(R)-1-(2-aminophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-1-(2-aminophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]aniline
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: JNIAUZSUTVRQIF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-1-(2-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 氨 、 铜 、 copper(l) chloride 作用下， 70.0 ℃ 、4.5 MPa 条件下， 反应 120.0h， 以82%的产率得到(S)-1-(2-aminophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Substituted Isoquinolines by Noyori Transfer Hydrogenation:  Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit

  摘要：

  Transfer hydrogenation using the Noyori catalyst 5-Ts is effective for the enantioselective hydrogenation of imines containing fully substituted nitrogen groups (12 or 13). Analogues such as Ile could not be reduced in practical yield, apparently due to product inhibition of the catalyst. Asymmetric transfer hydrogenation of the aniline imine 8a was possible, but required. impractical purity levels for the substrate, and the nitro analogue 7 could not be reduced efficiently. The best results were Obtained with the bromophenyl imine 20, In the case of 20b, the product 21b was formed with 98.7% ee, and the material could be upgraded to >99% ee by crystallization of the hydrochloride salt. Reaction of 21b with NH3 or MeNH2 in the presence of Cu/CuCl gave the chiral anilines 10b or 23b. The latter substance is comparable to the commercially available 1 as a chiral proton donor fog amide enolates and provides access to the hitherto unavailable enantiomeric series.

  DOI：

  10.1021/jo990594s