ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate | 503624-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate
• CAS: 503624-12-2
• 化学式: C₁₁H₁₄Br₂O₃
• 分子量: 354.038
• InChiKey: ATXWWOMYVORNAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate 在 potassium phosphate 、 四(三苯基膦)钯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 51.0h， 生成 ethyl 5-bromo-4-(1',3'-dioxolan-2'-yl)-1-methyl-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  Regiospecific substitution of the carbon–boron bond of tris(4-trimethylsilylfuran-3-yl)boroxine and tris(4-methylfuran-3-yl)boroxine. Model approaches towards sesquiterpenoid furanoeudesmanes

  摘要：

  Furan-containing compounds occur abundantly in nature. Among them, the sesquiterpenoid furanoeudesmanes are particularly interesting due to their allergenic, plant-growth inhibiting, antibacterial as well as antitumor properties. Recently an organoboron protocol has been developed in our laboratory for the preparation of regiospecific-substituted furans. By utilizing such methodology, two common intermediates 1 and 2 that may lead to the synthesis of naturally occurring tubipofuran (3) furanoeudesm-4-ene (4) and furanoeudesma-1,4-dien-6-one (5) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01519-3
• 作为产物：
  描述：

  ethyl 1,2-dimethyl-4-oxocyclohex-2-ene-1-carboxylate 在 pyridinium hydrobromide perbromide 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以80%的产率得到ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  Regiospecific substitution of the carbon–boron bond of tris(4-trimethylsilylfuran-3-yl)boroxine and tris(4-methylfuran-3-yl)boroxine. Model approaches towards sesquiterpenoid furanoeudesmanes

  摘要：

  Furan-containing compounds occur abundantly in nature. Among them, the sesquiterpenoid furanoeudesmanes are particularly interesting due to their allergenic, plant-growth inhibiting, antibacterial as well as antitumor properties. Recently an organoboron protocol has been developed in our laboratory for the preparation of regiospecific-substituted furans. By utilizing such methodology, two common intermediates 1 and 2 that may lead to the synthesis of naturally occurring tubipofuran (3) furanoeudesm-4-ene (4) and furanoeudesma-1,4-dien-6-one (5) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01519-3