3-benzo[1,3]dioxol-5-yl-1-[5-(2-hydroxyethoxymethyl)furan-2-yl]prop-2-yn-1-ol | 784193-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-benzo[1,3]dioxol-5-yl-1-[5-(2-hydroxyethoxymethyl)furan-2-yl]prop-2-yn-1-ol
• CAS: 784193-67-5
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: IUMCOBAIKGNIMN-UHFFFAOYSA-N

物化性质

• 沸点：
  486.9±45.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.29
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-benzo[1,3]dioxol-5-yl-1-[5-(2-hydroxyethoxymethyl)furan-2-yl]prop-2-yn-1-ol 在 copper(II) sulfate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 (Z)-2-(3-benzo[1,3]dioxol-5-ylprop-2-ynylidene)-1,6,9-trioxaspiro[4.5]dec-3-ene 、 (E)-2-(3-benzo[1,3]dioxol-5-ylprop-2-ynylidene)-1,6,9-trioxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  Synthesis and Antifeeding Activities of Tonghaosu Analogues

  摘要：

  Tonghaosu (1), a lead for a botanical antifeedant, and its 22 analogues were synthesized according to a previously reported concise and straightforward procedure. The structures of all new compounds were confirmed by NMR, IR, MS, and HREIMS or elemental analysis. Their insect antifeedant activities against the large white butterfly (Pieris brassicae L.) were examined, and six analogues (Z- and E-6h and Z-isomers of 6i-I), which contain 1,3-diyn or 3,4-methylenedioxyphenyl acetylene group, showed considerable antifeedant activity. Interestingly, Zisomers of 6i-k are much more active than their corresponding E-isomers.

  DOI：

  10.1021/jf049479v
• 作为产物：
  描述：

  acetic acid 2-[5-(3-benzo[1,3]dioxol-5-yl-1-hydroxyprop-2-ynyl)furan-2-ylmethoxy]ethyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以91%的产率得到3-benzo[1,3]dioxol-5-yl-1-[5-(2-hydroxyethoxymethyl)furan-2-yl]prop-2-yn-1-ol
  参考文献：
  名称：

  Synthesis and Antifeeding Activities of Tonghaosu Analogues

  摘要：

  Tonghaosu (1), a lead for a botanical antifeedant, and its 22 analogues were synthesized according to a previously reported concise and straightforward procedure. The structures of all new compounds were confirmed by NMR, IR, MS, and HREIMS or elemental analysis. Their insect antifeedant activities against the large white butterfly (Pieris brassicae L.) were examined, and six analogues (Z- and E-6h and Z-isomers of 6i-I), which contain 1,3-diyn or 3,4-methylenedioxyphenyl acetylene group, showed considerable antifeedant activity. Interestingly, Zisomers of 6i-k are much more active than their corresponding E-isomers.

  DOI：

  10.1021/jf049479v