Tert-butyl 2-(2-methoxyoxolan-2-yl)acetate | 942057-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tert-butyl 2-(2-methoxyoxolan-2-yl)acetate
• 英文别名: tert-butyl 2-(2-methoxyoxolan-2-yl)acetate
• CAS: 942057-41-2
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: HLMXNFFXZNWUBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-(2-methoxyoxolan-2-yl)acetate 在 二异丁基氢化铝 、 rochelle salt 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.5h， 生成 2-(2-methoxyoxolan-2-yl)acetic acid
  参考文献：
  名称：

  Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid

  摘要：

  Acid-catalyzed condensation of 2,6-dihydroxybenzoic acid 3 with ketal aldehyde 14 in methanol at 25 degrees C, followed by CH2N2 esterification, gave a 4: 1: 4: 1 mixture of diastereomers 15b-18b in 60% yield. Equilibration of this mixture with TFA in CDCI3 provided tetracycle 15b ( 83% yield) with the complete skeleton of berkelic acid. A similar condensation at 0 degrees C afforded 15b - 18b and a reduction product 19b, which was probably formed by a 1,5-hydride shift.

  DOI：

  10.1021/ol0704338
• 作为产物：
  描述：

  tert-butyl 2-(2-hydroxytetrahydrofuran-2-yl)acetate 在 Dowex 50WX₈-400-(H+) resin 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以1.28 g的产率得到Tert-butyl 2-(2-methoxyoxolan-2-yl)acetate
  参考文献：
  名称：

  Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid

  摘要：

  Acid-catalyzed condensation of 2,6-dihydroxybenzoic acid 3 with ketal aldehyde 14 in methanol at 25 degrees C, followed by CH2N2 esterification, gave a 4: 1: 4: 1 mixture of diastereomers 15b-18b in 60% yield. Equilibration of this mixture with TFA in CDCI3 provided tetracycle 15b ( 83% yield) with the complete skeleton of berkelic acid. A similar condensation at 0 degrees C afforded 15b - 18b and a reduction product 19b, which was probably formed by a 1,5-hydride shift.

  DOI：

  10.1021/ol0704338

文献信息

• Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid
  作者：Jingye Zhou、Barry B. Snider

  DOI：10.1021/ol0704338

  日期：2007.5.1

  Acid-catalyzed condensation of 2,6-dihydroxybenzoic acid 3 with ketal aldehyde 14 in methanol at 25 degrees C, followed by CH2N2 esterification, gave a 4: 1: 4: 1 mixture of diastereomers 15b-18b in 60% yield. Equilibration of this mixture with TFA in CDCI3 provided tetracycle 15b ( 83% yield) with the complete skeleton of berkelic acid. A similar condensation at 0 degrees C afforded 15b - 18b and a reduction product 19b, which was probably formed by a 1,5-hydride shift.