(2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid | 647830-62-4

• 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: (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid
• 英文别名: 3-Furancarboxylic acid, tetrahydro-4-methyl-2-octyl-5-oxo-, (2S,3R,4R)-；(2S,3R,4R)-4-methyl-2-octyl-5-oxooxolane-3-carboxylic acid
• CAS: 647830-62-4
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: GQYYQVFYWKFMBP-GRYCIOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid 、 丙烯胺 在 tris(2-oxo-3-oxazolinyl)phosphine oxide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以51%的产率得到(2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid allylamide
  参考文献：
  名称：

  New α-methylene-γ-butyrolactones with antimycobacterial properties

  摘要：

  The synthesis and antimyco bacterial activity of a series of alpha-methylene-gamma-butyrolactones based on the natural product protolichesterinic acid are described. Compounds 9-12 bearing an allylamide group at the C-4 position showed improved activity with MICs in the range of 6.25-12.5 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.119
• 作为产物：
  描述：

  C75 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (2S,3R,4S)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid 、 (2S,3R,4R)-4-Methyl-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid
  参考文献：
  名称：

  New α-methylene-γ-butyrolactones with antimycobacterial properties

  摘要：

  The synthesis and antimyco bacterial activity of a series of alpha-methylene-gamma-butyrolactones based on the natural product protolichesterinic acid are described. Compounds 9-12 bearing an allylamide group at the C-4 position showed improved activity with MICs in the range of 6.25-12.5 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.119

文献信息

• New α-methylene-γ-butyrolactones with antimycobacterial properties
  作者：Minerva A. Hughes、Jill M. McFadden、Craig A. Townsend

  DOI：10.1016/j.bmcl.2005.05.119

  日期：2005.9

  The synthesis and antimyco bacterial activity of a series of alpha-methylene-gamma-butyrolactones based on the natural product protolichesterinic acid are described. Compounds 9-12 bearing an allylamide group at the C-4 position showed improved activity with MICs in the range of 6.25-12.5 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.