(3aS,7aR)-3a,7a-dihydro-3a-iodomethyl-2,2-dimethyl-1,3-benzodioxole | 1236004-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3aS,7aR)-3a,7a-dihydro-3a-iodomethyl-2,2-dimethyl-1,3-benzodioxole
• 英文别名: (3As,7ar)-3a,7a-dihydro-3a-(iodomethyl)-2,2-dimethyl-1,3-benzodioxole；(3aR,7aS)-7a-(iodomethyl)-2,2-dimethyl-3aH-1,3-benzodioxole
• CAS: 1236004-72-0
• 化学式: C₁₀H₁₃IO₂
• 分子量: 292.117
• InChiKey: LJYZXRJSRWXNIZ-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-3a,7a-dihydro-3a-iodomethyl-2,2-dimethyl-1,3-benzodioxole 、 丙烯胺 反应 36.0h， 以78%的产率得到[3aR-(3aR*,4S*,6aS*,7R*,10aR*)]-4,6a,7,8,9,10-hexahydro-2,2-dimethyl-4,7-methano-3aH-1,3-dioxolo[4,5-i]isoquinoline
  参考文献：
  名称：

  Intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives towards novel heterocyclic scaffolds

  摘要：

  The potential of biodihydroxylated benzoic acid derivatives as versatile precursors for the construction of polycyclic scaffolds was investigated. Ralstonia eutropha B9 was used to biodihydroxylate sodium benzoate to sodium (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate in high optical purity (>95% ee). The required cyclization precursors could be obtained in moderate to excellent yields after protection of the intermediate and subsequent functional group transformation. Intramolecular Diels-Alder cylizations were carried out under thermal or microwave conditions leading to enantiomerically pure products with five chiral centers.

  DOI：

  10.1007/s00706-010-0291-7
• 作为产物：
  描述：

  ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以76%的产率得到(3aS,7aR)-3a,7a-dihydro-3a-iodomethyl-2,2-dimethyl-1,3-benzodioxole
  参考文献：
  名称：

  Intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives towards novel heterocyclic scaffolds

  摘要：

  The potential of biodihydroxylated benzoic acid derivatives as versatile precursors for the construction of polycyclic scaffolds was investigated. Ralstonia eutropha B9 was used to biodihydroxylate sodium benzoate to sodium (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate in high optical purity (>95% ee). The required cyclization precursors could be obtained in moderate to excellent yields after protection of the intermediate and subsequent functional group transformation. Intramolecular Diels-Alder cylizations were carried out under thermal or microwave conditions leading to enantiomerically pure products with five chiral centers.

  DOI：

  10.1007/s00706-010-0291-7