methyl 4-ethoxy-5-phenoxypentanoate | 182416-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-ethoxy-5-phenoxypentanoate
• CAS: 182416-57-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: WEZAWUFIBHLXKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-ethoxy-5-phenoxypentanoate 在 p-nitrobenzenesulfonyl azide 、 辛酸铑 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.83h， 生成 methyl (R^*,R^*,R^*)-2-methyl-5-(phenoxymethyl)-2,3,4,5-tetrahydro-3-furancarboxylate
  参考文献：
  名称：

  Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans

  摘要：

  Dirhodium(II) carboxylate catalyzed cyclization of a series of gamma-alkoxy-alpha-diazo esters 1 has been shown to proceed with substantial diastereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2 and 3. The diastereoselectivity of the cyclization improved as the electron-withdrawing ability of the substituent R increased. A mechanistic hypothesis is presented.

  DOI：

  10.1021/jo960758u
• 作为产物：
  描述：

  1-phenoxy-5-hexen-2-ol 在 sodium hydroxide 、 四丁基碘化铵 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 paraffin 为溶剂， 反应 5.0h， 生成 methyl 4-ethoxy-5-phenoxypentanoate
  参考文献：
  名称：

  Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans

  摘要：

  Dirhodium(II) carboxylate catalyzed cyclization of a series of gamma-alkoxy-alpha-diazo esters 1 has been shown to proceed with substantial diastereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2 and 3. The diastereoselectivity of the cyclization improved as the electron-withdrawing ability of the substituent R increased. A mechanistic hypothesis is presented.

  DOI：

  10.1021/jo960758u

文献信息

• 2,3,5-trisubstituted tetrahydrofurans by Rh-mediated cyclization of an α-diazo ester
  作者：Douglass F. Taber、Ying Song

  DOI：10.1016/0040-4039(95)00346-e

  日期：1995.4

  Dirhodium(II) carboxylate catalyzed cyclization of a gamma-alkoxy-alpha-diazo ester 1 was found to proceed with substantial diasatereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2a and 2b in a ratio of 4 : 1.
• Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans
  作者：Douglass F. Taber、Ying Song

  DOI：10.1021/jo960758u

  日期：1996.1.1

  Dirhodium(II) carboxylate catalyzed cyclization of a series of gamma-alkoxy-alpha-diazo esters 1 has been shown to proceed with substantial diastereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2 and 3. The diastereoselectivity of the cyclization improved as the electron-withdrawing ability of the substituent R increased. A mechanistic hypothesis is presented.