methyl (2'S,3R)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylate | 159979-09-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2'S,3R)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylate
• CAS: 159979-09-6
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: LXHNBPDZWFAWIU-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2'S,3R)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以98%的产率得到
  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：

  (3'R,5'S)-5-Methoxy-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl (2'S,3R)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-2'-carboxylate
  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.