5'-formyl-4'-hydroxy-3'-methoxybiphenyl-4-carbonitrile | 769971-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5'-formyl-4'-hydroxy-3'-methoxybiphenyl-4-carbonitrile
• 英文别名: 5-(4-cyanophenyl)-2-hydroxy-3-methoxybenzaldehyde；5-(4-cyanophenyl)-3-methoxysalicylaldehyde；5'-Formyl-4'-hydroxy-3'-methoxy-biphenyl-4-carbonitrile；4-(3-formyl-4-hydroxy-5-methoxyphenyl)benzonitrile
• CAS: 769971-97-3
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: ISVHQHTZLBCCCP-UHFFFAOYSA-N

物化性质

• 熔点：
  177-177.5 °C
• 沸点：
  419.9±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-formyl-4'-hydroxy-3'-methoxybiphenyl-4-carbonitrile 以 乙醇 为溶剂， 反应 4.0h， 以68.3%的产率得到N-(5-(4-cyanophenyl)-3-methoxysalicylidene)-phenylene-1,2-diamine
  参考文献：
  名称：

  基于不对称席夫碱配体的第一种异双核 Zn-Ln（Ln = La、Nd、Eu、Gd、Tb、Er 和 Yb）配合物的合成、表征和光物理性质

  摘要：

  摘要 用新型不对称席夫碱锌配合物ZnL(H 2 L = N-(3-甲氧基水杨亚基)-N'-(5-(4-氰基苯基)-3-甲氧基水杨基)亚苯基-1, 2-二胺)，得到以苯-1、2-二胺、3-甲氧基水杨醛和5-(4-氰基苯基)-3-甲氧基水杨醛为前驱体，合成一系列异双核Zn-Ln配合物[ZnLnL(NO 3 ) 3 (CH 3 CN) ] (Ln = La, 1; Ln = Nd, 2; Ln = Eu, 3; Ln = Gd, 4; Ln = Tb, 5; Ln = Er, 6; Ln = Yb, 7) Ln(NO3)3·6H2O。这些配合物的光物理研究表明，由于有效的分子内能量转移，不对称席夫碱配体的激发态已敏化了具有微秒范围发射寿命的强且特征性的 NIR 发光。

  DOI：

  10.1080/00387010.2012.692427
• 作为产物：
  描述：

  2-羟基-5-碘-3-甲氧基苯甲醛 、 4-氰基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 生成 5'-formyl-4'-hydroxy-3'-methoxybiphenyl-4-carbonitrile
  参考文献：
  名称：

  Synthesis and two-photon absorption properties of unsymmetrical metallosalophen complexes

  摘要：

  Several new unsymmetrical metallosalphen complexes derived from the condensation of a monoimine and salicylaldehyde in the presence of a transition metal ion as a template have been synthesized and characterized. Their linear and third-order non-linear optical (NLO) properties have been investigated in detail. With different substituted donor or acceptor groups at the 5-position of the salicylidene fragment, these metallosalophen complexes exhibit slightly different two-photon absorption (TPA) cross-section sigma((2)) values. Theoretical calculations based on density functional theory were also carried out to help with the interpretations of the experimental results. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.09.050

文献信息

• Dicationic triaryl analogs as anti-protozoan agents
  申请人：Boykin W. David

  公开号：US20050148646A1

  公开（公告）日：2005-07-07

  Novel dicationic, heterocyclic triaryl compounds are useful in the treatment of microbial infections, such as Trypanosoma brucei rhodesiense infection and Plasmodium falciparum infection. These compounds are accordingly useful in treating second-stage human African trypanosomiasis. Pharmaceutical formulations comprising these compounds can be used in methods of treating microbial infections.

  新型二元离子、杂环三芳基化合物可用于治疗微生物感染，例如Trypanosoma brucei rhodesiense感染和Plasmodium falciparum感染。因此，这些化合物可用于治疗第二阶段的人类非洲锥虫病。包含这些化合物的药物制剂可用于治疗微生物感染的方法中。
• Dicationic biphenyl benzimidazole derivatives as antiprotozoal agents
  作者：Mohamed A. Ismail、Reto Brun、Tanja Wenzler、Farial A. Tanious、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2004.07.056

  日期：2004.10

  A series of biphenyl benzimidazoles diamidines 6a-i were synthesized from their respective diamidoximes, through the bis-O-acetoxyamidoxime followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. The target compounds contain hydroxy and/or methoxy substituted 1,3-phenyl groups as the central spacer between the two amidino bearing aryl groups. All of the diamidines showed strong DNA affinities as judged by high DeltaT(m) values with poly(dA(.)dT)(2), which varied with structure and is discussed. Seven of the nine new diamidines gave in vitro IC50 values of approximately 30nM or less versus Trypanosoma brucei rhodesiense (T.b.r.). Generally the diamidines were less active versus Plasmodium falciparum (P.f), however one compound exhibited excellent activity with an IC50 value of 2.1 nM. Five of the nine diamidines exhibited excellent in vivo activity in the trypanosomal STIB900 mouse model giving 3/4 or 4/4 cures at dosage of 20mg/kg ip and three showed similar efficacy at dosage of 10mg/kg or lower. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis, Characterization, and Photophysical Properties of First Heterobinuclear Zn-Ln (Ln = La, Nd, Eu, Gd, Tb, Er, and Yb) Complexes Based on Asymmetric Schiff-Base Ligand
  作者：Shunsheng Zhao、Xiangrong Liu、Xingqiang Lü、Wai-kwok Wong

  DOI：10.1080/00387010.2012.692427

  日期：2013.2

  complex ZnL(H 2 L = N-(3-methoxysalicylidene)-N’-(5-(4-cyanophenyl)-3-methoxysalicylidene)phenylene-1, 2-diamine), obtained from phenylene-1, 2-diamine, 3-methoxysalicylaldehyde, and 5-(4-cyanophenyl)-3-methoxysalicylaldehyde, as the precursor, a series of heterobinuclear Zn-Ln complexes [ZnLnL(NO 3 ) 3 (CH 3 CN)] (Ln = La, 1; Ln = Nd, 2; Ln = Eu, 3; Ln = Gd, 4; Ln = Tb, 5; Ln = Er, 6; Ln = Yb, 7) were

  摘要 用新型不对称席夫碱锌配合物ZnL(H 2 L = N-(3-甲氧基水杨亚基)-N'-(5-(4-氰基苯基)-3-甲氧基水杨基)亚苯基-1, 2-二胺)，得到以苯-1、2-二胺、3-甲氧基水杨醛和5-(4-氰基苯基)-3-甲氧基水杨醛为前驱体，合成一系列异双核Zn-Ln配合物[ZnLnL(NO 3 ) 3 (CH 3 CN) ] (Ln = La, 1; Ln = Nd, 2; Ln = Eu, 3; Ln = Gd, 4; Ln = Tb, 5; Ln = Er, 6; Ln = Yb, 7) Ln(NO3)3·6H2O。这些配合物的光物理研究表明，由于有效的分子内能量转移，不对称席夫碱配体的激发态已敏化了具有微秒范围发射寿命的强且特征性的 NIR 发光。
• Synthesis and two-photon absorption properties of unsymmetrical metallosalophen complexes
  作者：Jie Zhang、Cheng Zhong、XunJin Zhu、Hoi-Lam Tam、King-Fai Li、Kok-Wai Cheah、Wai-Yeung Wong、Wai-Kwok Wong、Richard A. Jones

  DOI：10.1016/j.poly.2012.09.050

  日期：2013.1

  Several new unsymmetrical metallosalphen complexes derived from the condensation of a monoimine and salicylaldehyde in the presence of a transition metal ion as a template have been synthesized and characterized. Their linear and third-order non-linear optical (NLO) properties have been investigated in detail. With different substituted donor or acceptor groups at the 5-position of the salicylidene fragment, these metallosalophen complexes exhibit slightly different two-photon absorption (TPA) cross-section sigma((2)) values. Theoretical calculations based on density functional theory were also carried out to help with the interpretations of the experimental results. (c) 2012 Elsevier Ltd. All rights reserved.