N-propyl-5-bromosalicylideneimine | 61131-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-propyl-5-bromosalicylideneimine
• 英文别名: 4-Bromo-6-[(propylamino)methylidene]cyclohexa-2,4-dien-1-one；4-bromo-2-(propyliminomethyl)phenol
• CAS: 61131-71-3
• 化学式: C₁₀H₁₂BrNO
• 分子量: 242.115
• InChiKey: PLWPCHJCBBIPHK-UHFFFAOYSA-N

物化性质

• 沸点：
  319.6±32.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-propyl-5-bromosalicylideneimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以1.48 g的产率得到4-bromo-2-[(propylamino)methyl]phenol
  参考文献：
  名称：

  Intermolecular Interactions in the Solid State of Ionic Secondary Mannich Bases

  摘要：

  Two new secondary Mannich bases, 4-bromo-2-[(aminopropyl)methyl]-phenol (1) and 4-nitro-2-[(aminopropyl)methyll-phenol (2), were synthesized. Crystal structures were determined at liquid nitrogen temperature. It was found that in both compounds the proton transfer forms exist in the solid state. In the case of 1, this was unexpected, because of the weak acidity of p-bromophenol being the parent component of this Mannich base. The reason for that was found to be the formation of the O-center dot center dot center dot H-N+ hydrogen bonded tetramer in the solid state. Two cyclic aggregates R-4(2)(8) and R-2(2)(12) describe the pattern of hydrogen bonded interactions in the crystals of both compounds. Additionally, C-H center dot center dot center dot pi interactions stabilize the crystal structures. The hydrogen bonds in I are slightly stronger (N center dot center dot center dot O distances 2.708 and 2.733 angstrom) than in 2 (2.721 and 2.765 angstrom, respectively) despite the fact that p-nitrophenol participating in 2 is a stronger acid. The influence of permittivity of surroundings and the hydrogen bonding pattern on the properties of intermolecular hydrogen bonds are discussed on the basis of B3LYP and MP2 calculations with basis sets 6-31+G(d,p) and 6-31++G(2d,2p). The coupling between hydrogen bonds in crystals was studied with the application of the IR spectra of isotopically diluted species. It was found that such a coupling is stronger for 2, forming weaker hydrogen bonds. Both the theory of IR spectra and quantum chemical calculations demonstrate that the source of the observed behavior is electronic participation in vibronic absorption.

  DOI：

  10.1021/cg201179x
• 作为产物：
  描述：

  正丙胺 、 5-溴水杨醛 以 乙醇 为溶剂， 生成 N-propyl-5-bromosalicylideneimine
  参考文献：
  名称：

  肿瘤选择性 Ru(III) 希夫碱复合物对顺铂耐药 MDA-MB-231 乳腺癌细胞具有强体外活性

  摘要：

  新型钌(III)络合物，通式为Na[RuCl 2 (L 1−3 -N,O) 2 ]，其中L (1–3)表示衍生自5-取代水杨醛的去质子化席夫碱(HL 1 -HL 3 )，烷基胺（丙胺或丁胺）的制备和表征基于元素分析、质谱、红外、电子自旋/顺磁共振（ESR/EPR）光谱和循环伏安研究。通过DFT计算对配合物C1的5种异构体进行了优化。通过电子光谱和荧光猝灭研究了C1 – C3复合物与 DNA（脱氧核糖核酸）和 BSA（牛血清白蛋白）的相互作用。在一组四种人类癌细胞系（K562、A549、EA.hy926、MDA-MB-231）和一种人类非肿瘤细胞系（MRC-5）中研究了C1 – C3的细胞毒活性。复合物表现出明显的细胞选择性特征，IC 50值在 1.6 ± 0.3 至 23.0 ± 0.1 µM 的低微摩尔范围内。顺铂耐药的三阴性乳腺癌细胞MDA-MB-231对复合物表现出最高的敏感性，其中

  DOI：

  10.1007/s00775-023-01989-0