diethyl 4-benzyl-2,3,4,6-tetrahydro[1,4]oxazino[2,3-f]indole-2,7-dicarboxylate | 462117-26-6

• 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: diethyl 4-benzyl-2,3,4,6-tetrahydro[1,4]oxazino[2,3-f]indole-2,7-dicarboxylate
• 英文别名: 2,7-diethyl 4-benzyl-2H,3H,4H,6H-indolo[5,6-b][1,4]oxazine-2,7-dicarboxylate；diethyl 4-benzyl-3,6-dihydro-2H-pyrrolo[2,3-g][1,4]benzoxazine-2,7-dicarboxylate
• CAS: 462117-26-6
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: KYXMKMNDDCSXEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-benzyl-2,3,4,6-tetrahydro[1,4]oxazino[2,3-f]indole-2,7-dicarboxylate 在 苄基三甲基氢氧化铵 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 diethyl 11-benzyl-1-oxo-1,2,3,9,10,11-hexahydro[1,4]oxazino[3,2-f]pyrrolo[3,2,1-ij]quinoline-5,9-dicarboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of 1,4-Oxazinoindole Derivatives

  摘要：

  Application of the Hemetsberger reaction to ethyl 4-benzyl-7-formyl-2,3-dihydro-1,4-benzoxazine-2-carboxylate (1) or acetate (2) afforded a mixture of ethyl 2,3,4,6-tetrahydro-[1,4]oxazino[2,3-f]indole-7-carboxylate derivatives 3 or 4 and ethyl 2,3,4,9-tetrahydro[1,4]oxazino[3,2-g]indole-8-carboxylate derivatives 5 or 7, with the "linear" derivatives pre-dominant. Michael addition of tert-butyl acrylate to the indole nitrogen atom of 3, 4 and subsequent electrophilic cyclisation gave access to tetracyclic compounds 24, 25, (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200205)2002:10<1646::aid-ejoc1646>3.0.co;2-k
• 作为产物：
  描述：

  ethyl 4-benzyl-7-formyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 xylene 为溶剂， 反应 20.0h， 生成 diethyl 4-benzyl-2,3,4,6-tetrahydro[1,4]oxazino[2,3-f]indole-2,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of 1,4-Oxazinoindole Derivatives

  摘要：

  Application of the Hemetsberger reaction to ethyl 4-benzyl-7-formyl-2,3-dihydro-1,4-benzoxazine-2-carboxylate (1) or acetate (2) afforded a mixture of ethyl 2,3,4,6-tetrahydro-[1,4]oxazino[2,3-f]indole-7-carboxylate derivatives 3 or 4 and ethyl 2,3,4,9-tetrahydro[1,4]oxazino[3,2-g]indole-8-carboxylate derivatives 5 or 7, with the "linear" derivatives pre-dominant. Michael addition of tert-butyl acrylate to the indole nitrogen atom of 3, 4 and subsequent electrophilic cyclisation gave access to tetracyclic compounds 24, 25, (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200205)2002:10<1646::aid-ejoc1646>3.0.co;2-k

文献信息

• Mayer, Stanislas; Joseph, Benoit; Guillaumet, Gerald, Synthesis, 2002, # 13, p. 1871 - 1878
  作者：Mayer, Stanislas、Joseph, Benoit、Guillaumet, Gerald、Merour, Jean-Yves

  DOI：——

  日期：——
• Synthesis and Reactivity of 1,4-Oxazinoindole Derivatives
  作者：Stanislas Mayer、Jean-Yves Mérour、Benoît Joseph、Gérald Guillaumet

  DOI：10.1002/1099-0690(200205)2002:10<1646::aid-ejoc1646>3.0.co;2-k

  日期：2002.5

  Application of the Hemetsberger reaction to ethyl 4-benzyl-7-formyl-2,3-dihydro-1,4-benzoxazine-2-carboxylate (1) or acetate (2) afforded a mixture of ethyl 2,3,4,6-tetrahydro-[1,4]oxazino[2,3-f]indole-7-carboxylate derivatives 3 or 4 and ethyl 2,3,4,9-tetrahydro[1,4]oxazino[3,2-g]indole-8-carboxylate derivatives 5 or 7, with the "linear" derivatives pre-dominant. Michael addition of tert-butyl acrylate to the indole nitrogen atom of 3, 4 and subsequent electrophilic cyclisation gave access to tetracyclic compounds 24, 25, (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.