(2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide | 329925-77-1

• 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: (2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide
• 英文别名: (R)-N-[2-Chloro-3-fluoro-4-(ethylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide；(R)-N-(4-ethylsulphonyl-3-fluoro-2-chlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide；(2R)-N-[2-Chloro-4-(ethanesulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide；(2R)-N-(2-chloro-4-ethylsulfonyl-3-fluorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide
• CAS: 329925-77-1
• 化学式: C₁₂H₁₂ClF₄NO₄S
• 分子量: 377.744
• InChiKey: QDTNAUUGCQNAPX-LLVKDONJSA-N

物化性质

• 熔点：
  146.5-148 °C
• 沸点：
  537.0±50.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-乙酰哌嗪 、 (2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide 在 氩 、 氯化铵 、 乙醚 、 Brine 、 methanol-dichloromethane 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以to give the title compound (0.895 g) as a white foam的产率得到(R)-N-[2-Chloro-3-(4-acetylpiperazin-1-yl)-4-(ethylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide
  参考文献：
  名称：

  Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity

  摘要：

  公式(I)的化合物，其中：n为1或2；R1为氯、氟、溴、甲基或甲氧基；R2和R3如定义；R4为氢或氟；或其药学上可接受的盐或体内可水解的酯。还描述了在温血动物（如人类）中使用公式(I)的化合物来提高PDH活性。详细描述了制备公式(I)化合物的制药组合物、方法和过程。

  公开号：

  US06689909B1
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯酚 在 氯化亚砜 、 sodium dithionite 、 双氧水 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 66.5h， 生成 (2R)-N-[2-chloro-4-(ethylsulfonyl)-3-fluorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide
  参考文献：
  名称：

  Kepner-Tregoe Decision Analysis as a Tool To Aid Route Selection. Part 3. Application to a Back-Up Series of Compounds in the PDK Project

  摘要：

  Kepner-Tregoe Decision Analysis was used to rank 22 potential routes to a back-up series of compounds in the PDK project. The ten highest scoring routes were evaluated practically, affording four new synthetic sequences for preparing the target compounds.

  DOI：

  10.1021/op8000355

文献信息

• Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3-trifluropropanamide derivatives which elevate pyruvate dehydrogenase activity
  申请人：Butlin John Roger

  公开号：US20050026931A1

  公开（公告）日：2005-02-03

  Compounds of formula (I) wherein R is methyl or mesyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters thereof are described. Also described are processes for their preparation, pharmaceutical compositions containing it and their use in producing an elevation of PDH activity in a warm-blooded animal.

  本文描述了化学式（I）的化合物，其中R为甲基或甲磺基；以及其药学上可接受的盐和体内可水解的酯。还描述了它们的制备过程，包括含有它们的制药组合物以及它们在产生温血动物中PDH活性升高方面的用途。
• Chemical compounds
  申请人：Butlin John Roger

  公开号：US20070208032A1

  公开（公告）日：2007-09-06

  Compounds of formula (I) wherein R is methyl or mesyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters thereof are described. Also described are processes for their preparation, pharmaceutical compositions containing it and their use in producing an elevation of PDH activity in a warm-blooded animal.

  描述了化学式（I）的化合物，其中R是甲基或甲磺酰基；以及其药学上可接受的盐和体内可水解的酯。还描述了制备它们的过程，含有它们的制药组合物以及它们在产生温血动物的PDH活性升高方面的用途。
• SUBSTITUTED N-PHENYL 2-HYDROXY-2-METHYL-3,3,3-TRIFLUOROPROPANAMIDE DERIVATIVES WHICH ELEVATE PYRUVATE DEHYDROGENASE ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1214296B1

  公开（公告）日：2004-03-24
• US6689909B1
  申请人：——

  公开号：US6689909B1

  公开（公告）日：2004-02-10
• [EN] SUBSTITUTED N-PHENYL 2-HYDROXY-2-METHYL-3,3,3-TRIFLUOROPROPANAMIDE DERIVATIVES WHICH ELEVATE PYRUVATE DEHYDROGENASE ACTIVITY<br/>[FR] DERIVES DE N-PHENYL 2-HYDROXY-2-METHYL-3,3,3-TRIFLUOROPROPANAMIDE SUBSTITUES DESTINES A AUGMENTER L'ACTIVITE DE PYRUVATE DESHYDROGENASE
  申请人：ASTRAZENECA AB

  公开号：WO2001017956A1

  公开（公告）日：2001-03-15

  A compound of formula (I) wherein: n is 1 or 2; R1 is chloro, fluoro, bromo, methyl or methoxy; R2 is as defined within; R3 is as defined within; and R4 is hydrogen or fluoro; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed.