1,1,3,3,3-五氟-2-(氟甲氧基)-1-丙烯 | 58109-34-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1,1,3,3,3-五氟-2-(氟甲氧基)-1-丙烯
• 中文别名: 氟甲基全氟异丙烯基醚；氟甲基1,1,3,3,3-五氟-2-丙烯基醚；七氟烷相关物质A
• 英文名称: fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether
• 英文别名: fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether；1,1,3,3,3-pentafluoro-2-(fluoromethoxy)prop-1-ene；2-(fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene；Compound A
• CAS: 58109-34-5
• 化学式: C₄H₂F₆O
• 分子量: 180.05
• InChiKey: VMCHRPIQINOPJR-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1,1,3,3,3-五氟-2-(氟甲氧基)-1-丙烯 在 四氯化碳 、 氯化锑(V) 作用下， 反应 1.0h， 以57%的产率得到1-Propene, 2-(chloromethoxy)-1,1,3,3,3-pentafluoro-
  参考文献：
  名称：

  The fluoromethyl ether sevoflurane as a fluoride source in halogen-exchange reactions

  摘要：

  Fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether (sevoflurane), fluoromethyl 1,1,2,3,3,3-hexafluoropropyl ether, and fluoromethyl 1,2,2,2-tetrafluoroethyl ether are found to be selective fluoride donors in some halogen-exchange reactions. For example, treatment of a mixture of a polychlorinated substrate and one equivalent of sevoflurane with a catalytic amount of antimony pentachloride gives a monofluorinated product and one equivalent of chloromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether as by-product. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(97)00135-8
• 作为产物：
  描述：

  七氟烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 1,1,3,3,3-五氟-2-(氟甲氧基)-1-丙烯
  参考文献：
  名称：

  详细研究氟甲基1,1,1,3,3,3-六氟-2-丙基醚（七氟醚）及其降解产物。第一部分：氟化苏打石灰诱导的降解产物的合成

  摘要：

  七氟醚（I），氟甲基1,1,3,3,3,5-五氟-2-丙烯醚（II），氟甲基1-甲氧基-1,1,3,3,3-五氟-分别独立合成了2-丙基醚（III）和氟甲基1-甲氧基-1,3,3,3-四氟-2-丙烯基醚（IV）。在（II）的合成中，分离了副产物氟甲基1-氰基-2,2,2-三氟乙基醚（V）。

  DOI：

  10.1016/s0022-1139(00)84149-4

文献信息

• METHODS FOR PREPARING FLUORINATED VINYL ETHERS
  申请人：Huang Chialang Grand

  公开号：US20100267995A1

  公开（公告）日：2010-10-21

  A method for preparing a fluorinated vinyl ether compound comprising reacting a fluorinated ether substrate having (i) a hydrogen atom on a carbon atom that is alpha to an etheric oxygen and (ii) a fluorine atom on a carbon atom that is beta to the etheric oxygen, with an organolithium base to provide a reaction product comprising a fluorinated vinyl ether compound.

  一种制备氟化乙烯醚化合物的方法，包括将一种氟化醚底物与有机锂碱反应，所述氟化醚底物具有(i) 一个氢原子位于与乙醚氧原子相邻的碳原子的α位上，以及(ii) 一个氟原子位于与乙醚氧原子相邻的碳原子的β位上，以提供包含氟化乙烯醚化合物的反应产物。
• Methods for preparing fluorinated vinyl ethers
  申请人：Huang Chialang Grand

  公开号：US09353038B2

  公开（公告）日：2016-05-31

  A method for preparing a fluorinated vinyl ether compound comprising reacting a fluorinated ether substrate having (i) a hydrogen atom on a carbon atom that is alpha to an etheric oxygen and (ii) a fluorine atom on a carbon atom that is beta to the etheric oxygen, with an organolithium base to provide a reaction product comprising a fluorinated vinyl ether compound.

