2-[(2-溴-4-氯苯氧基)甲基]环氧乙烷 | 68224-01-1

• 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-氯苯氧基)甲基]环氧乙烷
• 英文名称: 2-((2-bromo-4-chlorophenoxy)methyl)oxirane
• 英文别名: 2-(2-Bromo-4-chlorophenoxymethyl)oxirane；2-[(2-bromo-4-chlorophenoxy)methyl]oxirane
• CAS: 68224-01-1
• 化学式: C₉H₈BrClO₂
• mdl: MFCD09737731
• 分子量: 263.518
• InChiKey: UYDDEAYCMGCKPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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-氯苯氧基)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88%的产率得到4-氯苯基缩水甘油醚
  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-氯苯酚 、 环氧溴丙烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 24.0h， 生成 2-[(2-溴-4-氯苯氧基)甲基]环氧乙烷
  参考文献：
  名称：

  铜催化的环氧化物与有机硼化合物的交叉偶联反应。

  摘要：

  描述了铜与芳基硼酸酯的铜催化的交叉偶联反应。该反应不限于芳族环氧化物，因为脂族环氧化物也是合适的底物。另外，N-磺酰基氮丙啶可以成功地转化为产物。该反应可方便地获得作为有价值的合成中间体的β-苯乙醇。

  DOI：

  10.1039/c4cc09321f

文献信息

• Copper-catalyzed cross-coupling reactions of epoxides with gem-diborylmethane: access to γ-hydroxyl boronic esters
  作者：Ahmed Ebrahim-Alkhalil、Zhen-Qi Zhang、Tian-Jun Gong、Wei Su、Xiao-Yu Lu、Bin Xiao、Yao Fu

  DOI：10.1039/c5cc09817c

  日期：——

  Herein, we describe a novel copper-catalyzed epoxide opening reaction with gem-diborylmethane.

  在本文中，我们描述了与宝石-二硼烷基甲烷的新型铜催化的环氧化物开环反应。
• 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.
• DE1236523
  申请人：——

  公开号：——

  公开（公告）日：——
• 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：——
• Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
  作者：Xiao-Yu Lu、Chu-Ting Yang、Jing-Hui Liu、Zheng-Qi Zhang、Xi Lu、Xin Lou、Bin Xiao、Yao Fu

  DOI：10.1039/c4cc09321f

  日期：——

  A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to beta-phenethyl alcohols, which are valuable synthetic intermediates.

  描述了铜与芳基硼酸酯的铜催化的交叉偶联反应。该反应不限于芳族环氧化物，因为脂族环氧化物也是合适的底物。另外，N-磺酰基氮丙啶可以成功地转化为产物。该反应可方便地获得作为有价值的合成中间体的β-苯乙醇。