(5S,2'S,5'S)-2-(bismethoxymethylpyrrolidinyl)carbonyl-4,5-dimethyl-5H-furan-2-one | 240118-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5S,2'S,5'S)-2-(bismethoxymethylpyrrolidinyl)carbonyl-4,5-dimethyl-5H-furan-2-one
• 英文别名: (5S)-5-[(2S,5S)-2,5-bis(methoxymethyl)pyrrolidine-1-carbonyl]-4,5-dimethylfuran-2-one
• CAS: 240118-45-0
• 化学式: C₁₅H₂₃NO₅
• 分子量: 297.351
• InChiKey: PPILQTXSXQIUCD-HUBLWGQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,2'S,5'S)-2-(bismethoxymethylpyrrolidinyl)carbonyl-4,5-dimethyl-5H-furan-2-one 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以83%的产率得到(4S,5S,2'S,5'S)-5-(bismethoxymethylpyrrolidinyl)carbonyl-4,5-dimethyldihydrofuran-2-one
  参考文献：
  名称：

  The synthesis of (−)-cis- and (−)-trans-crobarbatic acid

  摘要：

  The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00097-x
• 作为产物：
  描述：

  3-甲基-2-糠酸 在 chromium(VI) oxide 、 sodium hydroxide 、 氯化亚砜 、 硫酸 、 氨 、 sodium 、 天然橡胶 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.17h， 生成 (5S,2'S,5'S)-2-(bismethoxymethylpyrrolidinyl)carbonyl-4,5-dimethyl-5H-furan-2-one
  参考文献：
  名称：

  The synthesis of (−)-cis- and (−)-trans-crobarbatic acid

  摘要：

  The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00097-x