1-溴-2-(溴二氟甲基)环己烷 | 14737-09-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 中文名称: 1-溴-2-(溴二氟甲基)环己烷
• 英文名称: cis/trans-1-bromodifluoromethyl-2-bromocyclohexane
• 英文别名: 2-bromo-1-bromodifluoromethylcyclohexane；1-Bromo-2-(bromodifluoromethyl)cyclohexane；1-bromo-2-[bromo(difluoro)methyl]cyclohexane
• CAS: 14737-09-8
• 化学式: C₇H₁₀Br₂F₂
• 分子量: 291.961
• InChiKey: MWCUYVZBWZWWKO-UHFFFAOYSA-N

物化性质

• 沸点：
  108 °C
• 密度：
  1.806±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2903890090
• 安全说明：
  S26,S36

反应信息

• 作为反应物：
  描述：

  1-溴-2-(溴二氟甲基)环己烷 在 锌 作用下， 以 乙醚 为溶剂， 以19%的产率得到7,7-difluoronorcarane
  参考文献：
  名称：

  Mechanistic Studies on Zinc-Induced Addition of CF2Br2 to Olefins. A Novel Radical Reductive Cyclopropanation on the Zinc Surface

  摘要：

  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.

  DOI：

  10.1021/jo00083a030
• 作为产物：
  描述：

  二溴二氟甲烷 、 环己烯 在 chromium chloride 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 1-溴-2-(溴二氟甲基)环己烷
  参考文献：
  名称：

  Synthesis of bromodifluoromethyl-substituted alkenes. Potassium fluoride supported on alumina as a dehydrobrominating agent

  摘要：

  Potassium fluoride supported on alumina is an efficient dehydrobrominating agent. 1,3-Dibromo-1,1-difluoroalkanes - adducts of dibromodifluoromethane and alkenes - give bromodifluoromethyl-substituted alkenes 2 on dehydrobromination with this agent in good to excellent yields. Alkenes 2 were a mixture of Z- and E-isomers, with the former predominating. Functional groups such as ester, carbonyl, ethylenic and chloromethyl are not affected under such reaction conditions.

  DOI：

  10.1016/0022-1139(93)02954-d

文献信息

• 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.
• Difluoromethylation of alkenes via borohydride reduction of 1,3-dibromo-1,1-difluoroalkanes
  作者：Javier Gonzalez、Christopher J. Foti、Seth Elsheimer

  DOI：10.1021/jo00013a051

  日期：1991.6
• Unexpected products from the reactions of 1-(bromodifluoromethyl)-2-bromocyclohexanes with potassium hydroxide
  作者：Seth Elsheimer、Mariana Michael、Antonio Landavazo、Darlene K. Slattery、Jennifer Weeks

  DOI：10.1021/jo00261a041

  日期：1988.12
• GONZALEZ, JAVIER;FOTI, CHRISTOPHER J.;ELSHEIMER, SETH, J. ORG. CHEM., 56,(1991) N3, C. 4322-4325
  作者：GONZALEZ, JAVIER、FOTI, CHRISTOPHER J.、ELSHEIMER, SETH

  DOI：——

  日期：——
• Synthesis of bromodifluoromethyl-substituted alkenes. Potassium fluoride supported on alumina as a dehydrobrominating agent
  作者：Chang-Ming Hu、Jian Chen

  DOI：10.1016/0022-1139(93)02954-d

  日期：1994.1

  Potassium fluoride supported on alumina is an efficient dehydrobrominating agent. 1,3-Dibromo-1,1-difluoroalkanes - adducts of dibromodifluoromethane and alkenes - give bromodifluoromethyl-substituted alkenes 2 on dehydrobromination with this agent in good to excellent yields. Alkenes 2 were a mixture of Z- and E-isomers, with the former predominating. Functional groups such as ester, carbonyl, ethylenic and chloromethyl are not affected under such reaction conditions.