3,4-dimethyl-4-phenyl-3-methoxycarbonyl-γ-butyrolactone | 1494623-30-1

• 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: 3,4-dimethyl-4-phenyl-3-methoxycarbonyl-γ-butyrolactone
• CAS: 1494623-30-1
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: LWVGZQYBLKCTPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  衣康酸二甲酯 、 苯乙酮 在 三氟乙酸 、 cobalt(II) bromide 、 锌 作用下， 以 1,2-二溴乙烷 、 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到3,4-dimethyl-4-phenyl-3-methoxycarbonyl-γ-butyrolactone
  参考文献：
  名称：

  Microwave-Assisted Synthesis and Antileishmanial Activity of 3-methoxycarbonyl-γ-butyrolactone Derivatives

  摘要：

  We describe the microwave-assisted synthesis of ten 3-methoxycarbonyl-gamma-butyrolactone derivatives and evaluate their in vitro antileishmanial activity against promastigote forms of Leishmania amazonensis. The synthesis furnished most of the compounds in 80-95% yield and reactions lasted about 10-20 min. Most of the compounds displayed IC50 values higher than 400 mu M. Compounds 5 (trans-3-(p-methoxy) benzyl-4-methyl-3-methoxycarbonyl-gamma-butyrolactone) and 10 (trans-3-(pmethoxy) benzyl-4-benzyl-3-methoxycarbonyl-gamma-butyrolactone) were the exceptions: they displayed IC50 values of 170.4 and 179.6 M, respectively, suggesting that the leishmanicidal activity of 3-methoxycarbonyl-gamma-butyrolactones may be related to the nature and size of the substituent at position C-4.

  DOI：

  10.5935/0103-5053.20140113

文献信息

• Microwave-Assisted Synthesis and Antileishmanial Activity of 3-methoxycarbonyl-γ-butyrolactone Derivatives
  作者：Marcos F. Pinatto-Botelho、Antonio E. M. Crotti、Julia M. de Souza、Lizandra G. Magalhães、Paulo M. Donate

  DOI：10.5935/0103-5053.20140113

  日期：——

  We describe the microwave-assisted synthesis of ten 3-methoxycarbonyl-gamma-butyrolactone derivatives and evaluate their in vitro antileishmanial activity against promastigote forms of Leishmania amazonensis. The synthesis furnished most of the compounds in 80-95% yield and reactions lasted about 10-20 min. Most of the compounds displayed IC50 values higher than 400 mu M. Compounds 5 (trans-3-(p-methoxy) benzyl-4-methyl-3-methoxycarbonyl-gamma-butyrolactone) and 10 (trans-3-(pmethoxy) benzyl-4-benzyl-3-methoxycarbonyl-gamma-butyrolactone) were the exceptions: they displayed IC50 values of 170.4 and 179.6 M, respectively, suggesting that the leishmanicidal activity of 3-methoxycarbonyl-gamma-butyrolactones may be related to the nature and size of the substituent at position C-4.