methyl (1S,2R)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-4-cyclohexen-1-ylcarboxylate | 141985-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S,2R)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-4-cyclohexen-1-ylcarboxylate
• CAS: 141985-55-9
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: DTHVCWRJHBSOOD-OUAUKWLOSA-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

• 作为反应物：
  描述：

  methyl (1S,2R)-2-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>-4-cyclohexen-1-ylcarboxylate 在 盐酸 、 甲醇 作用下， 以99%的产率得到(1S,6R,7S)-7-hydroxymethyl-8-oxabicyclo(4.3.0)-3-nonen-9-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：

  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

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.