ethyl 1-methyl-4-oxo-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate | 503624-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-methyl-4-oxo-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate
• 英文别名: Ethyl 1-methyl-4-oxo-2-[(4-trimethylsilylfuran-3-yl)methyl]cyclohex-2-ene-1-carboxylate；ethyl 1-methyl-4-oxo-2-[(4-trimethylsilylfuran-3-yl)methyl]cyclohex-2-ene-1-carboxylate
• CAS: 503624-16-6
• 化学式: C₁₈H₂₆O₄Si
• 分子量: 334.488
• InChiKey: WCIMBNVWKXVMKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-4-oxo-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以92%的产率得到ethyl 1-methyl-4-hydroxy-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 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 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 53.5h， 生成 ethyl 1-methyl-4-oxo-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

文献信息

• 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
  作者：Chung-Yan Yick、Tsun-Keung Tsang、Henry N.C Wong

  DOI：10.1016/s0040-4020(02)01519-3

  日期：2003.1

  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.