-Crystal-to-Single-Crystal Topochemical Polymerizations of a Terminal Diacetylene:  Two Remarkable Transformations Give the Same Conjugated Polymer
  作者：Xi Ouyang、Frank W. Fowler、Joseph W. Lauher

  DOI：10.1021/ja037557+

  日期：2003.10.1

  Host-guest chemistry was used to prepare a cocrystal of a dipyridyl substituted oxalamide host and a resorcinol derivative of a terminal diacetylene. X-ray crystallography revealed that the molecules assemble into a triple-helix with the diacetylene functionalities aligned in the center of the helix. Upon heating, the diacetylenes polymerize to give the corresponding polymer. In a second experiment, the X-ray structure of the crystalline hydrate of the same diacetylene also showed a suitable alignment of the diacetylene functionalities. These crystals polymerize at only 50 degrees C with the C1 carbon end of the diacetylene undergoing an unprecedented 2.4 A inward swinging movement. This results in a remarkable 9% increase in crystal density. These are the first structurally characterized polymerizations of any terminal diacetylene. A detailed comparison of the two sets of structural changes offers an interesting insight into the precise trajectories of polymerization reactions.