3-(Hydroxymethyl)-5-propyloxolan-2-one | 295796-51-9

• 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: 3-(Hydroxymethyl)-5-propyloxolan-2-one
• 英文别名: 3-(hydroxymethyl)-5-propyloxolan-2-one
• CAS: 295796-51-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HHQAULQCXVNYAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3-(Hydroxymethyl)-5-propyloxolan-2-one 在 吡啶 作用下， 反应 6.0h， 生成 3-methylene-5-propyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and Biological Activity of α-Methylene-γ-lactones as New Aroma Chemicals

  摘要：

  Seven kinds of alpha -methylene-gamma -lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha -methylene-gamma -lactones had characteristic and unique odors. All alpha -methylene-gamma -lactones added a roast-like odor to materials. The antimicrobial effects of alpha -methylene-gamma -lactones were investigated by using a paper disk diffusion method. The results showed the alpha -methylene-gamma -lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha -methylene-gamma -undecalactone and alpha -methylene-gamma -dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha -methylene-gamma -lactones suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by alpha -methylene-gamma -lactones had a tendency to intensify as the number of carbons in the side chain increased.

  DOI：

  10.1021/jf000346t
• 作为产物：
  描述：

  丙位庚内酯 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 3-(Hydroxymethyl)-5-propyloxolan-2-one
  参考文献：
  名称：

  Synthesis and Biological Activity of α-Methylene-γ-lactones as New Aroma Chemicals

  摘要：

  Seven kinds of alpha -methylene-gamma -lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha -methylene-gamma -lactones had characteristic and unique odors. All alpha -methylene-gamma -lactones added a roast-like odor to materials. The antimicrobial effects of alpha -methylene-gamma -lactones were investigated by using a paper disk diffusion method. The results showed the alpha -methylene-gamma -lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha -methylene-gamma -undecalactone and alpha -methylene-gamma -dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha -methylene-gamma -lactones suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by alpha -methylene-gamma -lactones had a tendency to intensify as the number of carbons in the side chain increased.

  DOI：

  10.1021/jf000346t

文献信息

• Synthesis and Biological Activity of α-Methylene-γ-lactones as New Aroma Chemicals
  作者：Mitsuo Miyazawa、Hiroshi Shimabayashi、Shuichi Hayashi、Seiji Hashimoto、Sei-ichi Nakamura、Hiroshi Kosaka、Hiromu Kameoka

  DOI：10.1021/jf000346t

  日期：2000.11.1

  Seven kinds of alpha -methylene-gamma -lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha -methylene-gamma -lactones had characteristic and unique odors. All alpha -methylene-gamma -lactones added a roast-like odor to materials. The antimicrobial effects of alpha -methylene-gamma -lactones were investigated by using a paper disk diffusion method. The results showed the alpha -methylene-gamma -lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha -methylene-gamma -undecalactone and alpha -methylene-gamma -dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha -methylene-gamma -lactones suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by alpha -methylene-gamma -lactones had a tendency to intensify as the number of carbons in the side chain increased.