<(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethyl> benzoate | 150802-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethyl> benzoate
• 英文别名: [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate；[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate；[(1S)-1-[(2R)-2-(2,4-difluorophenyl)oxiran-2-yl]ethyl] benzoate
• CAS: 150802-85-0
• 化学式: C₁₇H₁₄F₂O₃
• 分子量: 304.293
• InChiKey: AYMWCFJKFUJQSB-APPDUMDISA-N

物化性质

• 沸点：
  382.2±42.0 °C(predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethyl> benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以93%的产率得到(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol
  参考文献：
  名称：

  Optically Active Antifungal Azoles. VI. Synthesis and Antifungal Activity of N-((1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl)-N'-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones.

  摘要：

  通过(1S)-1-[(2R)-2-(2,4-二氟苯基)-2-环氧乙烷基]乙醇的三氟甲磺酸酯衍生物与一种吖唑酮阴离子经SN2取代反应及随后与1H-1,2,4-三氮唑的开环反应制备了一系列具有光学活性的新型抗真菌唑类化合物，N-[(1R,2R)-2-(2,4-二氟苯基)-2-羟基-1-甲基-3-(1H-1,2,4-三唑-1-基)丙基]-N'-(4-取代苯基)-3(2H,4H)-1,2,4-三唑酮(1,2)和5(1H,4H)-四唑酮(3)。手性环氧乙烷乙醇13是以立体控制方式由甲基(R)-乳酸制得。所制得的吖唑酮1-3在体外及体内均展现出强大的抗真菌活性。

  DOI：

  10.1248/cpb.44.314
• 作为产物：
  描述：

  2-((1R)-1-(2-(2,4-二氟苯基)氧基-2-基)乙氧基)四氢-2H-吡喃 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 <(1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethyl> benzoate
  参考文献：
  名称：

  Optically Active Antifungal Azoles. VI. Synthesis and Antifungal Activity of N-((1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl)-N'-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones.

  摘要：

  通过(1S)-1-[(2R)-2-(2,4-二氟苯基)-2-环氧乙烷基]乙醇的三氟甲磺酸酯衍生物与一种吖唑酮阴离子经SN2取代反应及随后与1H-1,2,4-三氮唑的开环反应制备了一系列具有光学活性的新型抗真菌唑类化合物，N-[(1R,2R)-2-(2,4-二氟苯基)-2-羟基-1-甲基-3-(1H-1,2,4-三唑-1-基)丙基]-N'-(4-取代苯基)-3(2H,4H)-1,2,4-三唑酮(1,2)和5(1H,4H)-四唑酮(3)。手性环氧乙烷乙醇13是以立体控制方式由甲基(R)-乳酸制得。所制得的吖唑酮1-3在体外及体内均展现出强大的抗真菌活性。

  DOI：

  10.1248/cpb.44.314

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。
• Production of Di or tri-azolyl substituted 5-keto azole compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05466820A1

  公开（公告）日：1995-11-14

  An azole compound represented by the formula (I): ##STR1## wherein Ar is a substituted phenyl group; R.sup.1 and R.sup.2 independently are a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may combine together to form a lower alkylene group; R.sup.3 is a group bonded through a carbon atom; R.sup.4 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; and Y and Z independently are a nitrogen atom or a methine group which may optionally be substituted with a lower alkyl group, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.

  一种以式子（I）表示的唑类化合物：##STR1## 其中Ar是一个取代的苯基；R.sup.1和R.sup.2分别是氢原子或较低的烷基基团，或R.sup.1和R.sup.2可以结合形成较低的烷基烷基基团；R.sup.3是通过碳原子连接的基团；R.sup.4是氢原子或酰基基团；X是氮原子或甲基基团；Y和Z分别是氮原子或甲基基团，可以选择性地用较低的烷基基团取代，或其盐，用作哺乳动物真菌感染的预防和治疗的抗真菌剂。
• 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。
• Triazole and imidazole compounds and their use as antifungal therapeutic
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05545652A1

  公开（公告）日：1996-08-13

  The present invention provides an azole compound represented by the formula (I): ##STR1## wherein Ar is an optionally-substituted phenyl group; R.sup.1 and R.sup.2 are, the same or different, a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may combine together to form a lower alkylene group; R.sup.3 is a hydrogen atom or an acyl group; Y is a nitrogen atom or a methine group; and A is an optionally-substituted saturated cyclic amide group bonded through a first nitrogen atom, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.

  本发明提供一种由公式(I)表示的唑类化合物：##STR1## 其中Ar是可选取代的苯基；R1和R2是相同或不同的氢原子或低烷基，或者R1和R2可以结合形成低烷基烷基；R3是氢原子或酰基基团；Y是氮原子或甲基基团；A是可选取代的饱和环酰胺基团，通过第一氮原子结合，或其盐，用作哺乳动物真菌感染的预防和治疗的抗真菌剂。
• Injectable composition and a method of producing the same
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05814324A1

  公开（公告）日：1998-09-29

  An injectable oil-in-water emulsion composition comprises an antifungal triazole compound of the following formula (I) ##STR1## wherein Ar represents a substituted phenyl group; R.sup.1 and R.sup.2 represent, independently, a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 may together form a lower alkylene group; R.sup.4 represents a hydrogen atom or an acyl group; and A represents an optionally substituted cyclic amide group bonded through a nitrogen atom, or a salt thereof. The solubility of the triazole compound having poor water-solubility and fat-solubility can remarkably be increased by dispersing in water with use of an oil component (e.g. a triglyceride of fatty acids) and an emulsifier (e.g. a phospholipid).

  一种可注射的油水乳液组成物包括以下式(I)的抗真菌三唑类化合物：##STR1## 其中Ar代表取代的苯基；R1和R2分别代表氢原子或较低的烷基，或R1和R2可以共同形成较低的烷基；R4代表氢原子或酰基；A代表通过氮原子结合的可选取代的环状酰胺基团，或其盐。通过使用油组分（例如脂肪酸甘油三酯）和乳化剂（例如磷脂）在水中分散，可以显著提高水溶性和脂溶性较差的三唑类化合物的溶解度。