(3S)-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline | 159979-11-0

• 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)-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline
• CAS: 159979-11-0
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: JQBAMCZOPMMNBW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.35
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-carbomethoxy-6-methoxy-1,2,3,4-tetrahydro-β-carboline 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.33h， 生成 (2'S,3S)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylic acid
  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-methoxy-1,2,3,4-tetrahydro-β-carboline 在 三甲基氯硅烷 、 对甲苯甲醚 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以93%的产率得到(3S)-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