4-[苯基(2-噻吩基)甲基]苯酚 | 731-50-0

• 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: 4-[苯基(2-噻吩基)甲基]苯酚
• 英文名称: (4-hydroxyphenyl)-phenyl-(2-thienyl)methane
• 英文别名: 4-(phenyl-thiophen-2-yl-methyl)-phenol；<4-Hydroxy-phenyl>-phenyl-<2>thienyl-methan；4-[Phenyl(thiophen-2-yl)methyl]phenol
• CAS: 731-50-0
• 化学式: C₁₇H₁₄OS
• 分子量: 266.364
• InChiKey: AMBISNSFKQKTAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[苯基(2-噻吩基)甲基]苯酚 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以72.8%的产率得到diethyl-{2-[4-(phenyl-thiophen-2-yl-methyl)-phenoxy]-ethyl}-amine
  参考文献：
  名称：

  Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis

  摘要：

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-{4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.036
• 作为产物：
  描述：

  2-噻吩甲醛 在 硫酸 、 magnesium 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 4-[苯基(2-噻吩基)甲基]苯酚
  参考文献：
  名称：

  Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis

  摘要：

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-{4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.036

文献信息

• Photoreaction between 2-Benzoylthiophene and Phenol or Indole
  作者：Julia Pérez-Prieto、Francisco Boscá、Raquel E. Galian、Agustín Lahoz、Luis R. Domingo、Miguel A. Miranda

  DOI：10.1021/jo034225e

  日期：2003.6.1

  Laser flash photolysis, density functional theory (DFT) calculations, and product studies have been performed to understand the mechanism of photoreduction of 2-benzoylthiophene (BT) in the presence of phenol or indole. Time-resolved experiments showed that BT ketyl (BTH) and phenoxy (PhO) or indolyl (In) radicals are generated with high rate constants and quantum yields close to 1. However, low conversions (specially in the case of indole) of the starting reagents are obtained upon prolonged lamp irradiation, indicating that recombination within the radical pairs must occur to a large extent, regenerating the starting materials. The solvent-dependence of the quenching rate constants, together with DFT theoretical studies, indicate fundamental differences between the mechanisms of the reaction of BT triplet with phenol and indole. Thus, data for phenol agree with the involvement of a hydrogen-bonded exciplex BT HOPh, where concerted electron and proton transfer leads to the (BTHOPh)-O-... radical pair. However, in the case of indole, electron transfer at the (BTHIn)-H-... stage precedes proton transfer. Finally, C-C cross-coupling products have been isolated and characterized in the preparative irradiation of BT in the presence of phenol and indole. The structures of the products have been confirmed by alternative synthesis.