(2R)-1-(4-fluorophenyl)-2-(oxan-2-yloxy)propan-1-one | 917246-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-1-(4-fluorophenyl)-2-(oxan-2-yloxy)propan-1-one
• CAS: 917246-39-0
• 化学式: C₁₄H₁₇FO₃
• 分子量: 252.286
• InChiKey: CHDNEKBQRPYCDH-VUUHIHSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲基二甲基异丙氧基硅烷 、 (2R)-1-(4-fluorophenyl)-2-(oxan-2-yloxy)propan-1-one 在 magnesium 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 生成 (2S,3R)-2-(4-fluorophenyl)-1-(isopropoxydimethylsilyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)butan-2-ol
  参考文献：
  名称：

  Substituent effect of fluorine atoms in the 2,4-difluorophenyl group on antifungal activity of CS-758

  摘要：

  CS-758 is a novel triazole antifungal agent. To ascertain the effect of the fluorine atoms in the 2,4-difluorophenyl group, a series of compounds, 12a-12d, which have fluorine atom(s) in different positions on the benzene ring, were synthesized, and the minimum inhibitory concentrations (MICs) of this series of compounds were determined. All the compounds, including CS-758, exhibited excellent MICs against Candida, Aspergillus, and Cryptococcus species. Among them, the compounds having a fluorine atom in the 2-position on the benzene ring (12a, 12c, 12d, and CS-758) showed stronger antifungal activity particularly against Aspergillus species. The MICs of these compounds surpassed those of fluconazole and itraconazole against Candida, Aspergillus, and Cryptococcus species. (C) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.008
• 作为产物：
  描述：

  (2R)-4-(2-(四氢吡喃-2-基)-羟基丙酰基)吗啉 、 对溴氟苯 在 magnesium 作用下， 生成 (2R)-1-(4-fluorophenyl)-2-(oxan-2-yloxy)propan-1-one
  参考文献：
  名称：

  光学活性抗真菌唑类。IV。（2R，3R）-3-偶氮基-2-（取代的苯基）-1-（1H-1,2,4-三唑-1-基）-2-丁醇的合成及抗真菌活性。

  摘要：

  （2R，3R）-3-偶氮基-2-（取代的苯基）-1-（1H-1,2,4-三唑-1-基）-2-丁醇（III）由（2R，3S）-制备。 3-甲基-2-（取代的苯基）-2-（1H-1,2,4-三唑-1-基）甲基环氧乙烷（21a-f）与1H-1,2,3-三唑的开环反应和1H-四唑，并在体外和体内评估了对白色念珠菌的抗真菌活性。由1-[（2R）-2-（3,4,5,6-四氢-2H-吡喃-2-基）氧基丙酰基合成了关键的光学中间体环氧乙烷（21a-f）吗啡酮e（24）和取代的苯基溴化镁（23）通过六个步骤以立体控制方式进行。3-（1H-1,2,3，-三唑-1-基）-（IIIa）和3-（2H-2-四唑基）-2-丁醇（IIId）衍生物对小鼠念珠菌病具有很强的保护作用。

  DOI：

  10.1248/cpb.43.432

文献信息

• Substituent effect of fluorine atoms in the 2,4-difluorophenyl group on antifungal activity of CS-758
  作者：Yoshiko Kagoshima、Toshiyuki Konosu

  DOI：10.1016/j.jfluchem.2005.12.008

  日期：2006.5

  CS-758 is a novel triazole antifungal agent. To ascertain the effect of the fluorine atoms in the 2,4-difluorophenyl group, a series of compounds, 12a-12d, which have fluorine atom(s) in different positions on the benzene ring, were synthesized, and the minimum inhibitory concentrations (MICs) of this series of compounds were determined. All the compounds, including CS-758, exhibited excellent MICs against Candida, Aspergillus, and Cryptococcus species. Among them, the compounds having a fluorine atom in the 2-position on the benzene ring (12a, 12c, 12d, and CS-758) showed stronger antifungal activity particularly against Aspergillus species. The MICs of these compounds surpassed those of fluconazole and itraconazole against Candida, Aspergillus, and Cryptococcus species. (C) 2005 Elsevier B.V. All rights reserved.
• Optically Active Antifungal Azoles. IV. Synthesis and Antifungal Activity of (2R,3R)-3-Azolyl-2-(substituted phenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanols.
  作者：Akihiro TASAKA、Norikazu TAMURA、Yoshihiro MATSUSHITA、Tomoyuki KITAZAKI、Ryogo HAYASHI、Kenji OKONOGI、Katsumi ITOH

  DOI：10.1248/cpb.43.432

  日期：——

  3S)-3-methyl-2-(substituted phenyl)-2-(1H-1,2,4-triazol-1-yl)methyloxiranes (21a-f) by a ring-opening reaction with 1H-1,2,3-triazole and 1H-tetrazole and evaluated for antifungal activity against Candida albicans in vitro and in vivo. The optically active oxiranes (21a--f) which serve as the key synthetic intermediates, were synthesized from 1-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxypropanoyl]morpholin e (24)

  （2R，3R）-3-偶氮基-2-（取代的苯基）-1-（1H-1,2,4-三唑-1-基）-2-丁醇（III）由（2R，3S）-制备。 3-甲基-2-（取代的苯基）-2-（1H-1,2,4-三唑-1-基）甲基环氧乙烷（21a-f）与1H-1,2,3-三唑的开环反应和1H-四唑，并在体外和体内评估了对白色念珠菌的抗真菌活性。由1-[（2R）-2-（3,4,5,6-四氢-2H-吡喃-2-基）氧基丙酰基合成了关键的光学中间体环氧乙烷（21a-f）吗啡酮e（24）和取代的苯基溴化镁（23）通过六个步骤以立体控制方式进行。3-（1H-1,2,3，-三唑-1-基）-（IIIa）和3-（2H-2-四唑基）-2-丁醇（IIId）衍生物对小鼠念珠菌病具有很强的保护作用。