(alphaR,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁酰胺 | 219872-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (alphaR,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁酰胺
• 中文别名: 伊沙唑唑杂质H
• 英文名称: (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide
• 英文别名: (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-ylbutyramide；(Alphar,betar)-beta-(2,4-difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanamide；(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanamide
• CAS: 219872-85-2
• 化学式: C₁₃H₁₄F₂N₄O₂
• 分子量: 296.277
• InChiKey: OYZNOUGSYGBXCY-ISVAXAHUSA-N

物化性质

• 熔点：
  160-162°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (alphaR,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁酰胺 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85 g的产率得到(alphaS,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁腈
  参考文献：
  名称：

  [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES
  [FR] PROCÉDÉ AMÉLIORÉ POUR LA PRÉPARATION DE DÉRIVÉS DE TRIAZOLE

  摘要：

  本发明涉及一种改进的工艺，用于制备三唑衍生物，如拉伏康唑和伊沙伏康唑。

  公开号：

  WO2021245590A1
• 作为产物：
  描述：

  (alphaS,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁腈 在 双氧水 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 以82%的产率得到(alphaR,betaR)-beta-(2,4-二氟苯基)-beta-羟基-alpha-甲基-1H-1,2,4-三唑-1-丁酰胺
  参考文献：
  名称：

  Carbon analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities

  摘要：

  A new series of triazole compounds possessing a carbon atom in place of a sulfur atom were efficiently synthesized and their in vitro antifungal activities were investigated. The carbon analogs showed excellent in vitro activity against Candida, Cryptococcus, and Aspergillus species. The MICs of compound 1c against C. albicans ATCC24433, C. neoformans TIMM1855, and A. fumigatus ATCC26430 were 0.016, 0.016, and 0.125 mu g/mL, respectively (MICs of fluconazole: 0.5, >4, and >4 mu g/mL; MICs of itraconazole: 0.125, 0.25, and 0.25 mu g/mL). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.055

文献信息

• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES<br/>[FR] PROCÉDÉ AMÉLIORÉ POUR LA PRÉPARATION DE DÉRIVÉS DE TRIAZOLE
  申请人：METROCHEM API PRIVATE LTD

  公开号：WO2021245590A1

  公开（公告）日：2021-12-09

  The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

  本发明涉及一种改进的工艺，用于制备三唑衍生物，如拉伏康唑和伊沙伏康唑。
• Carbon analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities
  作者：Takuya Uchida、Atsushi Somada、Yoshiko Kagoshima、Toshiyuki Konosu、Sadao Oida

  DOI：10.1016/j.bmcl.2008.10.055

  日期：2008.12

  A new series of triazole compounds possessing a carbon atom in place of a sulfur atom were efficiently synthesized and their in vitro antifungal activities were investigated. The carbon analogs showed excellent in vitro activity against Candida, Cryptococcus, and Aspergillus species. The MICs of compound 1c against C. albicans ATCC24433, C. neoformans TIMM1855, and A. fumigatus ATCC26430 were 0.016, 0.016, and 0.125 mu g/mL, respectively (MICs of fluconazole: 0.5, >4, and >4 mu g/mL; MICs of itraconazole: 0.125, 0.25, and 0.25 mu g/mL). (C) 2008 Elsevier Ltd. All rights reserved.
• Improved Chiral Synthesis of Ravuconazole
  作者：Lin Xu、Marc R. Muller、Xiong Yu、Bao-Quan Zhu

  DOI：10.1080/00397910802563420

  日期：2009.4.7

  A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate.