(3S,5aR,10bS,11aS)-6-Acetyl-1-ethoxy-3-methyl-3,5a,6,10b,11,11a-hexahydro-pyrazino[1',2':1,5]pyrrolo[2,3-b]indol-4-one | 216165-04-7

• 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: (3S,5aR,10bS,11aS)-6-Acetyl-1-ethoxy-3-methyl-3,5a,6,10b,11,11a-hexahydro-pyrazino[1',2':1,5]pyrrolo[2,3-b]indol-4-one
• 英文别名: (1R,4S,7S,9S)-16-acetyl-6-ethoxy-4-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-5,10,12,14-tetraen-3-one
• CAS: 216165-04-7
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: FLQFXXZXSQUWAU-MSMFTSAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氨基苯甲酸 、 (3S,5aR,10bS,11aS)-6-Acetyl-1-ethoxy-3-methyl-3,5a,6,10b,11,11a-hexahydro-pyrazino[1',2':1,5]pyrrolo[2,3-b]indol-4-one 反应 0.05h， 以41%的产率得到(1S,12S,15R,23S)-16-acetyl-12-methyl-3,11,14,16-tetrazahexacyclo[12.10.0.02,11.04,9.015,23.017,22]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione
  参考文献：
  名称：

  Solvent-Free Cyclocondensation of Lactim Ethers with Anthranilic Acid under Microwave Irradiation

  摘要：

  微波辐射极大地改善了邻氨基苯甲酸与2,5-哌嗪二酮衍生的内酰亚胺之间的环缩合反应时​​间、产率和立构中心完整性，从而生成吡嗪并[2,1-b]喹唑啉-3,6-二酮。当应用于双内酰亚胺醚时，微波辅助反应也比热反应好得多，导致在优良的收率，同时也改进了抗MDR天然产物N-乙酰葆明含环体系​​化合物的制备。

  DOI：

  10.1055/s-2004-817784
• 作为产物：
  描述：

  triethyloxonium fluoroborate 、 (1R,4S,7S,9S)-16-acetyl-4-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到(3S,5aR,10bS,11aS)-6-Acetyl-1-ethoxy-3-methyl-3,5a,6,10b,11,11a-hexahydro-pyrazino[1',2':1,5]pyrrolo[2,3-b]indol-4-one
  参考文献：
  名称：

  On the fate of the tryptophan stereocenter during the synthesis of hexacyclic analogues of N-acetylardeemin

  摘要：

  The reaction between 6-acetyl-3-alkyl-1-ethoxy-3,4,5a,6, 11,11a-hexahydro-10bH-pyrazino-[2 ',1 '-5,1]pyrrolo[2,3-b]indole-l,4-diones and anthranilic acid was studied from a stereochemical point of view. Various degrees of epimerization of the tryptophan and alanine stereocenters were observed in compounds with a cis relationship between their H-3 and H-11a hydrogen atoms, and stereochemistry was retained in the trans compounds. These observations are explained in terms of steric compression between the C-5=O, C-7-alkyl and C-8=O groups in the hexacyclic reaction products. Acylation at N-2 with o-azidobenzoyl chloride followed by an intramolecular aza Wittig reaction afforded the target 10-acetyl-5,7,8,9a, 10,14b, 15,15a-octahydroindolo[3 ",2 "-4 ',5 ']pyrrolo[2 ',1 '-3,4]pyrazino[2,1-b]quinazoline-5,8-diones with retention of all stereocenters. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00307-3

文献信息

• Microwave-Assisted, Solvent-Free Synthesis of Several Quinazoline Alkaloid Frameworks
  作者：J. Menéndez、Pilar Cledera、Juan Sánchez、Esmeralda Caballero、Tamara Yates、Elena Ramírez、Carmen Avendaño、M. Ramos

  DOI：10.1055/s-2007-990818

  日期：2007.11

  Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to prepare some derivatives of the pyrazino[2,1-b]quinazoline-3,6-dione system present in many quinazoline alkaloids. It could also be applied to the synthesis of compounds containing the complete hexacyclic ring system of the anti-MDR natural product N-acetyl­ardeemin, and other comprising the pentacyclic framework of circumdatin E. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino[2,1-b:5,4-b′]diquinazoline-8,16-dione in excellent yield.

  微波辐照显著改善了邻氨基苯甲酸与来自哌嗪-2,5-二酮的乳酰亚胺醚之间的环加成反应，在反应时间、产率和立体中心完整性方面均有显著提升。该反应已被用于制备多种喹唑啉生物碱中存在的吡嗪并[2,1-b]喹唑啉-3,6-二酮系统的衍生物。它还可以应用于合成含有抗多药耐药天然产物N-乙酰基阿德米宁的完整六环体系化合物，以及其他包含circumdatin E的五环框架的化合物。微波辅助反应在应用于双乳酰亚胺醚时也比热反应更为高效，得到了对应的五环吡嗪并[2,1-b:5,4-b′]双喹唑啉-8,16-二酮，产率极佳。