2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷 | 68224-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷
• 英文名称: 2-[(2-Bromo-4-methylphenoxy)methyl]oxirane
• CAS: 68224-00-0
• 化学式: C₁₀H₁₁BrO₂
• mdl: MFCD11156076
• 分子量: 243.1
• InChiKey: DAQKAYNUNRPQFT-UHFFFAOYSA-N

物化性质

• 沸点：
  310.1±22.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷 在 高氯酸四乙基铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 以80%的产率得到对叔丁基苯基1-(2,3-环氧)丙基醚
  参考文献：
  名称：

  Selective Reduction of the CarbonBromine Bond in Bromo Epoxides

  摘要：

  The controlled-potential electrolysis of various substituted bromo epoxides in acetonitrile at a mercury pool electrode led to selective reduction of the carbon-bromine bond affording the respective epoxide products in 80-90% yield.

  DOI：

  10.1016/s0040-4039(00)91658-7
• 作为产物：
  描述：

  2-溴-4-甲基苯酚 、 环氧氯丙烷 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 2-[(2-溴-4-甲基苯氧基)甲基]环氧乙烷
  参考文献：
  名称：

  Selective Reduction of the CarbonBromine Bond in Bromo Epoxides

  摘要：

  The controlled-potential electrolysis of various substituted bromo epoxides in acetonitrile at a mercury pool electrode led to selective reduction of the carbon-bromine bond affording the respective epoxide products in 80-90% yield.

  DOI：

  10.1016/s0040-4039(00)91658-7

文献信息

• Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes
  作者：Reuben D. Rieke、Douglas E. Stack、Bryan T. Dawson、Tse Chong Wu

  DOI：10.1021/jo00061a023

  日期：1993.4

  The preparation of highly reactive copper by the reduction of CuI.PBu3, CuI.PPh3, and CuCN-nLiX copper(I) complexes with the preformed lithium naphthalenide is described. It was found, for all three Cu(I) complexes, that the reduction temperature proved crucial to reactivity of the zerovalent copper species as measured by the ability of the active copper to undergo oxidative addition to carbon-halogen bonds. The lower the reduction temperature the more reactive the zerovalent copper species becomes. The low-temperature reduction allows for the formation of highly reactive copper from CuCN.nLiX complexes. This active copper species undergoes oxidative addition to alkyl and aryl bromides in high yield to form the corresponding organocopper reagent directly without the need for other organometallic precursors. Moreover, the alkyl and aryl bromides can contain a wide range of functional groups as they are not affected in the oxidative addition step. The functionalized organocopper reagents derived from CuCN-nLiX based active copper are the reagent of choice in the cross-coupling of acid chlorides to produce ketones as well as the 1,4-addition reaction with enones. The lack of phosphines associated with organocopper reagents stemming from CuCN-based active copper makes product isolation more facile. While the functionalized organocopper reagents derived from CuCN.nLiX complexes provide higher isolated yields in the formentioned reactions, they are not nucleophilic enough to undergo inter- or intramolecular epoxide openings. The use of both CuI.PBu3 and CuI.PPh3 Cu(I) complexes in the intramolecular epoxide openings of aryl bromoepoxides is presented. The regiochemistry, endo vs. exo, was shown to be affected by the Cu(I) complex used to generate the active copper species, the solvent, and the pattern of substitution around the epoxide moiety. The active copper species as well as the the resulting organocopper reagents derived from both CuI.PBu3 and CuCN-nLiX were investigated using both P-31 and C-13 NMR. The data from P-31 NMR investigation held some evidence for a highly reduced copper(0)-phosphine complex while the C-13 studies of the CuCN-nLiX complexes indicated that these species have limited solubility in THF.
• BRADSHER C. K.; REAMES D. C., J. ORG. CHEM., 1978, 43, NO 19, 3800-3802
  作者：BRADSHER C. K.、 REAMES D. C.

  DOI：——

  日期：——
• Selective Reduction of the CarbonBromine Bond in Bromo Epoxides
  作者：N. Bhuvaneswari、C.S. Venkatachalam、K.K. Balasubramanian

  DOI：10.1016/s0040-4039(00)91658-7

  日期：1992.3

  The controlled-potential electrolysis of various substituted bromo epoxides in acetonitrile at a mercury pool electrode led to selective reduction of the carbon-bromine bond affording the respective epoxide products in 80-90% yield.