(3S)-2-tert-butyloxycarbonyl-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline | 159979-06-3

• 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: (3S)-2-tert-butyloxycarbonyl-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 2-O-tert-butyl 3-O-methyl (3S)-6-methoxy-1,3,4,9-tetrahydropyrido[3,4-b]indole-2,3-dicarboxylate
• CAS: 159979-06-3
• 化学式: C₁₉H₂₄N₂O₅
• 分子量: 360.41
• InChiKey: FDAIZKIQDUVGMD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-2-tert-butyloxycarbonyl-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline 在 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 对甲苯甲醚 、 溶剂黄146 作用下， 生成 (3'R,5'S)-5-Methoxy-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the oxindole alkaloid (−)-horsfiline

  摘要：

  A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-beta-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the unnatural optical antipode (+)-1, starting from 5-hydroxy-1-tryptophan as the single source from the chiral pool.

  DOI：

  10.1016/s0957-4166(00)86273-4
• 作为产物：
  描述：

  (3S)-2-tert-butyloxycarbonyl-3-carbomethoxy-6-hydroxy-1,2,3,4-tetrahydro-β-carboline 、 三甲基硅烷化重氮甲烷 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 18.0h， 以96%的产率得到(3S)-2-tert-butyloxycarbonyl-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Synthesis of the oxindole alkaloid (−)-horsfiline

  摘要：

  A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-beta-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the unnatural optical antipode (+)-1, starting from 5-hydroxy-1-tryptophan as the single source from the chiral pool.

  DOI：

  10.1016/s0957-4166(00)86273-4

文献信息

• Synthesis of the oxindole alkaloid (−)-horsfiline
  作者：Claudio Pellegrini、Christoph Strässler、Michael Weber、Hans-Jürg Borschberg

  DOI：10.1016/s0957-4166(00)86273-4

  日期：1994.10

  A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-beta-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the unnatural optical antipode (+)-1, starting from 5-hydroxy-1-tryptophan as the single source from the chiral pool.