罗氟烷 | 679-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 罗氟烷
• 英文名称: Roflurane
• 英文别名: bromo-2-trifluoro-1,1,2-ethyl-methyl ether；1,1,2-trifluoro-2-bromoethyl ether；Methyl-<1,1,2-trifluor-2-brom-aethyl>-aether；1,1,2-Trifluor-2-bromethylmethylether；2-bromo-1,1,2-trifluoro-1-methoxyethane
• CAS: 679-90-3
• 化学式: C₃H₄BrF₃O
• 分子量: 192.963
• InChiKey: YOQYDUAUSFAUER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 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：
  4

反应信息

• 作为反应物：
  描述：

  罗氟烷 在 三乙基硅烷 、 palladium dichloride 作用下， 反应 3.5h， 以77.8%的产率得到1,1,2-三氟-1-甲氧基乙烷
  参考文献：
  名称：

  通过三氟化溴和其他方法实际制备潜在麻醉的氟化乙基甲基醚

  摘要：

  描述了合成方法，特别是使用三氟化溴作为氟化剂的合成方法，以高收率和高纯度制备许多氟化乙基甲基醚。在所有情况下，已经完成了中等规模的合成（8–22 g）潜在的麻醉剂。这些化合物具有足够的纯度（> 99％）用于生物学评估。

  DOI：

  10.1016/s0022-1139(99)00302-4
• 作为产物：
  描述：

  甲醇 、 溴代三氟代乙烯 在 sodium 作用下， 生成 罗氟烷
  参考文献：
  名称：

  Addition of Alcohols to Fluorinated Ethylenes

  摘要：

  DOI：

  10.1021/jo01076a033

文献信息

• Observation of a competitive path in the nucleophilic addition of fluoroolefins: The bromophilic reaction of the adduct carbanion intermediate
  作者：Xi-Kui Jiang、Guo-Zhen Ji、Yi-Qun Shi

  DOI：10.1016/s0022-1139(00)81976-4

  日期：1987.12

  products ROCF2CFBr2 (6) have been obtained in the reactions of bromotrifluoroethene(3) with different alkoxides (RO- = t-BuO-, i-PrO-, EtO- and MeO-). These products(6) are formed from a competitive path involving bromophilic reactions of the intermediate adduct carbanions(8). Radicals have been shown to be unlikely intermediates of this competitive reaction path.

  除了氢烷氧基加成产物ROCF 2 CFBrH（4）和烯烃产物ROCFCFBr（5）以外，一种新型产品，即烷氧基-溴加成产物ROCF 2 CFBr 2（6）还具有在bromotrifluoroethene（3）具有不同醇盐的反应获得（RO - =叔迪布奥- ，我-PRO - ，环氧乙烷-和的MeO - ）。这些产品（6）是通过竞争途径形成的，该竞争途径涉及中间加合物碳负离子（8）的亲核反应。自由基已被证明是这种竞争性反应途径的中间产物。
• General anesthetics. 1. Halogenated methyl ethyl ethers as anesthetic agents
  作者：Ross C. Terrell、Louise Speers、Alex J. Szur、John Treadwell、Thomas R. Ucciardi

  DOI：10.1021/jm00288a014

  日期：1971.6
• Nucleophilic reactions at vinylic center. 27. Vinylic substitution of 1,2-dibromo-1,2-difluoroethylene and tribromofluoroethylene. An intramolecular kBr/kF element effect and apparent inversion of configuration in SNV reactions
  作者：Bagrat A. Shainyan、Zvi Rappoport

  DOI：10.1021/jo00064a036

  日期：1993.6

  The reactions of (E/Z)-1,2-dibromo-1,2-difluoroethylene (1) and of tribromofluoroethylene (2) with alkoxide ions and of 1 with p-toluenethiolate ion give multiplicity of products. The reaction of 1 with 1 equiv of NaOMe gives mainly a 2:1 mixture of the product of one bromine displacement, together with methyl dimethoxyacetate (3), methyl bromofluoroacetate (4), 1,1,2-trifluoro-2-bromoethyl ether (7), and 1,1-difluoro-1,2,2-trimethoxyethane (8). With 2 equiv of MeO- 3 and 4 are the main products, and at 130-degrees-C, dimethyl ether 5 is also formed. With EtOCH2CH2O- 1 gave 2-ethoxyethyl bromofluoroacetate (9), bis(2-ethoxyethyl) ether (10), and E/Z mixtures of the substitution products EtOCH2CH2OC(F)=C(F)Br (12) and EtOCH2CH2OC(Br)=C(F)Br (13). Reaction of 2 with excess RO- (R=Me, Et) gives alkyl dibromoacetates, while with 1 equiv of RO- only a bromine from the =C(F)Br carbon is displaced. Reaction of l with p-TolSNa in MeOH gives the reduction-substitution product p-TolSC(F)=CHF(18), together with (p-TolS)2(16) and p-TolSMe (17). The same reaction in DMSO gives E/Z mixtures of the product of displacement of one bromine (19) or two bromines (20). Formation of the products is rationalized by an initial nucleophilic attack on the vinylic carbon followed by leaving group expulsion, giving, e.g., 12, 13, 19, or 20. Hydrolysis of the intermediate or addition of HF to the initial substitution product gives saturated products, e.g., 3,4,7, or 8, while S(N)2 reactions on the ether oxygen give ethers 5 and 10. A bromophilic reaction gives the reduction-substitution product 18, while hydrolysis-decarboxylation leads to 17. The regiospecificity of the nucleophilic addition is due to polar and hyperconjugative effects. An intramolecular element effect k(Br)/k(F) Of >10 is reported for the first time in the reaction of 1 with EtOCH2CH2O-. This value and the absence of such effects in other reactions are consistent with a much higher nucleofugality from a -CC(F)Br system of Br- compared with F-. The E/Z compositions of 18-20 indicates an apparent inversion in their formation, but it is not known whether these compositions are thermodynamically or kinetically controlled.
• Hydrolysis of Fluorinated Ethers
  作者：Eric R. Larsen

  DOI：10.1021/jo01039a506

  日期：1963.4
• Shainyan Bagrat A., Rappoport Zvi, J. Org. Chem., 58 (1993) N 12, S 3421-3428
  作者：Shainyan Bagrat A., Rappoport Zvi

  DOI：——

  日期：——