(1R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclohex-3-enecarboxylic acid methyl ester | 142036-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclohex-3-enecarboxylic acid methyl ester
• CAS: 142036-64-4
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: DTHVCWRJHBSOOD-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 、 1,3-丁二烯 反应 17.0h， 以58%的产率得到methyl (1S,2R)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-4-cyclohexen-1-ylcarboxylate
  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