debromowoodinine | 138690-69-4

• 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: debromowoodinine
• 英文别名: (1R)-2-methyl-1-[(2S)-1-methylpyrrolidin-2-yl]-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 138690-69-4
• 化学式: C₁₇H₂₃N₃
• 分子量: 269.39
• InChiKey: XIBUEMRHGMAPMS-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  22.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  debromowoodinine 在 溴 、 溶剂黄146 作用下， 以10%的产率得到(-) woodinine
  参考文献：
  名称：

  Diastereoselective pictet-spengler reactions of L-(boc)prolinal: a biomimetic synthesis of eudistomins H and I, and woodinine

  摘要：

  The carbon skeleton present in eudistomins H, I and in woodinine may be envisioned to be biosynthetically derived from tryptamine and L-prolinal by a Pictet-Spengler type reaction. The diastereoselectivity (> 5:1) of this reaction, and the elaboration of the Pictet-Spengler products into the title compounds is described. The absolute stereochemistry of (-) woodinine is thereby established.

  DOI：

  10.1016/s0040-4039(00)93484-1
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 lithium aluminium tetrahydride 、 二异丁基氢化铝 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.5h， 生成 debromowoodinine
  参考文献：
  名称：

  Diastereoselective pictet-spengler reactions of L-(boc)prolinal: a biomimetic synthesis of eudistomins H and I, and woodinine

  摘要：

  The carbon skeleton present in eudistomins H, I and in woodinine may be envisioned to be biosynthetically derived from tryptamine and L-prolinal by a Pictet-Spengler type reaction. The diastereoselectivity (> 5:1) of this reaction, and the elaboration of the Pictet-Spengler products into the title compounds is described. The absolute stereochemistry of (-) woodinine is thereby established.

  DOI：

  10.1016/s0040-4039(00)93484-1

文献信息

• Synthesis of the Alkaloid Woodinine.
  作者：Siavosh Mahboobi

  DOI：10.1002/ardp.19923250411

  日期：——

  Synthese des Alkaloids Woodinin

  生物碱木地宁的合成
• X-ray Crystal Structure of Woodinine and Conformational Analysis by Semiempirical and ¹H-NMR Methods
  作者：S. Mahboobi、S. Dove、P. J. Bednarski、S. Kuhr、T. Burgemeister、D. Schollmeyer

  DOI：10.1021/np9700073

  日期：1997.6.1

  The molecular structure of (-)-woodinine (1), a carboline-based alkaloid with antibacterial and antimycobacterial activities, was investigated by X-ray crystallographic, NMR, and semiempirical quantum chemical methods. Compound 1 was prepared by reacting 5-bromotryptamine and (S)-(-)-N-(tert-butoxycarbonyl)pyrrolidine-2-carboxyaldehyde in a Pictet-Spengler-type reaction. The debrominated analogue of 1 was methylated at the indole nitrogen with methyl methane sulfonate after deprotonation with n-BuLi. The X-ray crystal structure of 1 showed the indole ring in the expected planar conformation, the pyrrolidine ring in an envelope conformation, and a weak intramolecular hydrogen bond between the pyrrolidine nitrogen and the proton of the indole nitrogen. NMR experiments indicated that this hydrogen bond is not present in solution and that further differences exist between the crystal and the solution structures of 1. By semiempirical quantum chemical methods, different local energy minimum conformations of 1, resulting from inversions within the piperideine moiety and from rotation of the pyrrolidine ring, were calculated. The totality of all NOE signals can only be explained to originate from a population of some of these conformers, and additionally from different envelope and twisted conformations of the pyrrolidine ring.
• Diastereoselective pictet-spengler reactions of L-(boc)prolinal: a biomimetic synthesis of eudistomins H and I, and woodinine
  作者：James McNulty、Ian W.J Still

  DOI：10.1016/s0040-4039(00)93484-1

  日期：1991.9

  The carbon skeleton present in eudistomins H, I and in woodinine may be envisioned to be biosynthetically derived from tryptamine and L-prolinal by a Pictet-Spengler type reaction. The diastereoselectivity (> 5:1) of this reaction, and the elaboration of the Pictet-Spengler products into the title compounds is described. The absolute stereochemistry of (-) woodinine is thereby established.
• McNulty, James; Still, Ian W. J., Journal of the Chemical Society. Perkin transactions I, 1994, # 10, p. 1329 - 1338
  作者：McNulty, James、Still, Ian W. J.

  DOI：——

  日期：——