(E)-2,3-dihydro-2-(4-methoxyphenylacylidene)-1,3,3-trimethyl-1H-indole | 1276019-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-2,3-dihydro-2-(4-methoxyphenylacylidene)-1,3,3-trimethyl-1H-indole
• 英文别名: (2E)-1-(4-methoxyphenyl)-2-(1,3,3-trimethylindol-2-ylidene)ethanone
• CAS: 1276019-30-7
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: HZKIPDQSEBVKMM-CPNJWEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 、 对甲氧基苯甲酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (E)-2,3-dihydro-2-(4-methoxyphenylacylidene)-1,3,3-trimethyl-1H-indole
  参考文献：
  名称：

  X-ray, DFT, FTIR and NMR structural study of 2,3-dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole

  摘要：

  Fischer base derivatives are widely used as precursor in the formation of different chemical switches. Besides, in the presence of acyl chlorides, indole enaminoketone derivatives can be prepared. 2,3-Dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole, R = 4-NO2, 3,5-(NO2)(2) and 4-OCH3, have been characterized previously but only by H-1 NMR, thus further characterization was performed by FTIR, C-13 NMR and when suitable crystals were obtained by single crystal X-ray diffraction analyses. The structures of the three molecules were additionally analyzed by OFT methods, B3LYP and PW91 functionals, using 6-311G(d,p) basis set. The optimized structures obtained were compared with those determined by crystallographic data. The probable assignments of the anharmonic experimental solid state vibrational frequencies for these molecules have been also made based on the calculated harmonic frequencies in vacuum at the same level of theory for the optimized structures. Correlations between experimental chemical shifts and CIAO calculated magnetic isotropic shielding constants with B3LYP and PW91 functionals using the 6-311++G(3df,3pd) basis set are also reported. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.12.001

文献信息

• X-ray, DFT, FTIR and NMR structural study of 2,3-dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole
  作者：Oscar F. Vázquez-Vuelvas、Julia V. Hernández-Madrigal、Rubén Gaviño、Mikhail A. Tlenkopatchev、David Morales-Morales、Juan M. Germán-Acacio、Zeferino Gomez-Sandoval、Cesar Garcias-Morales、Armando Ariza-Castolo、Armando Pineda-Contreras

  DOI：10.1016/j.molstruc.2010.12.001

  日期：2011.2

  Fischer base derivatives are widely used as precursor in the formation of different chemical switches. Besides, in the presence of acyl chlorides, indole enaminoketone derivatives can be prepared. 2,3-Dihydro-2-(R-phenylacylidene)-1,3,3-trimethyl-1H-indole, R = 4-NO2, 3,5-(NO2)(2) and 4-OCH3, have been characterized previously but only by H-1 NMR, thus further characterization was performed by FTIR, C-13 NMR and when suitable crystals were obtained by single crystal X-ray diffraction analyses. The structures of the three molecules were additionally analyzed by OFT methods, B3LYP and PW91 functionals, using 6-311G(d,p) basis set. The optimized structures obtained were compared with those determined by crystallographic data. The probable assignments of the anharmonic experimental solid state vibrational frequencies for these molecules have been also made based on the calculated harmonic frequencies in vacuum at the same level of theory for the optimized structures. Correlations between experimental chemical shifts and CIAO calculated magnetic isotropic shielding constants with B3LYP and PW91 functionals using the 6-311++G(3df,3pd) basis set are also reported. (C) 2010 Elsevier B.V. All rights reserved.