(2S,3S,3'S)-ethyl-2-benzyl-2',3',4',9'-tetrahydrospiro[oxetane-3,1'-pyrido[3,4-b]indole]-3'-carboxylate

• 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: (2S,3S,3'S)-ethyl-2-benzyl-2',3',4',9'-tetrahydrospiro[oxetane-3,1'-pyrido[3,4-b]indole]-3'-carboxylate
• 英文别名: ethyl (1S,2'S,3S)-2'-benzylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,3'-oxetane]-3-carboxylate
• 化学式: C₂₃H₂₄N₂O₃
• 分子量: 376.455
• InChiKey: QCYJGKPXUMZNQP-JTAQYXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-benzyloxetan-3-one 、 D-色氨酸乙酯盐酸盐 在 碘 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以67%的产率得到(2S,3S,3'S)-ethyl-2-benzyl-2',3',4',9'-tetrahydrospiro[oxetane-3,1'-pyrido[3,4-b]indole]-3'-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones

  摘要：

  2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% cc) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, ally!, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/allcylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.

  DOI：

  10.1021/jo4020485

文献信息

• Asymmetric Synthesis of 2-Substituted Oxetan-3-ones via Metalated SAMP/RAMP Hydrazones
  作者：Joanna V. Geden、Benjamin O. Beasley、Guy J. Clarkson、Michael Shipman

  DOI：10.1021/jo4020485

  日期：2013.12.6

  2-Substituted oxetan-3-ones can be prepared in good yields and enantioselectivities (up to 84% cc) by the metalation of the SAMP/RAMP hydrazones of oxetan-3-one, followed by reaction with a range of electrophiles that include alkyl, ally!, and benzyl halides. Additionally, both chiral 2,2- and 2,4-disubstituted oxetan-3-ones can be made in high ee (86-90%) by repetition of this lithiation/allcylation sequence under appropriately controlled conditions. Hydrolysis of the resultant hydrazones with aqueous oxalic acid provides the 2-substituted oxetan-3-ones without detectable racemization.