N,N,1'-triethyl-3',4'-dioxospiro[1,3-dioxane-2,8'-6,7,8a,9-tetrahydrofuro[3,4-f]indolizine]-1'-carboxamide | 785807-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N,1'-triethyl-3',4'-dioxospiro[1,3-dioxane-2,8'-6,7,8a,9-tetrahydrofuro[3,4-f]indolizine]-1'-carboxamide
• CAS: 785807-21-8
• 化学式: C₂₀H₂₈N₂O₆
• 分子量: 392.452
• InChiKey: NGDKBCGGYUJCNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N,1'-triethyl-3',4'-dioxospiro[1,3-dioxane-2,8'-6,7,8a,9-tetrahydrofuro[3,4-f]indolizine]-1'-carboxamide 在 N-溴代丁二酰亚胺(NBS) 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 23.0h， 生成 N,N,1-triethyl-3,4,8-trioxo-6,7-dihydrofuro[3,4-f]indolizine-1-carboxamide
  参考文献：
  名称：

  Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety

  摘要：

  A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye 2 with tricylclic ketone 3 affords camptothecin after further elaboration. Tricyclic ketone 3 is prepared via a route employing a [3+2] nitrone cyclo-addition and an intramolecular Knoevenagel condensation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.025
• 作为产物：
  描述：

  N,N-diethyl-2-hydroxy-2-spiro[1,3-dioxane-2,4'-3,3a,5,6-tetrahydro-2H-pyrrolo[1,2-b][1,2]oxazole]-2'-ylbutanamide 在 potassium tert-butylate 、 溶剂黄146 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 N,N,1'-triethyl-3',4'-dioxospiro[1,3-dioxane-2,8'-6,7,8a,9-tetrahydrofuro[3,4-f]indolizine]-1'-carboxamide
  参考文献：
  名称：

  Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety

  摘要：

  A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye 2 with tricylclic ketone 3 affords camptothecin after further elaboration. Tricyclic ketone 3 is prepared via a route employing a [3+2] nitrone cyclo-addition and an intramolecular Knoevenagel condensation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.025

文献信息

• Synthesis of (±)-camptothecin using a [3+2] nitrone cycloaddition to construct the CDE ring moiety
  作者：Jurong Yu、Jeffrey DePue、David Kronenthal

  DOI：10.1016/j.tetlet.2004.08.025

  日期：2004.9

  A novel synthesis to camptothecin is described. A Friedlander condensation of o-aminobenzaldehye 2 with tricylclic ketone 3 affords camptothecin after further elaboration. Tricyclic ketone 3 is prepared via a route employing a [3+2] nitrone cyclo-addition and an intramolecular Knoevenagel condensation. (C) 2004 Elsevier Ltd. All rights reserved.