(2E,5E)-2,5-bis((1H-pyrrol-2-yl)methylene)cyclopentanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2E,5E)-2,5-bis((1H-pyrrol-2-yl)methylene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(1H-pyrrol-2-ylmethylidene)cyclopentan-1-one
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: ZXCMCPINSJLVEY-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.6
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,5E)-2,5-bis((1H-pyrrol-2-yl)methylene)cyclopentanone 以 氘代二甲亚砜 为溶剂， 生成 (2Z,5E)-2,5-bis((1H-pyrrol-2-yl)methylene)cyclopentanone
  参考文献：
  名称：

  Molecular Structure and Photoinduced Intramolecular Hydrogen Bonding in 2-Pyrrolylmethylidene Cycloalkanones

  摘要：

  The structures of pyrrolylmethylidene derivatives of 2,3-dihydro-1H-inden-1-one (3), 3,4-dihydro-naphthalen-1(2H)-one (4), and cycloalkanones (5-7) were studied for the first time in the solid state and solution by NMR, IR, and UV spectroscopies supported by DFT quantum mechanical calculations. It was shown that all studied compounds except cycloheptanone derivative 7 both in crystal and in solution exist in the form of dimers where single E or E,E configuration with respect to the exocyclic C=C bond is stabilized by intermolecular hydrogen bonds N-H center dot center dot center dot O=C. UV irradiation at a wavelength of 365 nm of MeCN or DMSO solutions of 3-6 results, depending on the exposition time and solvent, partial to complete isomerization to the Z or Z,E isomers (in the case of 6, also the Z,Z isomer). The NMR and IR spectroscopy data show the existence of a strong intramolecular hydrogen bond N-H center dot center dot center dot O=C in the Z moieties of isomerized compounds. The studied compounds are protonated by trifluoroacetic acid at the carbonyl oxygen, in spite of the reverse order of basicity and nucleophilicity of the carbonyl group and the pyrrole ring. Investigation of the behavior of compound 6 with respect to acetate and fluoride anions allows one to consider it as a potential fluoride sensor.

  DOI：

  10.1021/acs.joc.5b01604
• 作为产物：
  描述：

  2-吡咯甲醛 、 环戊酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以90%的产率得到(2E,5E)-2,5-bis((1H-pyrrol-2-yl)methylene)cyclopentanone
  参考文献：
  名称：

  Molecular Structure and Photoinduced Intramolecular Hydrogen Bonding in 2-Pyrrolylmethylidene Cycloalkanones

  摘要：

  The structures of pyrrolylmethylidene derivatives of 2,3-dihydro-1H-inden-1-one (3), 3,4-dihydro-naphthalen-1(2H)-one (4), and cycloalkanones (5-7) were studied for the first time in the solid state and solution by NMR, IR, and UV spectroscopies supported by DFT quantum mechanical calculations. It was shown that all studied compounds except cycloheptanone derivative 7 both in crystal and in solution exist in the form of dimers where single E or E,E configuration with respect to the exocyclic C=C bond is stabilized by intermolecular hydrogen bonds N-H center dot center dot center dot O=C. UV irradiation at a wavelength of 365 nm of MeCN or DMSO solutions of 3-6 results, depending on the exposition time and solvent, partial to complete isomerization to the Z or Z,E isomers (in the case of 6, also the Z,Z isomer). The NMR and IR spectroscopy data show the existence of a strong intramolecular hydrogen bond N-H center dot center dot center dot O=C in the Z moieties of isomerized compounds. The studied compounds are protonated by trifluoroacetic acid at the carbonyl oxygen, in spite of the reverse order of basicity and nucleophilicity of the carbonyl group and the pyrrole ring. Investigation of the behavior of compound 6 with respect to acetate and fluoride anions allows one to consider it as a potential fluoride sensor.

  DOI：

  10.1021/acs.joc.5b01604

文献信息

• Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones
  作者：Saulo F.P. Braga、Érika V.P. Alves、Rafaela S. Ferreira、Jordana R.B. Fradico、Paula S. Lage、Mariana C. Duarte、Tatiana G. Ribeiro、Policarpo A.S. Júnior、Alvaro J. Romanha、Maiko L. Tonini、Mário Steindel、Eduardo F. Coelho、Renata B. de Oliveira

  DOI：10.1016/j.ejmech.2013.11.011

  日期：2014.1

  A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 mu M. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 mu M). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (<= 1.2 mu M) with an adequate SI (>= 19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Molecular Structure and Photoinduced Intramolecular Hydrogen Bonding in 2-Pyrrolylmethylidene Cycloalkanones
  作者：Mark Sigalov、Bagrat Shainyan、Nina Chipanina、Larisa Oznobikhina、Natalia Strashnikova、Irina Sterkhova

  DOI：10.1021/acs.joc.5b01604

  日期：2015.11.6

  The structures of pyrrolylmethylidene derivatives of 2,3-dihydro-1H-inden-1-one (3), 3,4-dihydro-naphthalen-1(2H)-one (4), and cycloalkanones (5-7) were studied for the first time in the solid state and solution by NMR, IR, and UV spectroscopies supported by DFT quantum mechanical calculations. It was shown that all studied compounds except cycloheptanone derivative 7 both in crystal and in solution exist in the form of dimers where single E or E,E configuration with respect to the exocyclic C=C bond is stabilized by intermolecular hydrogen bonds N-H center dot center dot center dot O=C. UV irradiation at a wavelength of 365 nm of MeCN or DMSO solutions of 3-6 results, depending on the exposition time and solvent, partial to complete isomerization to the Z or Z,E isomers (in the case of 6, also the Z,Z isomer). The NMR and IR spectroscopy data show the existence of a strong intramolecular hydrogen bond N-H center dot center dot center dot O=C in the Z moieties of isomerized compounds. The studied compounds are protonated by trifluoroacetic acid at the carbonyl oxygen, in spite of the reverse order of basicity and nucleophilicity of the carbonyl group and the pyrrole ring. Investigation of the behavior of compound 6 with respect to acetate and fluoride anions allows one to consider it as a potential fluoride sensor.