methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(6(R)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(S)-yloxy)acrylate | 188054-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(6(R)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(S)-yloxy)acrylate
• CAS: 188054-01-5
• 化学式: C₂₂H₁₉NO₇
• 分子量: 409.395
• InChiKey: VEGUALKMTZGSCK-JTLCLONHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(6(R)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(S)-yloxy)acrylate 以 邻二氯苯 为溶剂， 反应 7.0h， 以31%的产率得到methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(4-methyl-5-oxo-2,5-dihydrofuran-2(S)-yloxy)acrylate
  参考文献：
  名称：

  Synthesis of a Phthaloylglycine-Derived Strigol Analogue and Its Germination Stimulatory Activity toward Seeds of the Parasitic Weeds Striga hermonthica and Orobanche crenata

  摘要：

  The newly designed strigol analogue Nijmegen 1 (rac 7) was prepared in high overall yield starting from N-phthaloylglycine, This relatively simple analogue exhibits high bioactivity in the stimulation of germination of seeds of the parasitic weeds Striga hermonthica and Orobanche crenata. Nijmegen 1 was resolved in its enantiomers 7 and ent 7 by using the homochiral latent D-rings ent 11 and ent 12. The enantiomers 7 and ent 7 show significant differences in germination activity.

  DOI：

  10.1021/jf9604504
• 作为产物：
  描述：

  2-邻苯二甲酰亚胺基乙酸甲酯 在 potassium tert-butylate 、 sodium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 186.0h， 生成 methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(6(R)-methyl-5-oxo-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3(S)-yloxy)acrylate
  参考文献：
  名称：

  Synthesis of a Phthaloylglycine-Derived Strigol Analogue and Its Germination Stimulatory Activity toward Seeds of the Parasitic Weeds Striga hermonthica and Orobanche crenata

  摘要：

  The newly designed strigol analogue Nijmegen 1 (rac 7) was prepared in high overall yield starting from N-phthaloylglycine, This relatively simple analogue exhibits high bioactivity in the stimulation of germination of seeds of the parasitic weeds Striga hermonthica and Orobanche crenata. Nijmegen 1 was resolved in its enantiomers 7 and ent 7 by using the homochiral latent D-rings ent 11 and ent 12. The enantiomers 7 and ent 7 show significant differences in germination activity.

  DOI：

  10.1021/jf9604504