2-[氯(氟)甲氧基]-1,1,1,2-四氟乙烷 | 56885-28-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 中文名称: 2-[氯(氟)甲氧基]-1,1,1,2-四氟乙烷
• 英文名称: rac-1,2,2,2-Tetrafluoroethyl chlorofluoromethyl ether
• 英文别名: 1,2,2,2-tetrafluoroethyl fluorochloromethyl ether；2-[Chloro(fluoro)methoxy]-1,1,1,2-tetrafluoroethane
• CAS: 56885-28-0
• 化学式: C₃H₂ClF₅O
• 分子量: 184.493
• InChiKey: GGEBMRHBGQLKGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R,S)-1,2,2,2-Tetrafluoroethyl dichlorofluoromethyl ether 在 异丙醇 作用下， 反应 6.0h， 以49%的产率得到2-[氯(氟)甲氧基]-1,1,1,2-四氟乙烷
  参考文献：
  名称：

  Asymmetric Synthesis of the Volatile Anesthetic 1,2,2,2-Tetrafluoroethyl Chlorofluoromethyl Ether Using a Stereospecific Decarboxylation of Unusual Stereochemical Outcome

  摘要：

  Acid 1 is optically resolved by diastereomeric amide formation/chromatography/hydrolysis. Decarboxylation of the enantiomers of acid 1 gives the enantiomers of ether 2 with a very high degree of stereospecificity. The absolute configurations of both the starting acid and the ether product are determined to be (R)-(+) and(S)-(-). The data indicate that decarboxylation occurs with clean inversion of configuration. A mechanism is proposed to rationalize this. unusual result. The enantiomers of ether 2 are converted to diastereomers of the volatile anesthetic 3 by a route consisting of trichlorination of the methyl group to give 9, monofluorination to yield 10, and monoreduction to afford the target anesthetic.

  DOI：

  10.1021/jo00110a041

文献信息

• Production Method for 1,2,2,2-Tetrafluoroethyl Difluoromethyl Ether (Desflurane)
  申请人：Central Glass Company, Limited

  公开号：US20190345086A1

  公开（公告）日：2019-11-14

  Fluoral is obtained by gas-phase fluorination of chloral in the presence of a catalyst and then reacted with trimethyl orthoformate, thereby readily forming 1,2,2,2-tetrafluoroethyl methyl ether as an intermediate for production of desflurane. 1,2,2,2-Tetrafluoroethyl difluoromethyl ether (desflurane) is produced with high yield from the thus-formed 1,2,2,2-tetrafluoroethyl methyl ether by chlorination and fluorination. This method enables efficient industrial-scale production of desflurane useful as an inhalation anesthetic

  Fluoral是在催化剂存在下通过气相氟化氯醛获得，然后与三甲基正甲酸酯反应，从而轻松形成1,2,2,2-四氟乙基甲醚作为生产地氟醚的中间体。通过氯化和氟化反应，可以高产率地从形成的1,2,2,2-四氟乙基甲醚中生产1,2,2,2-四氟乙基二氟甲基醚（地氟醚）。该方法能够有效地工业规模生产地氟醚，作为吸入麻醉剂使用。
• Asymmetric Synthesis of the Volatile Anesthetic 1,2,2,2-Tetrafluoroethyl Chlorofluoromethyl Ether Using a Stereospecific Decarboxylation of Unusual Stereochemical Outcome
  作者：Leonid A. Rozov、Patrice W. Rafalko、Suzanne M. Evans、Linda Brockunier、Keith Ramig

  DOI：10.1021/jo00110a041

  日期：1995.3

  Acid 1 is optically resolved by diastereomeric amide formation/chromatography/hydrolysis. Decarboxylation of the enantiomers of acid 1 gives the enantiomers of ether 2 with a very high degree of stereospecificity. The absolute configurations of both the starting acid and the ether product are determined to be (R)-(+) and(S)-(-). The data indicate that decarboxylation occurs with clean inversion of configuration. A mechanism is proposed to rationalize this. unusual result. The enantiomers of ether 2 are converted to diastereomers of the volatile anesthetic 3 by a route consisting of trichlorination of the methyl group to give 9, monofluorination to yield 10, and monoreduction to afford the target anesthetic.