(3aR,7aR)-3a,7a-dihydro-2,2-dimethyl-3a-[(2-propenyloxy)methyl]-1,3-benzodioxole | 778629-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,7aR)-3a,7a-dihydro-2,2-dimethyl-3a-[(2-propenyloxy)methyl]-1,3-benzodioxole
• 英文别名: (3aR,7aR)-2,2-dimethyl-7a-(prop-2-enoxymethyl)-3aH-1,3-benzodioxole
• CAS: 778629-64-4
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: GHLJOVFXPRBKMR-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-3a,7a-dihydro-2,2-dimethyl-3a-[(2-propenyloxy)methyl]-1,3-benzodioxole 反应 3.33h， 以94%的产率得到[3aR-(3aα,4β,6aα,7β,10aα)]-3a,4,7,8-tetrahydro-2,2,-dimethyl-4,7-methano-6aH,10H-[1,3]-dioxole-[4,5-i][2]benzopyran
  参考文献：
  名称：

  Microwave-mediated intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives

  摘要：

  The synthetic utility of biodihydroxylated benzoic acid derivatives for the construction of bridge bicyclo scaffolds was investigated. Biodihydroxylation of benzoic acid using Ralstonia eutropha B9 gave (IS,2R)-1,2-dihydroxycyclobexa-3,5-diene-1-carboxylic acid (DCD) in high optical purity (>95% ee). Protection of the intermediate and subsequent functional group transformation gave the required cyclization precursors in moderate to excellent overall yields. Subsequent intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives was carried out using either thermal or microwave conditions. Enantiomerically pure products with five chiral centers were obtained in 4-6 steps from achiral starting material. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.109
• 作为产物：
  描述：

  (1S,6R)-1,6-二羟基环己-2,4-二烯-1-羧酸 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 0.33h， 生成 (3aR,7aR)-3a,7a-dihydro-2,2-dimethyl-3a-[(2-propenyloxy)methyl]-1,3-benzodioxole
  参考文献：
  名称：

  Microwave-mediated intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives

  摘要：

  The synthetic utility of biodihydroxylated benzoic acid derivatives for the construction of bridge bicyclo scaffolds was investigated. Biodihydroxylation of benzoic acid using Ralstonia eutropha B9 gave (IS,2R)-1,2-dihydroxycyclobexa-3,5-diene-1-carboxylic acid (DCD) in high optical purity (>95% ee). Protection of the intermediate and subsequent functional group transformation gave the required cyclization precursors in moderate to excellent overall yields. Subsequent intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives was carried out using either thermal or microwave conditions. Enantiomerically pure products with five chiral centers were obtained in 4-6 steps from achiral starting material. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.109

文献信息

• Intramolecular Diels–Alder cyclization of biodihydroxylated benzoic acid derivatives towards novel heterocyclic scaffolds
  作者：Thomas C. M. Fischer、Hannes G. Leisch、Marko D. Mihovilovic

  DOI：10.1007/s00706-010-0291-7

  日期：2010.6

  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.