5α-cholestan[3,2-b]quinoline | 23455-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5α-cholestan[3,2-b]quinoline
• 英文别名: (3aS,3bR,13S,13bS,15aR)-13a,15a-dimethyl-1-(6-methylheptan-2-yl)-2,3,3a,3b,4,5,5a,6,13,13a,13b,14,15,15a-tetradecahydro-1H-cyclopenta[5,6]naphtho[1,2-b]acridine；5α-cholest-2-eno[3,2-b]quinoline；5α-Cholest-2-eno[3,2-b]chinolin；(1S,14S,15S,18R,19R,22S,23R)-14,18-dimethyl-19-[(2R)-6-methylheptan-2-yl]-4-azahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosa-3,5,7,9,11-pentaene
• CAS: 23455-24-5
• 化学式: C₃₄H₄₉N
• 分子量: 471.77
• InChiKey: JIZWXFQBGPQANX-XSLJFIDMSA-N

物化性质

• 熔点：
  183-186 °C
• 沸点：
  572.6±19.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 氢氧化钾 作用下， 生成 5α-cholestan[3,2-b]quinoline
  参考文献：
  名称：

  Buu-Hoi; Cagniant, Chemische Berichte, 1944, vol. 77/79, p. 121,125

  摘要：

  DOI：

文献信息

• Superbase-Mediated Indirect Friedländer Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
  作者：Rahul P.、Nitha P. R.、Vishnu K. Omanakuttan、Sheba Ann Babu、P. Sasikumar、Vakayil K. Praveen、Henning Hopf、Jubi John

  DOI：10.1002/ejoc.202000365

  日期：2020.5.29

  A transition metal‐free superbase mediated indirect Friedländer reaction was developed for accessing functionalized quinolines using o‐aminobenzyl alcohol and ketones with an active methylene moiety. The reaction was employed in the functionalization of natural products and the applicability of the reaction for gram‐scale synthesis of quinolines was also demonstrated.

  开发了一种不含过渡金属的超碱介导的间接Friedländer反应，可使用邻氨基苯甲醇和具有活性亚甲基的酮来获得官能化的喹啉。该反应被用于天然产物的功能化，并且也证明了该反应在克规模合成喹啉中的适用性。
• 202. Steroids and related compounds. Part XII. Some heterocyclic derivatives
  作者：H. Antaki、V. Petrow

  DOI：10.1039/jr9510000901

  日期：——
• Buu-Hoi; Cagniant, Chemische Berichte, 1944, vol. 77/79, p. 121,125
  作者：Buu-Hoi、Cagniant

  DOI：——

  日期：——
• A microwave promoted solvent-free approach to steroidal quinolines and their in vitro evaluation for antimicrobial activities
  作者：Shyamalee Gogoi、Kommuri Shekarrao、Aparajita Duarah、Tarun C. Bora、Sanjib Gogoi、Romesh C. Boruah

  DOI：10.1016/j.steroids.2012.08.008

  日期：2012.11

  The preparation of A-ring and D-ring fused steroidal quinolines is described from one-pot reaction of steroidal beta-bromovinylaldehydes and arylamines in solvent-free and catalyst-free condition under microwave irradiation. The antimicrobial activities of the compounds were tested by agar diffusion assay and broth macro dilution method. Compounds 7a, 7e and 7g-h showed promising in vitro activity when tested against fungal pathogen Aspergillus niger whereas compounds 7e-h and 7j showed promising activity when tested against fungal pathogen Candida albicans. Compounds 7c and 7f showed potent inhibition against the growth of Gram negative bacteria Pseudomonas aeruginosa and compounds 7e, 7g-h and 7j inhibited the growth of tested Gram positive bacteria Bacillus subtilis and Staphylococcus aureus. (C) 2012 Elsevier Inc. All rights reserved.