2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one | 1240952-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
• 英文别名: 2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
• CAS: 1240952-24-2
• 化学式: C₂₀H₁₉F₂NO
• 分子量: 327.374
• InChiKey: HIGXCFNMXOBSCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one 在 盐酸羟胺 、 sodium acetate trihydrate 作用下， 以 乙醇 为溶剂， 以86%的产率得到2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one oxime
  参考文献：
  名称：

  新的2,4-二芳基-3-氮杂双环[3.3.1]壬南-9-一肟衍生物的合成，完整的NMR光谱分配和抗真菌筛选

  摘要：

  摘要合成了一系列不同取代的2,4-二芳基-3-氮杂双环[3.3.1]壬南-9-肟，并使用H，H-COSY，NOESY明确分配了它们的1 H和13 C NMR化学位移，HSQC和HMBC光谱数据。根据NMR研究，无论取代基的性质和位置如何，所有报道的化合物均以双椅构型存在，且3-氮杂双环壬烷部分的C-2和C-4处的苯基呈赤道排列。在合成的肟衍生物中，在苯基的邻位/对位带有卤素取代基的化合物对所有测试的生物均显示出良好的抗真菌特性。 图形概要

  DOI：

  10.1007/s00706-009-0221-8
• 作为产物：
  描述：

  环己酮 、 3-氟苯甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以43%的产率得到2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one
  参考文献：
  名称：

  新型2,4-二芳基-3-氮杂双环[3.3.1] nonan-9-one 4'-苯基硫代半咔唑的合成及抗菌研究。

  摘要：

  从相应的2,4-二芳基-3-氮杂双环[3.3.1]获得了新的2,4-二芳基-3-氮杂双环[3.3.1]壬南-9-一4'-苯基硫代半咔唑酮（化合物9-16）。 ] nonan-9-ones。合成的化合物已通过其元素，分析和光谱研究进行了表征。此外，还对这些报道的化合物针对各种微生物的抗菌和抗真菌活性进行了筛选。这些研究证明，针对细菌，针对枯草芽孢杆菌的化合物10和11，针对伤寒沙门氏菌的化合物13，在低浓度（6.25μg/ mL）时显示最大的抑制效力，而对于真菌，化合物11、13和16对白色念珠菌和化合物12和13对抗新型隐球菌，在最小浓度（6.25μg/ mL）下显示出有益的抗真菌活性。

  DOI：

  10.3109/14756366.2010.525508

文献信息

• Efficient synthesis, spectral analysis and antimicrobial studies of nitrogen and sulfur containing spiro heterocycles from 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones
  作者：M. Rani、R. Ramachandran、S. Kabilan

  DOI：10.1016/j.bmcl.2010.09.021

  日期：2010.11

  cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a–2h, 3a and 3b) with acetic anhydride/propionic anhydride and were characterized by Elemental analysis, IR, 1H NMR and 13C NMR spectral analysis. Single crystal X-ray diffraction has also been recorded for compounds 4c and 5a. From the NMR and Single crystal X-ray diffraction analysis, compounds 4b–4d, 4f–4h, 5b, 5c, 5f–5h, 6a

  乙酰基和丙酰基取代的噻二唑衍生物（4a - 4h，5a - 5h，6a，6b，7a和7b）是通过2，4-二芳基-3-氮杂双环[3.3.1] nonan-9-one的环化反应合成的硫代半氨基甲酮（2a – 2h，3a和3b）与乙酸酐/丙酸酐的混合物，并通过元素分析，IR，1 H NMR和13 C NMR光谱进行了表征。还记录了化合物4c和5a的单晶X射线衍射。通过NMR和单晶X射线衍射分析，发现化合物4b - 4d，4f - 4h，5b，5c，5f - 5h，6a，7a和7b采用双椅构型，而化合物4a，4e，5a，5d，5e和6b分别采用环己烷和哌啶环的椅子和船形。此外，使用系列稀释法筛选合成的化合物的抗菌和抗真菌活性。微生物学分析表明，基于氮杂双环壬烷的噻二唑4c / 4h和5c / 5h的C-2和C-4的吸电子功能取代了苯基，对伤寒沙门氏菌，大肠杆菌，肺炎克雷伯菌，黄曲霉，黑曲霉具有显着的抗菌活性。和白色念珠菌的MIC为6
• Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents
  作者：R. Ramachandran、M. Rani、S. Kabilan

  DOI：10.1016/j.bmcl.2009.03.093

  日期：2009.5

  New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (9-16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (1-8) upon cyclization with ethylbromoacetate in the presence of sodium acetate-acetic acid buffer afforded novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene) hydrazono]-1,3-thiazolidin-4-ones (17-24). The synthesized compounds have been characterized by their elemental, analytical and spectral studies. Besides, the reported compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 11/18/20/23 against Staphylococcus aureus, 19/20/24 against Salmonella typhi show maximum inhibition potency at low concentration (6.25 mu g/ml) whereas 18/19 against Candida albicans and 19/20/21 against Rhizopus sp. showed beneficial antifungal activity at minimum concentration. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Novel 2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-<font>Δ</font> ²-1,3,4-thiadiazolines
  作者：M. Rani、R. Ramachandran、S. Kabilan

  DOI：10.1080/00397910903161694

  日期：2010.5.11

  2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-2-1,3,4-thiadiazoline derivatives (3a-h) have been synthesized by the cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a-h) under acetylating condition. The synthesized compounds were characterized by analytical and spectral (infrared, 1H NMR, and 13C NMR) studies.
• Synthesis, structure and conformational analysis of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones and semicarbazones
  作者：R. Ramachandran、M. Rani、S. Kabilan

  DOI：10.1016/j.molstruc.2010.02.005

  日期：2010.4

  A series of thiosemicarbazones and semicarbazones have been synthesized and characterized by one and two dimensional NMR spectroscopy. The possible ring conformations of both the hydrazones are discussed. The chemical shifts and coupling constants suggest that the reported hydrazones adopt twin-chair conformations with equatorial orientation of the aryl substituents. Besides, the proposed conformations are further confirmed by single crystal X-ray diffraction analysis and molecular optimization geometry method. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.
• Synthesis, complete NMR spectral assignments, and antifungal screening of new 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oxime derivatives
  作者：Paramasivam Parthiban、Paramasivam Rathika、Keun Soo Park、Yeon Tae Jeong

  DOI：10.1007/s00706-009-0221-8

  日期：2010.1

  AbstractA series of differently substituted 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oximes have been synthesized and their 1H and 13C NMR chemical shifts have been unambiguously assigned using H,H-COSY, NOESY, HSQC, and HMBC spectral data. On the basis of the NMR studies, irrespective of the nature and position of the substituents, all reported compounds exist in twin-chair conformation with equatorial

  摘要合成了一系列不同取代的2,4-二芳基-3-氮杂双环[3.3.1]壬南-9-肟，并使用H，H-COSY，NOESY明确分配了它们的1 H和13 C NMR化学位移，HSQC和HMBC光谱数据。根据NMR研究，无论取代基的性质和位置如何，所有报道的化合物均以双椅构型存在，且3-氮杂双环壬烷部分的C-2和C-4处的苯基呈赤道排列。在合成的肟衍生物中，在苯基的邻位/对位带有卤素取代基的化合物对所有测试的生物均显示出良好的抗真菌特性。 图形概要