methyl 3-[(3R,4R)-5-amino-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate | 145100-12-5

• 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-[(3R,4R)-5-amino-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pent-1-ynyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
• CAS: 145100-12-5
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: LBJAKDKATNNFSK-AOIWGVFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.41
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[(3R,4R)-5-amino-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pent-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， 以75%的产率得到methyl 3-[(Z)-[(3R,4R)-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pyrrolidin-2-ylidene]methyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Tetrapyrroles. IV. A highly efficient synthesis of homochiral dihydropyrromethenones via Pdo mediated coupling of iodopyrroles and acetylenic amides

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60941-3
• 作为产物：
  描述：

  在 copper(l) iodide 、 四(三苯基膦)钯 、 氨 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 methyl 3-[(3R,4R)-5-amino-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pent-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