(2R)-2'-fluoro-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone | 204583-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2'-fluoro-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone
• 英文别名: (2R)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone；(2R)-1-(2-fluorophenyl)-2-(oxan-2-yloxy)propan-1-one
• CAS: 204583-33-5
• 化学式: C₁₄H₁₇FO₃
• 分子量: 252.286
• InChiKey: SAWCDFQDHVBROE-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)-2'-fluoro-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 在 magnesium 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 生成 (2S,3R)-2-(2-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：

  邻溴氟苯 、 (2R)-4-(2-(四氢吡喃-2-基)-羟基丙酰基)吗啉 在 溴化乙啶 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以66%的产率得到(2R)-2'-fluoro-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone
  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

• Optically active tetrazole compounds, and fungicidal compositions thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05371100A1

  公开（公告）日：1994-12-06

  An optically active azole compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R.sup.3 is a hydrogen atom or an acyl group; Q is CH or N; --NA is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R.sup.1 and R.sup.2 is an optionally substituted nitrogen-containing heterocyclic group when --NA is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.

  化合物(I)是一种具有光学活性的唑类化合物，其化学式为：##STR1## 其中，R.sup.1和R.sup.2独立地表示氢原子、卤素原子、卤代烷基、卤代氧基或可选地取代的含氮杂环基团；R.sup.3表示氢原子或酰基基团；Q表示CH或N；--NA表示至少具有两个相邻氮原子作为环构成原子的含氮芳香五元杂环基团，其可以被取代，或者是具有两个或更多氮原子作为环构成原子的芳香并环杂环基团，其可以被取代；(R)表示标有(R)的碳原子具有R-构型；但当--NA为1H-1,2,4-三唑-1-基团时，R.sup.1和R.sup.2中的任意一个可以是可选地取代的含氮杂环基团。该化合物或其盐可用作抗真菌剂。
• Optically active azole compounds and their production
  申请人：Takeda Chemical Industries Ltd.

  公开号：US05495024A1

  公开（公告）日：1996-02-27

  An optically active azole compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R.sup.3 is a hydrogen atom or an acyl group; Q is CH or N; ##STR2## is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R.sup.1 and R.sup.2 is an optionally substituted nitrogen-containing heterocyclic group when ##STR3## is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.

  式(I)的光学活性唑类化合物：##STR1## 其中，R.sup.1和R.sup.2独立地为氢原子、卤素原子、卤代烷基、卤代氧基或可选地取代的含氮杂环基团；R.sup.3为氢原子或酰基基团；Q为CH或N; ##STR2## 为至少具有两个相邻氮原子作为环构成原子的含氮芳香五元杂环基团，其可以被取代，或具有两个或更多氮原子作为环构成原子的芳香并环杂环基团，其可以被取代；(R)表示标记有(R)的碳原子具有R-构型；前提是，当##STR3##为1H-1,2,4-三唑-1-基团时，R.sup.1和R.sup.2中的任一种是可选地取代的含氮杂环基团，或其盐，作为抗真菌剂有用。
• Optically active azole compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0548553A1

  公开（公告）日：1993-06-30

  An optically active azole compound of the formula (I): wherein R¹ and R² are independently a hydrogen atom, a halogen atom, a haloalkyl group, a haloalkoxy group or an optionally substituted nitrogen-containing heterocyclic group; R³ is a hydrogen atom or an acyl group; Q is CH or N; is a nitrogen-containing aromatic five-membered heterocyclic group having at least two adjacent nitrogen atoms as the ring-constituting atoms which may be substituted, or an aromatic condensed heterocyclic group having two or more nitrogen atoms as the ring-constituting atoms which may be substituted; and (R) shows that the carbon atom marked with (R) has R-configuration; provided that either of R¹ and R² is an optionally substituted nitrogen-containing heterocyclic group when is an 1H-1,2,4-triazol-1-yl group, or a salt thereof, which is useful as an antifungal agent.

  式 (I) 的光学活性唑类化合物： 其中 R¹ 和 R² 独立地为氢原子、卤素原子、卤代烷基、卤代烷氧基或任选取代的含氮杂环基团；R³ 为氢原子或酰基；Q 为 CH 或 N； 是含氮芳香五元杂环基团，其至少有两个相邻的氮原子作为可被取代的成环原子，或者是含两个或两个以上氮原子作为可被取代的成环原子的芳香缩合杂环基团；且 (R) 表示标有 (R) 的碳原子具有 R 构型；条件是 R¹ 和 R² 中的任一基团在以下情况下是任选取代的含氮杂环基团： 1. 是 1H-1,2,4-三唑-1-基团或其盐，可用作抗真菌剂。
• US5371100A
  申请人：——

  公开号：US5371100A

  公开（公告）日：1994-12-06
• US5495024A
  申请人：——

  公开号：US5495024A

  公开（公告）日：1996-02-27