(1R,3S)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid | 320589-55-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1R,3S)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid
• 英文别名: (1R,3S)-3-methoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid
• CAS: 320589-55-7
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: FJFZHPXIJLBXRK-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 以 xylene 为溶剂， 反应 2.0h， 以98%的产率得到methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-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：

  乙醛酸 、 L-色氨酸甲酯 以 乙酸乙酯 为溶剂， 反应 16.0h， 以84%的产率得到(1R,3S)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid
  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

文献信息

• MODIFIED PICTET-SPENGLER REACTION AND PRODUCTS PREPARED THEREFROM
  申请人：Lilly ICOS LLC

  公开号：EP1546149B1

  公开（公告）日：2008-11-26
• 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
  作者：Antonio Madrigal、Mercedes Grande、Carmen Avendaño

  DOI：10.1016/s0957-4166(00)00282-2

  日期：2000.9

  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.