methyl (1R,2R,6S)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-6-trimethylsilyloxy-4-cyclohexen-1-ylcarboxylate | 141985-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2R,6S)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-6-trimethylsilyloxy-4-cyclohexen-1-ylcarboxylate
• CAS: 141985-56-0
• 化学式: C₁₆H₂₈O₅Si
• 分子量: 328.481
• InChiKey: VNIBTLKVCFMKHB-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(trimethylsiloxy)-1,3-butadiene 、 methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 40.0 ℃ 、1199.99 MPa 条件下， 反应 64.0h， 以100%的产率得到methyl (1R,2R,6S)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-6-trimethylsilyloxy-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