2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole | 153000-65-8

• 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: 2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole
• 英文别名: methyl 2-[3-[2-(benzylamino)ethyl]-1H-indol-2-yl]acetate
• CAS: 153000-65-8
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: PMMQQMBQOSOBCT-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±45.0 °C(predicted)
• 密度：
  1.178±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 三氟化硼乙醚 、 甲酸铵 作用下， 以 甲醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 97.25h， 生成 19-(Benzylthio)akuammicine
  参考文献：
  名称：

  Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 6. Total Syntheses of (.+-.)-Echitamidine, (.+-.)-Alstogustine, (.+-.)-19-epi-Alstogustine, and (.+-.)-Akuammicine

  摘要：

  19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25% overall yield based on a new condensation-sigmatropic rearrangement sequence. Reductions-and quaternization reactions furnished the title compounds.

  DOI：

  10.1021/jo00104a042
• 作为产物：
  描述：

  Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以87%的产率得到2-<(methoxycarbonyl)methyl>-3-<2-(N^b-benzylamino)ethyl>indole
  参考文献：
  名称：

  Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates

  摘要：

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.

  DOI：

  10.1021/jo00078a029

文献信息

• Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 9.¹ The Enantioselective Generation of Tetracyclic ABCE Intermediates by a Tandem Condensation, [3,3]-Sigmatropic Rearrangement, and Cyclization Sequence
  作者：Martin E. Kuehne、Feng Xu

  DOI：10.1021/jo970207j

  日期：1997.11.1

  tryptophan-derived benzyl 2-(benzylamino)-3-[3-[2-[(methoxycarbonyl)methyl]indolyl]]propionate gave tetracyclic hexahydro-1H-pyrrolo[2,3-d] intermediates with stereoselective placement of substituents for cyclization to pentacyclic Strychnos alkaloids. The benzyl ester moiety was readily removed by formation of a corresponding nitrile and reduction, thus providing enantioselective syntheses of the tetracyclic

  取代的丙烯醛与色氨酸衍生的苄基2-（苄氨基）-3- [3- [2-[（[甲氧羰基甲基]吲哚基]吲哚基]]丙酸酯的反应得到四环六氢-1H-吡咯并[2,3-d]中间体取代基的立体选择性放置，以环化成五环马兜铃生物碱。通过形成相应的腈并还原，可以容易地除去苄基酯部分，从而提供四环化合物的对映选择性合成。
• Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 11. Total Syntheses of (−)-Lochneridine and (−)- and Racemic 20-<i>epi</i>-Lochneridine
  作者：Martin E. Kuehne、Feng Xu

  DOI：10.1021/jo981401o

  日期：1998.12.1

  Enantioselective syntheses of (-)-lochneridine (1) and (-)-epi-lochneridine (2) were obtained by two alternative C-20 diastereoselective syntheses of the respective pentacyclic (3aS,5S,11bR)-methyl 12-oxo-3,5-ethano-2,3,3a,4,5,7-hexahydro-3H-pyrrolo[2,3-d]carbazole-6-carboxylate ((-)-8) and tetracyclic methyl (2S,3aS,5R,11bR))-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo[2,3d]carbazole-6-carboxylate ((-)-12b) precursors from tryptophan derived 2-[(methoxycarbonyl)methyl]3-[2(S)-(methoxy or benzyloxycarbonyl)-2-(N-b-benzyl)aminoethyl]indole (15 or 16). While a modified Grignard reaction of the ketone (-)-8 provided (-)-lochneridine (1), dihydroxylation and cyclization of the olefin (-)-12b gave its C-20 epimer (2).
• Total synthesis of strychnan and aspidospermatan alkaloids. 3. The total synthesis of (.+-.)-strychnine
  作者：Martin E. Kuehne、Feng Xu

  DOI：10.1021/jo00078a030

  日期：1993.12

  Reaction of N(b)-benzyl-2-[(methoxycarbonyl)methyl]tryptamine (3) with 4,4-dimethoxybut-2-en-1-al (6) provided, by a new condensation-electrocyclization reaction, the tetracyclic core 2 of strychnine (1). A 13-step elaboration of this compound gave a stereoselective synthesis of the racemic alkaloid.
• Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates
  作者：Rodney L. Parsons、Jeffrey D. Berk、Martin E. Kuehne

  DOI：10.1021/jo00078a029

  日期：1993.12

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.
• Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 6. Total Syntheses of (.+-.)-Echitamidine, (.+-.)-Alstogustine, (.+-.)-19-epi-Alstogustine, and (.+-.)-Akuammicine
  作者：Martin E. Kuehne、Feng Xu、Christopher S. Brook

  DOI：10.1021/jo00104a042

  日期：1994.12

  19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25% overall yield based on a new condensation-sigmatropic rearrangement sequence. Reductions-and quaternization reactions furnished the title compounds.