3-acetoxymethyl-3,3a,5,6,7,8-hexahydro-6,6,8-trimethyl-4H-cycloheptaisoxazole | 155934-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-acetoxymethyl-3,3a,5,6,7,8-hexahydro-6,6,8-trimethyl-4H-cycloheptaisoxazole
• 英文别名: (6,6,8-Trimethyl-3,3a,4,5,7,8-hexahydrocyclohepta[c][1,2]oxazol-3-yl)methyl acetate
• CAS: 155934-12-6
• 化学式: C₁₄H₂₃NO₃
• 分子量: 253.342
• InChiKey: SSLDBNMDGNENBI-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±34.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxymethyl-3,3a,5,6,7,8-hexahydro-6,6,8-trimethyl-4H-cycloheptaisoxazole 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以88%的产率得到3,3a,5,6,7,8-hexahydro-3-hydroxymethyl-6,6,8-trimethyl-4H-cycloheptaisoxazole
  参考文献：
  名称：

  Fused Furan Construction via an Intramolecular [3+2] Cycloaddition Reaction: Syntheses of 4H-Cyclohepta- and 4H-Cyclopenta[b]furans

  摘要：

  General and efficient syntheses of 4H-cyclohepta- and 4H-cyclopenta[b]furans (4 and 5) have been accomplished employing the intramolecular [3+2] dipolar cycloaddition based fused furan construction strategy. Treatment of the oximes (20 and 29), readily prepared from the carboxylic acid (7 and 23) via a conventional sequence of reactions, with aqueous sodium hypochlorite produced excellent yields of the isoxazolines (21 and 30), which, after alkaline hydrolysis or desilylation, were exposed to the conditions of reductive hydrolysis followed by acid-catalyzed cyclization to give the corresponding fused furans (4 and 5) in good overall yields.

  DOI：

  10.3987/com-93-6623
• 作为产物：
  描述：

  (E)-1-acetoxy-9-hydroxyimino-2-nonene 在 sodium hypochlorite 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以98%的产率得到3-acetoxymethyl-3,3a,5,6,7,8-hexahydro-6,6,8-trimethyl-4H-cycloheptaisoxazole
  参考文献：
  名称：

  Fused Furan Construction via an Intramolecular [3+2] Cycloaddition Reaction: Syntheses of 4H-Cyclohepta- and 4H-Cyclopenta[b]furans

  摘要：

  General and efficient syntheses of 4H-cyclohepta- and 4H-cyclopenta[b]furans (4 and 5) have been accomplished employing the intramolecular [3+2] dipolar cycloaddition based fused furan construction strategy. Treatment of the oximes (20 and 29), readily prepared from the carboxylic acid (7 and 23) via a conventional sequence of reactions, with aqueous sodium hypochlorite produced excellent yields of the isoxazolines (21 and 30), which, after alkaline hydrolysis or desilylation, were exposed to the conditions of reductive hydrolysis followed by acid-catalyzed cyclization to give the corresponding fused furans (4 and 5) in good overall yields.

  DOI：

  10.3987/com-93-6623