(1S,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0^2.6)-8-decen-3-one | 115237-16-6

• 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: (1S,2S,5S,6R,7R)-5-hydroxymethyl-4-oxatricyclo(5.2.1.0^2.6)-8-decen-3-one
• 英文别名: (1S,2S,5S,6R,7R)-5-(hydroxymethyl)-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 115237-16-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: URUODEXMTMJWQS-ABRLLLAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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 (1S,2S,3R,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 在 盐酸 、 甲醇 作用下， 以85%的产率得到(1S,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

文献信息

• Diastereofacial selectivity in uncatalyzed Diels-Alder cycloadditions involving α,β-unsaturated esters and lactones with stereogenic centers containing oxygen functiionalities
  作者：Ramón Casas、Teodor Parella、Vicenç Branchadell、Antonio Oliva、Rosa M. Ortuño、André Guingant

  DOI：10.1016/s0040-4020(01)88527-6

  日期：1992.3

  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.