(1R,2S,6R,7S)-2-hydroxy-7-hydroxymethyl-8-oxabicyclo(4.3.0)-3-nonen-9-one | 141985-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2S,6R,7S)-2-hydroxy-7-hydroxymethyl-8-oxabicyclo(4.3.0)-3-nonen-9-one
• 英文别名: (3S,3aR,7S,7aR)-7-hydroxy-3-(hydroxymethyl)-3a,4,7,7a-tetrahydro-3H-2-benzofuran-1-one
• CAS: 141985-63-9
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: GOWIPDDNWGNILB-RULNZFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl (1R,2R,6S)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-6-trimethylsilyloxy-4-cyclohexen-1-ylcarboxylate 在 盐酸 、 甲醇 作用下， 以77%的产率得到(1R,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0^2.6)-8-decen-3-one
  参考文献：
  名称：

  Diastereofacial selectivity in uncatalyzed Diels-Alder cycloadditions involving α,β-unsaturated esters and lactones with stereogenic centers containing oxygen functiionalities

  摘要：

  Both experimental and theoretical studies on the Diels-Alder cycloadditions of dienophiles 1, 2 and 3 to different dienes show that the observed diastereofacial selectivity results from a combination of electronic and steric interactions. The traditional Felkin-Anh model is not appropriate for these cases. Several new chiral synthetic building blocks have been prepared.

  DOI：

  10.1016/s0040-4020(01)88527-6