N-(1-formyl-2-(1H-indol-3-yl)ethyl)benzamide | 484652-86-0

• 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: N-(1-formyl-2-(1H-indol-3-yl)ethyl)benzamide
• 英文别名: N-[1-(1H-indol-3-yl)-3-oxopropan-2-yl]benzamide
• CAS: 484652-86-0
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: YPUJULLBSSSNMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.96
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(1-formyl-2-(1H-indol-3-yl)ethyl)benzamide 在 硝酸铵 、 氢氧化钾 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 二氯甲烷 、 二乙二醇 为溶剂， 反应 17.5h， 生成 3-(3,3-diethoxy-2-methoxycarbonylamino-propyl)indol-1-carbonic acid methyl ester
  参考文献：
  名称：

  Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines

  摘要：

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.

  DOI：

  10.1007/s007060200071
• 作为产物：
  描述：

  rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(1-formyl-2-(1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines

  摘要：

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.

  DOI：

  10.1007/s007060200071

文献信息

• Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines
  作者：Eberhard Reimann、Wolfgang Erdle、Eugen Hargasser、Hermann Lotter

  DOI：10.1007/s007060200071

  日期：2002.7

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.