methyl 3-[5-(benzylamino)-5-oxopent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate | 145100-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 3-[5-(benzylamino)-5-oxopent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 145100-08-9
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: JMSPVQOKJOPNQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  668.0±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[5-(benzylamino)-5-oxopent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以73%的产率得到methyl 3-[(1-benzyl-5-oxopyrrolidin-2-ylidene)methyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome

  摘要：

  Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.

  DOI：

  10.1021/jo970289b
• 作为产物：
  描述：

  methyl 4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 methyl 3-[5-(benzylamino)-5-oxopent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome

  摘要：

  Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.

  DOI：

  10.1021/jo970289b

文献信息

• Tetrapyrroles. IV. A highly efficient synthesis of homochiral dihydropyrromethenones via Pdo mediated coupling of iodopyrroles and acetylenic amides
  作者：Peter A. Jacobi、S. Rajeswari

  DOI：10.1016/s0040-4039(00)60941-3

  日期：1992.10

  Homochiral dihydropyrromethenones of type 20 have been synthesized in a highly efficient manner by Pd(o) mediated coupling of iodopyrrole 14 with acetylenic amides 18, followed by F- catalyzed 5-exo-dig cyclization. In analogous fashion, phytochrome (8) precursor 25a has been prepared in 85% overall yield from iodopyrrole 22.