(S)-methyl 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1H-indol-3-yl)propanoate | 1151508-97-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-methyl 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1H-indol-3-yl)propanoate
• 英文别名: methyl (2S)-2-(1,3-dioxo-4H-isoquinolin-2-yl)-3-(1H-indol-3-yl)propanoate
• CAS: 1151508-97-2
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: FWMQYMFHJXBVFS-SFHVURJKSA-N

物化性质

• 沸点：
  626.6±55.0 °C(predicted)
• 密度：
  1.364±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (S)-methyl 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1H-indol-3-yl)propanoate 在 air 、 三乙胺 作用下， 反应 12.0h， 生成 (R)-methyl 2-((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)-1-hydroxy-3-oxoisoindoline-1-carboxylate 、 (S)-methyl 2-((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)-1-hydroxy-3-oxoisoindoline-1-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of (+)-isoindolo-β-carboline

  摘要：

  Starting from homophthalic anhydride and (S)-tryptophan, the stereoselective synthesis of (+)-isoindolo-beta-carboline has been described via the corresponding homophthalimide, its chemoselective oxidative ring contraction, and the intramolecular dehydrative ring closure followed by a geometry-specific demethoxycarbonylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.001
• 作为产物：
  描述：

  (S)-methyl 3-(1H-indol-3-yl)-2-(2-(2-methoxy-2-oxoethyl)benzamido)propanoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到(S)-methyl 2-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Stereoselective synthesis of (+)-isoindolo-β-carboline

  摘要：

  Starting from homophthalic anhydride and (S)-tryptophan, the stereoselective synthesis of (+)-isoindolo-beta-carboline has been described via the corresponding homophthalimide, its chemoselective oxidative ring contraction, and the intramolecular dehydrative ring closure followed by a geometry-specific demethoxycarbonylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.001

文献信息

• Stereoselective synthesis of (+)-isoindolo-β-carboline
  作者：Prasad B. Wakchaure、Vedavati G. Puranik、Narshinha P. Argade

  DOI：10.1016/j.tetasy.2009.01.001

  日期：2009.2

  Starting from homophthalic anhydride and (S)-tryptophan, the stereoselective synthesis of (+)-isoindolo-beta-carboline has been described via the corresponding homophthalimide, its chemoselective oxidative ring contraction, and the intramolecular dehydrative ring closure followed by a geometry-specific demethoxycarbonylation. (C) 2009 Elsevier Ltd. All rights reserved.