(3aS,7aR)-2,2-Dimethyl-7aH-benzo[1,3]dioxole-3a-carboxylic acid allylamide | 778629-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,7aR)-2,2-Dimethyl-7aH-benzo[1,3]dioxole-3a-carboxylic acid allylamide
• CAS: 778629-68-8
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: WSJFMFJCLWEEKR-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-2,2-Dimethyl-7aH-benzo[1,3]dioxole-3a-carboxylic acid allylamide 反应 8.33h， 以28%的产率得到[3aR-(3aα,4β,6aα,7β,10aα)]-3a,4,6a,7,8,9-hexahydro-2,2-dimethyl-4,7-methano-10H-[1,3]dioxole-[4,5-i]isochinolin-10-one
  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 1-羟基苯并三唑 、 对甲苯磺酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (3aS,7aR)-2,2-Dimethyl-7aH-benzo[1,3]dioxole-3a-carboxylic acid allylamide
  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