methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylate | 1369262-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylate
• 英文别名: Methyl (4r,6r)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-encarboxylate；methyl (4R,6R)-6-hydroxy-4-prop-1-en-2-ylcyclohexene-1-carboxylate
• CAS: 1369262-56-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: ZHTVTOLXLFDNPS-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-carboxylate 在 锌 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以67%的产率得到methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Chiral cyclohexene block from R-(−)-carvone

  摘要：

  The oxidation with SeO2 of a methyl group linked to an sp(2)-hybridized carbon in the product of the intramolecular iodoetherification of cis-carveol afforded (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]-oct-3-en-4-carbaldehyde and [(1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-yl]methanol that were oxidized to methyl (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-carboxylate. The latter by the Zn-promoted opening of the gamma-oxide ring was converted into the target chiral block, methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-encarboxylate.

  DOI：

  10.1134/s1070428012020054