(1S,3R,4S)-2-Benzyl-1-isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 141812-89-7

• 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: (1S,3R,4S)-2-Benzyl-1-isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• CAS: 141812-89-7
• 化学式: C₂₅H₃₀N₂O₂
• 分子量: 390.525
• InChiKey: XYWKMWVHXCVNDG-CODAWKSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S)-2-Benzyl-1-isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以79%的产率得到(1S,3R,4S)-1-Isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereospecific Synthesis of trans, cis-1,3,4-Trisubstituted 1,2,3,4-Tetrahydro-b-Carbolines

  摘要：

  Pictet-Spengler condensation of N(bb)-benzyl-beta-methyltryptophan methyl ester (2RS,3SR;4) with aldehydes followed by debenzylation afforded trans, cis-1,3,4-trisubstituted 1,2,3,4-tetrahydro-beta-carbolines in complete stereospecific fashion. Tetrahydro-beta-carbolines (6a) and (6b) were prepared by the direct condensation of beta-methyltryptophan methyl ester (4) with the corresponding aldehydes. The stereochemistry of the products was confirmed by an X-ray analysis of 6a.

  DOI：

  10.3987/com-91-5912
• 作为产物：
  描述：

  β-methyltryptophan methyl ester, 2RS,3SR isomer 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 12.5h， 生成 (1S,3R,4S)-2-Benzyl-1-isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereospecific Synthesis of trans, cis-1,3,4-Trisubstituted 1,2,3,4-Tetrahydro-b-Carbolines

  摘要：

  Pictet-Spengler condensation of N(bb)-benzyl-beta-methyltryptophan methyl ester (2RS,3SR;4) with aldehydes followed by debenzylation afforded trans, cis-1,3,4-trisubstituted 1,2,3,4-tetrahydro-beta-carbolines in complete stereospecific fashion. Tetrahydro-beta-carbolines (6a) and (6b) were prepared by the direct condensation of beta-methyltryptophan methyl ester (4) with the corresponding aldehydes. The stereochemistry of the products was confirmed by an X-ray analysis of 6a.

  DOI：

  10.3987/com-91-5912