4-[5-(Carbamoyloxymethyl)-2-methyl-4-methylidene-3-oxocyclopenten-1-yl]butyl acetate | 1254569-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-[5-(Carbamoyloxymethyl)-2-methyl-4-methylidene-3-oxocyclopenten-1-yl]butyl acetate
• CAS: 1254569-11-3
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: UBROVAHPDJZEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[5-(Carbamoyloxymethyl)-2-methyl-4-methylidene-3-oxocyclopenten-1-yl]butyl acetate 在 rhodium(II) acetate dimer 、 magnesium oxide 、 iodobenzene diacetate 作用下， 以 甲苯 为溶剂， 反应 0.6h， 以80%的产率得到4-(8-Methyl-6-methylidene-2,7-dioxo-3-oxa-1-azaspiro[4.4]non-8-en-9-yl)butyl acetate
  参考文献：
  名称：

  Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization

  摘要：

  A synthetic study of the Stemona alkaloid stemonamide is described. The FeCl(3)-promoted fast Nazarov reaction of beta-alkoxy divinyl ketones in the presence of t-BuOH afforded an alpha-methylene cyclopentenone, which was subsequently subjected to the Rh-catalyzed C-H amination to provide a fully appropriately substituted alpha-methylene cyclopentenone as the core skeleton of stemonamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.032
• 作为产物：
  描述：

  [2-(4-Hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以99%的产率得到4-[5-(Carbamoyloxymethyl)-2-methyl-4-methylidene-3-oxocyclopenten-1-yl]butyl acetate
  参考文献：
  名称：

  Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization

  摘要：

  A synthetic study of the Stemona alkaloid stemonamide is described. The FeCl(3)-promoted fast Nazarov reaction of beta-alkoxy divinyl ketones in the presence of t-BuOH afforded an alpha-methylene cyclopentenone, which was subsequently subjected to the Rh-catalyzed C-H amination to provide a fully appropriately substituted alpha-methylene cyclopentenone as the core skeleton of stemonamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.032