5-(2-(N,N-Dimethylamino)ethoxy)-7H-benzo(c)fluorene | 83439-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5-(2-(N,N-Dimethylamino)ethoxy)-7H-benzo(c)fluorene
• 英文别名: 2-(7H-benzo[c]fluoren-5-yloxy)-N,N-dimethylethanamine
• CAS: 83439-22-9
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: BESCVFOMHYNCAU-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C(Solv: chloroform (67-66-3))
• 沸点：
  486.4±38.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-(2-dimethylaminoethoxy)-7-oxo-7H-benzofluorene 以65%的产率得到
  参考文献：
  名称：

  KREPELKA, J.;VANCUROVA, I.;HOLUBEK, J.;MELKA, M.;REZABEK, K., COLLECT. CZECH. CHEM. COMMUN., 1982, 47, N 7, 1856-1866

  摘要：

  DOI：

文献信息

• Derivatives of benzo(c)fluorene: II. Synthesis and biological effect of basic ethers of 7-oxo-7H-benzo(c)fluorene
  作者：Jiří Křepelka、Iva Vančurová、Jiří Holubek、Milan Mělka、Karel Řežábek

  DOI：10.1135/cccc19821856

  日期：——

  Alkylation of phenols IIa-IIc with ω-(N,N-dialkylamino)alkyl chlorides IIIa-IIId in an aqueous and/or a two-phase (toluene and aqueous potassium hydroxide) medium, and reactions of phenols IId-IIf with isopropylamine, gave rise to ethers IV-XIX. Compounds IV and V were used to prepare derivatives XX-XXVI. Reduction of the 7-oxo group in the compound V by the action of sodium borohydride produced the 7-hydroxy derivatives XXIV-XXVI, whereas reduction under conditions of the Wolf-Kishner reaction led to derivatives XXVII and XXVIII, respectively, which were also obtained by alkylation of XXIX with IIIa in an anhydrous medium. The compound XXIX was prepared by reduction of compound IIa. Most the of compounds prepared had marked antineoplastic effects, particularly compounds IV and V. Compounds V, VII, IX and XVIII exhibited antibacterial effects, and compounds XVI, XVIII and XXIII were as efficacious in subcutaneous application against encephalomyocarditis virus as Tiloron, used as standard.

  将酚类化合物IIa-IIc与ω-(N,N-二烷基氨基)烷基氯化物IIIa-IIId在水性和/或两相（甲苯和水性氢氧化钾）介质中进行烷基化反应，以及酚类化合物IId-IIf与异丙胺的反应，产生了醚类化合物IV-XIX。化合物IV和V用于制备衍生物XX-XXVI。通过钠硼氢化物还原化合物V中的7-酮基团产生7-羟基衍生物XXIV-XXVI，而在Wolf-Kishner反应条件下还原则产生衍生物XXVII和XXVIII，这两者也可通过在无水介质中用IIIa对XXIX进行烷基化而获得。化合物XXIX是通过还原化合物IIa制备的。大多数制备的化合物具有显著的抗肿瘤效果，尤其是化合物IV和V。化合物V、VII、IX和XVIII表现出抗菌效果，而化合物XVI、XVIII和XXIII在皮下应用对脑心肌炎病毒的效果与用作标准的Tiloron一样有效。