methyl (6R,12aS)-1,4-dioxo-2,3,6,7,12,12a-hexahydropyrazino[1,2-a]β-carboline-6-carboxylate | 320589-63-7

• 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: methyl (6R,12aS)-1,4-dioxo-2,3,6,7,12,12a-hexahydropyrazino[1,2-a]β-carboline-6-carboxylate
• 英文别名: methyl (2R,8S)-4,7-dioxo-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-2-carboxylate
• CAS: 320589-63-7
• 化学式: C₁₆H₁₅N₃O₄
• 分子量: 313.313
• InChiKey: RBKFHLDLPQITDD-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (6R,12aS)-1,4-dioxo-2,3,6,7,12,12a-hexahydropyrazino[1,2-a]β-carboline-6-carboxylate 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl (1R,15R)-10,13-dioxo-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-15-carboxylate
  参考文献：
  名称：

  The fate of the tryptophan stereocenter in the synthesis of 7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones

  摘要：

  Condensation reactions of anthranilic acid with iminoethers 14-17 derived from tetracycles 9-13 to give the title hexacyclic compounds reflect a preferred trans-relationship for H(10)-H(16a) protons in C(7)-unsubstituted products and a cis-relatioship for H(7)-H(16a) protons in C(10)-unsubstituted analogs. This synthetic strategy is limited by the steric hindrance of the substituent at C(10). Theoretical calculations are in agreement with the experimental results. The regioselectivity in favor of the linear tetracyclic compound 11 with respect to 12 has also been confirmed. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00282-2
• 作为产物：
  描述：

  dimethyl (1R,3S)-1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 methyl (6R,12aS)-1,4-dioxo-2,3,6,7,12,12a-hexahydropyrazino[1,2-a]β-carboline-6-carboxylate
  参考文献：
  名称：

  The fate of the tryptophan stereocenter in the synthesis of 7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones

  摘要：

  Condensation reactions of anthranilic acid with iminoethers 14-17 derived from tetracycles 9-13 to give the title hexacyclic compounds reflect a preferred trans-relationship for H(10)-H(16a) protons in C(7)-unsubstituted products and a cis-relatioship for H(7)-H(16a) protons in C(10)-unsubstituted analogs. This synthetic strategy is limited by the steric hindrance of the substituent at C(10). Theoretical calculations are in agreement with the experimental results. The regioselectivity in favor of the linear tetracyclic compound 11 with respect to 12 has also been confirmed. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00282-2