(2R,5S,8S)-2,5-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione | 204980-47-2

• 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: (2R,5S,8S)-2,5-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• CAS: 204980-47-2
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: QOLRWTHVQCSGTH-RWEMILLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5S,8S)-2,5-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1R,12S,15R)-12,15-dimethyl-3,11,14,17-tetrazahexacyclo[12.11.0.02,11.04,9.016,24.018,23]pentacosa-2,4,6,8,16(24),18,20,22-octaene-10,13-dione
  参考文献：
  名称：

  Stereochemical issues related to the synthesis of 7,10-dimethyl-7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones

  摘要：

  Condensation reactions between anthranilic acid and iminoethers derived from 2,3,6,7,12,12a-hexahydropyrazino[1,2-b]beta-carboline-1,4-diones 3-8 to give the title hexacyclic compounds were studied from a stereochemical point of view. The configuration was retained in the formation of iminoethers, but inversion of the tryptophan sterocenter C-16a took place in the condensation process. Epimerization also occurred in an alternative procedure that involves acylation at N-2 with o-azidobenzoyl chloride, followed by intramolecular aza-Wittig reaction. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00315-2
• 作为产物：
  描述：

  (3S)-cis-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester; hydrochloride 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.5h， 生成 (2R,5S,8S)-2,5-dimethyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
  参考文献：
  名称：

  立体控制合成3,6-二甲基-2,3,6,7,12,12a-六氢吡嗪并[1,2-b]-β-咔啉-1,4-二酮。

  摘要：

  DOI：

  10.1021/jo971842s

文献信息

• Stereochemical issues related to the synthesis of 7,10-dimethyl-7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones
  作者：Antonio Madrigal、Mercedes Grande、Carmen Avendaño

  DOI：10.1016/s0957-4166(98)00315-2

  日期：1998.9

  Condensation reactions between anthranilic acid and iminoethers derived from 2,3,6,7,12,12a-hexahydropyrazino[1,2-b]beta-carboline-1,4-diones 3-8 to give the title hexacyclic compounds were studied from a stereochemical point of view. The configuration was retained in the formation of iminoethers, but inversion of the tryptophan sterocenter C-16a took place in the condensation process. Epimerization also occurred in an alternative procedure that involves acylation at N-2 with o-azidobenzoyl chloride, followed by intramolecular aza-Wittig reaction. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Stereocontrolled Synthesis of 3,6-Dimethyl- 2,3,6,7,12,12a-hexahydropyrazino[1,2-<i>b</i>]-β- carboline-1,4-diones
  作者：Antonio Madrigal、Mercedes Grande、Carmen Avendaño

  DOI：10.1021/jo971842s

  日期：1998.4.1