α-n-Butyl-β-hydroxy-γ-valerolakton | 34867-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-n-Butyl-β-hydroxy-γ-valerolakton
• 英文别名: (4R,5S)-3-butyl-4-hydroxy-5-methyloxolan-2-one
• CAS: 34867-17-9；37676-49-6；42246-61-7；42246-62-8；42246-64-0；42246-65-1；53402-76-9；56297-89-3；56297-90-6；57572-77-7；86900-11-0；90410-19-8；90694-66-9；98673-33-7；110612-43-6；147922-91-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: LLALEXXCKCFLES-PPSBICQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-n-Butyl-β-hydroxy-γ-valerolakton 、 异戊酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到(+)-blastmycinone
  参考文献：
  名称：

  Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

  摘要：

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

  DOI：

  10.1021/ol503246k

文献信息

• Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide
  作者：Santosh J. Gharpure、Laxmi Narayan Nanda、Manoj Kumar Shukla

  DOI：10.1021/ol503246k

  日期：2014.12.19

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.