3-bromomethyl-4-(2'-bromo-2',2'-difluoroethyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3-bromomethyl-4-(2'-bromo-2',2'-difluoroethyl)tetrahydrofuran
• 英文别名: 3-(2-Bromo-2,2-difluoro-ethyl)-4-bromomethyl-tetrahydro-furan；3-(2-bromo-2,2-difluoroethyl)-4-(bromomethyl)oxolane
• 化学式: C₇H₁₀Br₂F₂O
• 分子量: 307.961
• InChiKey: XAGSWSOKNXFEJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• 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：
  3

反应信息

• 作为产物：
  描述：

  二溴二氟甲烷 、 烯丙基醚 在 sodium dithionite 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以85%的产率得到3-bromomethyl-4-(2'-bromo-2',2'-difluoroethyl)tetrahydrofuran
  参考文献：
  名称：

  磺胺脱卤试剂促进的二溴二氟甲烷加成反应

  摘要：

  描述了二氟二溴甲烷在温和条件下与亚磺酰胺脱卤化试剂，R F I /连二亚硫酸钠，Rongalite或硫脲二氧化物促进的烯烃，炔烃和环状烯醇醚的加成反应。

  DOI：

  10.1016/s0022-1139(96)03503-8

文献信息

• Addition reactions of dibromodifluoromethane promoted by sulfinatodehalogenation reagents
  作者：Fan-Hong Wu、Bing-Nan Huang、Long Lu、Wei-Yuan Huang

  DOI：10.1016/s0022-1139(96)03503-8

  日期：1996.10

  The addition reaction of difluorodibromomethane with alkenes, alkynes and cyclic enol ethers promoted by sulfinatodehalogenation reagents, RFI/sodium dithionite, Rongalite or thiourea dioxide under mild conditions are described.

  描述了二氟二溴甲烷在温和条件下与亚磺酰胺脱卤化试剂，R F I /连二亚硫酸钠，Rongalite或硫脲二氧化物促进的烯烃，炔烃和环状烯醇醚的加成反应。
• A convenient synthesis of bromodifluoromethyl-substituted alkenes
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)03051-m

  日期：1994.10

  Various functionalized bromodifluoromethyl-substituted alkenes have been prepared by addition of dibromodifluoromethane to functionalized alkenes promoted by a CrCl3/Fe bimetal redox system, followed by dehydrobromination with KF/Al2O3.
• A Straightforward Synthesis of [3.3.0]Bicyclic Compounds
  作者：I. Lachaise、K. Nohair、M. Hakiki、J. Y. Nédélec

  DOI：10.1080/00397919508015487

  日期：1995.11

  cis-3-Aza- and 3-Oxo-bicyclo[3.3.0]octane were prepared in two steps from the corresponding 1,6-dienes.
• Mechanistic Studies on Zinc-Induced Addition of CF2Br2 to Olefins. A Novel Radical Reductive Cyclopropanation on the Zinc Surface
  作者：Shi-Hui Wu、Wei-Zhong Liu、Xi-Kui Jiang

  DOI：10.1021/jo00083a030

  日期：1994.2

  The addition reaction of dibromodifluoromethane (1) to olefins induced by zinc in ethereal solvent differs surprisingly from addition reactions hitherto reported. Both cyclopropane derivatives and 1:1 addition products were obtained from this reaction. A free-radical chain addition reaction induced ; by single electron transfer (SET) is proposed. This reaction is inhibited by hydroquinone and completely quenched by p-dinitrobenzene. The nature of the 1:1 adducts formed revealed the character of a typical radical reaction. The nature of the cyclopropane derivatives formed was also much different from the usual cyclopropane adduct derived from carbene addition. When diallyl ether (15) and norbornadiene (16) were used as substrates, only rearranged 1:1 addition products could be obtained, and no cyclopropane product could be detected. The results of addition reactions with 4-octenes (27) showed also that the cyclopropanation reaction was not stereospecific. On the basis of the above-mentioned results, a novel reductive debromocyclopropanation reaction of the gamma-bromopropyl radical intermediate proceeding on the zinc metal surface is suggested.
• Oxidant-induced addition reaction of perfluoroalkyl halides to alkenes and alkynes
  作者：Xiao-Chuan Guo、Qing-Yun Chen

  DOI：10.1016/s0022-1139(97)00132-2

  日期：1998.2

  Ceric sulfate, cerium(IV) ammonium nitrate, sodium persulfate, ammonium persulfate and potassium permanganate can smoothly induce the addition reaction of perfluoroalkyl halides (1) to electron-rich olefins (2) and alkynes (4) to give monoadducts (3 or 5). The perfluoroalkyl radical generated via possible pathways from 1 is discussed. (C) 1998 Elsevier Science S.A. All rights reserved.