  一种制备含氟乙烯醚化合物的方法，包括将具有以下特征的含氟醚底物与有机锂碱反应：(i)在乙醚氧原子的α-碳上具有氢原子；(ii)在乙醚氧原子的β-碳上具有氟原子，从而得到反应产物，其中包括含氟乙烯醚化合物。
• Iyer, Ramaswamy A.; Baggs, Raymond B.; Anders, Journal of Pharmacology and Experimental Therapeutics, 1997, vol. 283, # 3, p. 1544 - 1551
  作者：Iyer, Ramaswamy A.、Baggs, Raymond B.、Anders

  DOI：——

  日期：——
• Identification in Rat Bile of Glutathione Conjugates of Fluoromethyl 2,2-Difluoro-1-(trifluoromethyl)vinyl Ether, a Nephrotoxic Degradate of the Anesthetic Agent Sevoflurane
  作者：Lixia Jin、Margaret R. Davis、Evan D. Kharasch、George A. Doss、Thomas A. Baillie

  DOI：10.1021/tx950162m

  日期：1996.1.1

  Recent studies have indicated that the nephrotoxicity of fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether (''Compound A''), a breakdown product of the inhaled anesthetic sevoflurane, may be mediated by a reactive intermediate(s) generated via the cysteine conjugate beta-lyase pathway. In order to gain a better understanding of glutathione (GSH)-dependent metabolism of Compound A, the present study was carried out with the primary goal of detecting and characterizing Compound A-GSH conjugates. By means of ionspray LC-MSI MS and NMR spectroscopy, a total of four GSH conjugates (''A1-A4'') were identified from the bile of rats dosed intraperitoneally with Compound A. A1 and A2 were identified as two diastereomers of S-[1,1-difluoro-2-(fluoromethoxy)-2-(trifluoromethyl)ethyl]glutathione, while A3 and A4 were identified as (E)- and (Z)S-[1-fluoro-2-(fluoromethoxy)-2-(trifluoromethyl)-vinyl]glutathione, respectively. Quantitative analyses indicated that approximately 29% of the administered dose of Compound A was excreted into the bile in the form of the above GSH conjugates over a period of 6 h. Studies conducted in vitro demonstrated that the reaction of Compound A with GSH was catalyzed by both rat liver cytosolic and microsomal glutathione S-transferases (GST), with the two enzyme systems exhibiting different product selectivities. Formation of these GSH conjugates also occurred nonenzymatically at an appreciable rate. These results indicate that spontaneous and enzyme-mediated conjugation with GSH represents a major pathway of metabolism of Compound A in rats. Conjugation of Compound A with GSH in, vivo appeared to be catalyzed preferentially by microsomal rather than cytosolic GST, based on comparison of biliary, microsomal, and cytosolic metabolic profiles. By analogy with other haloalkenes, further metabolism of the corresponding cysteine conjugates of Compound A by renal cysteine conjugate beta-lyase may lead to the formation of reactive acylating agents, which would be expected to bind covalently to cellular macromolecules and cause organ-selective nephrotoxicity.
• Evidence for Metabolism of Fluoromethyl 2,2-Difluoro-1-(trifluoromethyl)vinyl Ether (Compound A), a Sevoflurane Degradation Product, by Cysteine Conjugate β-Lyase
  作者：Douglas K. Spracklin、Evan D. Kharasch

  DOI：10.1021/tx9502103

  日期：1996.1.1

  The volatile anesthetic sevoflurane is degraded to fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether (FDVE), a potent rat nephrotoxin. In rats in vivo, FDVE undergoes glutathione conjugation and metabolism to cysteine conjugates, whose bioactivation by renal cysteine conjugate beta-lyase has been implicated by the protective effects of (aminooxy)acetic acid, an inhibitor of cysteine conjugate beta-lyase. We specifically tested the hypothesis that FDVE is metabolized via the beta-lyase pathway to yield 3,3,3-trifluoro-2-(fluoromethoxy)propanoic acid. Urine of rats administered FDVE (0.3 mmol/kg) was extracted and derivatized with diazomethane. Headspace GC/MS analysis demonstrated a peak whose retention time and mass spectrum were identical to those of synthetic methyl 3,3,3-trifluoro-2-(fluoromethoxy)propanoate. Pretreatment of rats with (aminooxy)acetic acid significantly decreased the amount of 3,3,3-trifluoro-2-(fluoromethoxy)propanoic acid detected in the urine of FDVE-treated animals. The F-19 NMR spectrum of urine from rats administered FDVE was consistent with the formation of 3,3,3-trifluoro-2-(fluoromethoxy)propanoic acid, but could not be differentiated from that of FDVE mercapturates, which are also excreted in urine. These results suggest that FDVE undergoes biotransformation via the beta-lyase pathway and beta-lyase-catalyzed metabolism may mediate the nephrotoxicity of this compound.