methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxopropionate | 188053-99-8

• 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-oxopropionate
• 英文别名: methyl 2-(1,3-dioxoisoindol-2-yl)-3-hydroxyprop-2-enoate
• CAS: 188053-99-8
• 化学式: C₁₂H₉NO₅
• 分子量: 247.207
• InChiKey: NQQLPGGFXFKRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 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：
  0.08
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxopropionate 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 175.0h， 生成 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：

  甲酸甲酯 、 2-邻苯二甲酰亚胺基乙酸甲酯 在 sodium 作用下， 反应 18.0h， 以80%的产率得到methyl 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxopropionate
  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

文献信息

• An Efficient Enantioselective Synthesis of Strigolactones with a Palladium-Catalyzed Asymmetric Coupling as the Key Step
  作者：Anat Reizelman、Binne Zwanenburg

  DOI：10.1002/1099-0690(200203)2002:5<810::aid-ejoc810>3.0.co;2-u

  日期：2002.3

  An efficient enantioselective methodology for the preparation of the strigolactones GR7, GR24 and Nijmegen-1 based on palladium-catalyzed asymmetric coupling has been developed, The products are obtained in good yield and high optical purity. This Methodology is an attractive alternative for installing the stereochemisry at C2' of the D-ring. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).