3,4-ethylenedioxythiophene-2,5-di(N-isopropylcarboxamide) | 1276734-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4-ethylenedioxythiophene-2,5-di(N-isopropylcarboxamide)
• 英文别名: 2,5-di(isopropylamide)-3,4-ethylenedioxythiophene；5-N,7-N-di(propan-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxamide
• CAS: 1276734-07-6
• 化学式: C₁₄H₂₀N₂O₄S
• 分子量: 312.39
• InChiKey: MDEFASSHSJEQQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-乙撑二氧基噻吩-2,5-二羧酸 在 氯化亚砜 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 26.5h， 生成 3,4-ethylenedioxythiophene-2,5-di(N-isopropylcarboxamide)
  参考文献：
  名称：

  Axial chirality of N,N′-disubstituted 3,4-ethylenedioxythiophene-2,5-dicarboxamides

  摘要：

  通过3,4-乙撑二氧噻吩-2,5-二甲酰氯与相应的伯胺之间形成酰胺键合成了一系列N,N'-二取代的3,4-乙撑二氧噻吩-2,5-二甲酰胺，其中尺寸和性质取代基不同。通过X射线结构分析确定了所制备化合物的晶体结构。通过DFT计算得到了构象异构体之间相互转化的机理和反应速率。所有研究的化合物都显示出具有分子对称性 C 2 的轴向手性。研究的化合物中酰胺键异构化和二恶烷环的扭曲导致形成一系列构象异构体，其中 s-trans/s-trans 构象异构体在能量上最有利。

  DOI：

  10.1007/s11224-011-9885-x

文献信息

• Conformational disorder of dioxane ring in a crystal of 2,5-di(isopropylamide)-3,4-ethylenedioxythiophene
  作者：Krešimir Molčanov、Ivana Stolić、Goran Kovačević、Biserka Kojić-Prodić、Miroslav Bajić

  DOI：10.1016/j.molstruc.2010.12.011

  日期：2011.2

  The X-ray structure analysis based on high-quality single-crystal data obtained at room temperature and 100 K using a high-intensity Cu K alpha beam produces a molecular structure of the title compound that was in disagreement with IR, H-1 and C-13 NMR data. Vibrations of the double C = C bond lack in IR spectrum whereas signals of two methylene groups are visible in the H NMR spectrum. 13C NMR shows a spectrum of a C-2 or C-s-symmetric compound with a corresponding signal at 65.05 ppm characteristic for saturated carbon atoms in dioxane rings. The two chemically different models can be derived from the results of refinement: (a) model comprising two conformers of dioxane ring, and (b) presence of dioxene ring in which a conformational disorder simulates a Csp(2)-Csp(2) bond. Both models were refined and compared with spectroscopic data that definitely ruled out a presence of dioxene ring. Conformational disorder of dioxane ring in a crystal of 2,5-di(isopropylamide)-3,4-ethylenedioxythiophene simulates Csp(2)-Csp(2) bond disguising the correct molecular structure. Density functional theory, M06-2X/6-311G(d, p), was used to distinguish static from dynamic disorder. (C) 2010 Elsevier B.V. All rights reserved.