6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol | 1415126-46-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol
• 英文别名: 2-methyl-6-(N-phenylanilino)hexa-3,5-diyn-2-ol
• CAS: 1415126-46-3
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: BUFIHJOFRFWPKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酰二苯胺 在 正丁基锂 、 四甲基乙二胺 、 五氯化磷 、 氧气 、 copper(l) chloride 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol
  参考文献：
  名称：

  Preparations, crystal structures and DFT calculations of novel diacetylenes incorporating ynamine moieties

  摘要：

  Two diacetylene molecules incorporating an ynamine moiety, 5-(diphenylamino)-2,4-pentadiyne-1-ol (1) and 6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol (2), were prepared and characterized by single crystal X-ray diffraction, H-1 and C-13 NMR. The crystal structures of 1 and 2 were solved successfully and were interpreted to be controlled mainly by the intermolecular hydrogen-bondings. The difference in the crystal structures between 1 and 2 was well explained by consideration of the steric repulsion with the methyl groups connected to the carbon atom adjacent to the hydroxyl group in 2. The steric effects of the methyl groups on intra and intercolumnar interaction were found to be important for designing molecular and crystal structures of diacetylene molecules. Although the geometries obtained by DFT calculations showed a good agreement on 2 except for the butadiynyl part, a significant difference was recognized at the environment around the nitrogen of 1. The difference could be explained by the effect of the crystal packing. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.003

文献信息

• Preparations, crystal structures and DFT calculations of novel diacetylenes incorporating ynamine moieties
  作者：Yui Tokutome、Natsuki Kubo、Tsunehisa Okuno

  DOI：10.1016/j.molstruc.2012.07.003

  日期：2012.12

  Two diacetylene molecules incorporating an ynamine moiety, 5-(diphenylamino)-2,4-pentadiyne-1-ol (1) and 6-(diphenylamino)-2-methylhexa-3,5-diyn-2-ol (2), were prepared and characterized by single crystal X-ray diffraction, H-1 and C-13 NMR. The crystal structures of 1 and 2 were solved successfully and were interpreted to be controlled mainly by the intermolecular hydrogen-bondings. The difference in the crystal structures between 1 and 2 was well explained by consideration of the steric repulsion with the methyl groups connected to the carbon atom adjacent to the hydroxyl group in 2. The steric effects of the methyl groups on intra and intercolumnar interaction were found to be important for designing molecular and crystal structures of diacetylene molecules. Although the geometries obtained by DFT calculations showed a good agreement on 2 except for the butadiynyl part, a significant difference was recognized at the environment around the nitrogen of 1. The difference could be explained by the effect of the crystal packing. (C) 2012 Elsevier B.V. All rights reserved.