methyl (1S,2R,3S,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate | 142036-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1S,2R,3S,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate
• 英文别名: methyl (1S,2R,3S,4R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 142036-73-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: USDBKQWWJZGXCN-VSSNEEPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 、 环戊二烯 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.7h， 生成 methyl (1R,2S,3R,4S)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 、 methyl (1S,2S,3R,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate 、 methyl (1S,2R,3S,4R)-3-<(4S)-4-(2,2-dimethyl-1,3-dioxolo)>bicyclo(2.2.1)-5-hepten-2-ylcarboxylate
  参考文献：
  名称：

  路易斯酸催化环戊二烯在（E）-和（Z）-（S）-4,5-二-O-异亚丙基-2-戊烯酸甲酯上的Diels-Alder加成反应：速率和立体选择性。

  摘要：

  Rate, and endo/exo and facial diastereostereoselectivity of the title reactions have been highly enhanced under the action of aluminum, among other metals used as catalysts, compared to the thermal processes. EtAlCl2 and Et2AlCl were the reagents that afforded the best results.

  DOI：

  10.1016/s0957-4166(00)82295-8

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.
• Lewis acid catalyzed Diels-Alder additions of cyclopentadiene to methyl (E)- and (Z)-(S)-4,5-di-O-isopropylidenepent-2-enoates: Rate and stereoselectivity.
  作者：Zhiyu Chen、Rosa M. Ortun˜o

  DOI：10.1016/s0957-4166(00)82295-8

  日期：1992.5

  Rate, and endo/exo and facial diastereostereoselectivity of the title reactions have been highly enhanced under the action of aluminum, among other metals used as catalysts, compared to the thermal processes. EtAlCl2 and Et2AlCl were the reagents that afforded the best results.