[2-(4-Hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate | 1254569-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2-(4-Hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate
• 英文别名: [2-(4-hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate
• CAS: 1254569-09-9
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: HWYAFSWOJUJYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(4-Hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate 在 rhodium(II) acetate dimer 、 magnesium oxide 、 iodobenzene diacetate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以80%的产率得到9-(4-Hydroxybutyl)-8-methyl-6-methylidene-3-oxa-1-azaspiro[4.4]non-8-ene-2,7-dione
  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：

  [3-Methyl-5-methylidene-4-oxo-2-[4-tri(propan-2-yl)silyloxybutyl]cyclopent-2-en-1-yl]methyl carbamate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以97%的产率得到[2-(4-Hydroxybutyl)-3-methyl-5-methylidene-4-oxocyclopent-2-en-1-yl]methyl carbamate
  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

文献信息

• Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization
  作者：Kentaro Yaji、Mitsuru Shindo

  DOI：10.1016/j.tetlet.2010.08.032

  日期：2010.10

  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.