methyl 7-acetoxy-3,4,4',5'-tetrahydro-5-pentylspiro[2H-1-benzopyran-2,2'(3'H)-furan]-8-carboxylate | 942057-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 7-acetoxy-3,4,4',5'-tetrahydro-5-pentylspiro[2H-1-benzopyran-2,2'(3'H)-furan]-8-carboxylate
• CAS: 942057-52-5
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: IDNNDOBSFBWGJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 7-acetoxy-3,4,4',5'-tetrahydro-5-pentylspiro[2H-1-benzopyran-2,2'(3'H)-furan]-8-carboxylate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到methyl 3,4,4',5'-tetrahydro-7-hydroxy-5-pentylspiro[2H-1-benzopyran-2,2'(3'H)-furan]-8-carboxylate
  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：

  3,5-二羟基戊苯 在 potassium hydrogencarbonate 作用下， 以 甘油 为溶剂， 反应 5.0h， 生成 methyl 7-acetoxy-3,4,4',5'-tetrahydro-5-pentylspiro[2H-1-benzopyran-2,2'(3'H)-furan]-8-carboxylate
  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