2-<2-(3-indolyl)ethyl>-3,4-dihydroisochinolin-2H(1)-one | 158195-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-<2-(3-indolyl)ethyl>-3,4-dihydroisochinolin-2H(1)-one
• 英文别名: 2-[2-(1H-indol-3-yl)ethyl]-3,4-dihydroisoquinolin-1-one
• CAS: 158195-12-1
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: VDDLIOKLURMUFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-<2-(3-indolyl)ethyl>-3,4-dihydroisochinolin-2H(1)-one 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 生成 5,6,7,8,13,13b-hexahydrobenzindolo<2,3-h>quinolizine
  参考文献：
  名称：

  Indoles XI. Syntheses and Stereochemistry of 5,6,7,8,13,13b-Hexahydrobenz[a]indolo[2,3-h]quinolizines and of 5,6,7,8,13,13b-Hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine

  摘要：

  A new and efficient synthesis of substituted 5,6,7,8,13,]3b-hexahydro-benz[a]indolo[2,3-h]quinolizines (5b,d) via lactamisation of dihydropyrano[3,4-b]indol-1-one (3), cyclisation with phosphorus oxychloride and reduction with sodium borohydride is described. The unsubstituted 5,6,7,8,13,13b-hexahydro benz[a]indolo[2,3-h]quinolizine (5) is prepared by analogy starting with the lactamisation of isochromanone with tryptamine. The unsubstituted 5,6,7,8,13,13b-hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine (9) is synthesized by lactamisafion of 3 with tryptamine, cyclisation and again reduction of the intermediate immonium salt. The stereochemistry of the unsubstituted quinolizine derivatives is investigated by H-1-, C-13-nmr-, NOE spectroscopy and by X-ray analysis.

  DOI：

  10.3987/com-93-6527
• 作为产物：
  描述：

  异色满 在 selenium(IV) oxide 、 molecular sieve 作用下， 以 xylene 为溶剂， 生成 2-<2-(3-indolyl)ethyl>-3,4-dihydroisochinolin-2H(1)-one
  参考文献：
  名称：

  Indoles XI. Syntheses and Stereochemistry of 5,6,7,8,13,13b-Hexahydrobenz[a]indolo[2,3-h]quinolizines and of 5,6,7,8,13,13b-Hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine

  摘要：

  A new and efficient synthesis of substituted 5,6,7,8,13,]3b-hexahydro-benz[a]indolo[2,3-h]quinolizines (5b,d) via lactamisation of dihydropyrano[3,4-b]indol-1-one (3), cyclisation with phosphorus oxychloride and reduction with sodium borohydride is described. The unsubstituted 5,6,7,8,13,13b-hexahydro benz[a]indolo[2,3-h]quinolizine (5) is prepared by analogy starting with the lactamisation of isochromanone with tryptamine. The unsubstituted 5,6,7,8,13,13b-hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine (9) is synthesized by lactamisafion of 3 with tryptamine, cyclisation and again reduction of the intermediate immonium salt. The stereochemistry of the unsubstituted quinolizine derivatives is investigated by H-1-, C-13-nmr-, NOE spectroscopy and by X-ray analysis.

  DOI：

  10.3987/com-93-6527

文献信息

• Indoles XI. Syntheses and Stereochemistry of 5,6,7,8,13,13b-Hexahydrobenz[a]indolo[2,3-h]quinolizines and of 5,6,7,8,13,13b-Hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine
  作者：Jochen Lehmann、Martin Nieger、Thomas Witt

  DOI：10.3987/com-93-6527

  日期：——

  A new and efficient synthesis of substituted 5,6,7,8,13,]3b-hexahydro-benz[a]indolo[2,3-h]quinolizines (5b,d) via lactamisation of dihydropyrano[3,4-b]indol-1-one (3), cyclisation with phosphorus oxychloride and reduction with sodium borohydride is described. The unsubstituted 5,6,7,8,13,13b-hexahydro benz[a]indolo[2,3-h]quinolizine (5) is prepared by analogy starting with the lactamisation of isochromanone with tryptamine. The unsubstituted 5,6,7,8,13,13b-hexahydro-14H-bisindolo[3,2-a][2,3-h]quinolizine (9) is synthesized by lactamisafion of 3 with tryptamine, cyclisation and again reduction of the intermediate immonium salt. The stereochemistry of the unsubstituted quinolizine derivatives is investigated by H-1-, C-13-nmr-, NOE spectroscopy and by X-ray analysis.