(1S,3S)-2-(2-tert-Butoxycarbonylamino-acetyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 216768-58-0

• 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: (1S,3S)-2-(2-tert-Butoxycarbonylamino-acetyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• CAS: 216768-58-0
• 化学式: C₂₁H₂₇N₃O₅
• 分子量: 401.462
• InChiKey: DXUQDDQOKWYNDV-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  100.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3S)-2-(2-tert-Butoxycarbonylamino-acetyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (1R,15S)-15-methyl-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：

  BOC-甘氨酸 、 methyl (1S,3S)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 calcium chloride 作用下， 反应 24.0h， 以71%的产率得到(1S,3S)-2-(2-tert-Butoxycarbonylamino-acetyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  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