5,6-dimethyldihydropyran-2,4-dione | 338386-56-4

• 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: 5,6-dimethyldihydropyran-2,4-dione
• 英文别名: rel-(5R,6S)-Dihydro-5,6-dimethyl-2H-pyran-2,4(3H)-dione；(5R,6S)-5,6-dimethyloxane-2,4-dione
• CAS: 338386-56-4
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: SGPLFZCZLSOZJX-UHNVWZDZSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  289.8±33.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛 、 丙酰乙酸乙酯 在 正丁基锂 、 sodium hydride 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 2.5h， 生成 5,6-dimethyldihydropyran-2,4-dione 、 5,6-dimethyldihydropyran-2,4-dione
  参考文献：
  名称：

  Synthesis and evaluation of the molluscicidal activity of the 5,6-dimethyl-dihydro-pyran-2,4-dione and 6-substituted analogous

  摘要：

  Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4-dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H2O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0degreesC). The 5,6-dimethyl-dihydro-piran-2,4-dione and three analogous dihydro-piran-2,4-diones 6-substituted,-phenyl, (4-methoxy-phenyl), and -propenyl, showed significant activities against the Biomphalaria glabrata egg masses, while the analogous 6-(3,4-dimethoxy-phenyl) was inactive as molluscicide. This activity is reported for the first time, extending the range of biological activities of this group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.001