methyl 4,5-dihydro[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one-2-carboxylate | 208335-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 4,5-dihydro[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one-2-carboxylate
• 英文别名: Methyl 11-oxo-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,15(19),16-hexaene-17-carboxylate
• CAS: 208335-72-2
• 化学式: C₁₈H₁₃NO₅
• 分子量: 323.305
• InChiKey: NTRZKOPBGXJUIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4,5-dihydro[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one-2-carboxylate 在 氢氧化钾 、 copper bronze 作用下， 以 喹啉 、 甲醇 为溶剂， 反应 2.75h， 生成 去氢石蒜碱酮
  参考文献：
  名称：

  利用1,3,4-恶二唑的连续分子内Diels-Alder反应全合成脱水可乐酮。

  摘要：

  详细介绍了聚合的脱水氢化可可酮的合成过程，包括适当取代的2-氨基-1,3,4-恶二唑的分子内Diels-Alder反应，定义了新的恶二唑->呋喃->苯Diels-Alder策略。

  DOI：

  10.1021/jo020437k
• 作为产物：
  描述：

  6-溴苯并[d][1,3]二氧代-5-羧酸 在 吡啶 、 草酰氯 、 lithium perchlorate 、 六正丁基二锡 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 89.0h， 生成 methyl 4,5-dihydro[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one-2-carboxylate
  参考文献：
  名称：

  IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids

  摘要：

  Acylation of 5-amino-2-furancarboxylic acid methyl ester with alkenoyl acid chlorides gives 2-amidofurans that undergo intramolecular Diels-Alder cycloadditions. The reactions occur at 165 degrees C in toluene or at 100 degrees C when 4 M ethereal LiClO4 was used as the solvent. The resultant dihydroindoles are formed by the nitrogen lone pair assisted ring opening of the initial era-bridged cycloadducts, followed by loss of water. Under certain conditions, alternative cationic cyclization routes become important pathways. Several members of the pyrrolophenanthridine class of alkaloids were obtained by a short, efficient method based on the intramolecular Diels-Alder furan cycloaddition of 2-amidofurans containing a tethered alkenyl group. The resulting dihydroindoles were elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system by a free radical induced cyclization using bis(tributyltin).

  DOI：

  10.1021/jo980008f

文献信息

• IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids
  作者：Albert Padwa、Martin Dimitroff、Alex G. Waterson、Tianhua Wu

  DOI：10.1021/jo980008f

  日期：1998.6.1

  Acylation of 5-amino-2-furancarboxylic acid methyl ester with alkenoyl acid chlorides gives 2-amidofurans that undergo intramolecular Diels-Alder cycloadditions. The reactions occur at 165 degrees C in toluene or at 100 degrees C when 4 M ethereal LiClO4 was used as the solvent. The resultant dihydroindoles are formed by the nitrogen lone pair assisted ring opening of the initial era-bridged cycloadducts, followed by loss of water. Under certain conditions, alternative cationic cyclization routes become important pathways. Several members of the pyrrolophenanthridine class of alkaloids were obtained by a short, efficient method based on the intramolecular Diels-Alder furan cycloaddition of 2-amidofurans containing a tethered alkenyl group. The resulting dihydroindoles were elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system by a free radical induced cyclization using bis(tributyltin).
• Total Synthesis of Anhydrolycorinone Utilizing Sequential Intramolecular Diels−Alder Reactions of a 1,3,4-Oxadiazole
  作者：Scott E. Wolkenberg、Dale L. Boger

  DOI：10.1021/jo020437k

  日期：2002.10.1

  A convergent total synthesis of anhydrolycorinone is detailed, enlisting sequential intramolecular Diels-Alder reactions of a suitably substituted 2-amino-1,3,4-oxadiazole defining a novel oxadiazole --> furan --> benzene Diels-Alder strategy.

  详细介绍了聚合的脱水氢化可可酮的合成过程，包括适当取代的2-氨基-1,3,4-恶二唑的分子内Diels-Alder反应，定义了新的恶二唑->呋喃->苯Diels-Alder策略。