[[2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]amino]thiourea | 1228657-81-5

• 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-ylidene]amino]thiourea
• CAS: 1228657-81-5
• 化学式: C₂₁H₂₂F₂N₄S
• 分子量: 400.495
• InChiKey: DJGDPFHBMOQGPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [[2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]amino]thiourea 、 乙酸酐 以90%的产率得到2,4-[bis(m-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-Δ2-1,3,4-thiadiazoline
  参考文献：
  名称：

  2,4-二芳基-3-氮杂双环[3.3.1] nonan-9-ones含氮和硫的螺杂环的高效合成，光谱分析和抗菌研究

  摘要：

  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

  DOI：

  10.1016/j.bmcl.2010.09.021
• 作为产物：
  描述：

  2,4-bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one 、 氨基硫脲 生成 [[2,4-Bis(3-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]amino]thiourea
  参考文献：
  名称：

  Efficient Synthesis of Novel 2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-Δ ²-1,3,4-thiadiazolines

  摘要：

  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.

  DOI：

  10.1080/00397910903161694

文献信息

• 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.
• 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.
• 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.
• 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