(R)-1-(2-hydroxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

• 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: (R)-1-(2-hydroxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole
• 英文别名: 2-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]phenol
• 化学式: C₁₇H₁₆N₂O
• mdl: MFCD02612683
• 分子量: 264.327
• InChiKey: DLRFYHZDPBAQHF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)phenol 在 果糖 、 水 作用下， 以 乙醇 为溶剂， 以48%的产率得到(R)-1-(2-hydroxyphenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus

  摘要：

  beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C-1-C-11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C-15 and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.036

文献信息

• Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
  作者：Marlene Espinoza-Moraga、Tania Petta、Marco Vasquez-Vasquez、V. Felipe Laurie、Luis A.B. Moraes、Leonardo Silva Santos

  DOI：10.1016/j.tetasy.2010.06.036

  日期：2010.8

  beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C-1-C-11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C-15 and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.