(+/-)-1-(m-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisochinolin | 93024-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (+/-)-1-(m-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisochinolin
• 英文别名: 1-benzyl-1,2,3,4,5,6,7,8-octahydro-isoquinoline；1-Benzyl-1,2,3,4,5,6,7,8-octahydro-isochinolin；1-Benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline
• CAS: 93024-45-4
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: QYXMTRMBTVDSOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(m-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisochinolin 、 磷酸 、 水 生成 rac-morphinane
  参考文献：
  名称：

  Grewe et al., Justus Liebigs Annalen der Chemie, 1949, vol. 564, p. 161,192

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-环己烯基)乙胺 在 盐酸 、 苯 作用下， 生成 (+/-)-1-(m-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisochinolin
  参考文献：
  名称：

  Grewe et al., Justus Liebigs Annalen der Chemie, 1953, vol. 581, p. 85,107

  摘要：

  DOI：

文献信息

• Method for preparing (S)-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline compound
  申请人：FUDAN UNIVERSITY

  公开号：US11345941B2

  公开（公告）日：2022-05-31

  This application relates to biological pharmacy and biochemical engineering, and more particularly to a method of preparing a (S)-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline compound. This method includes: subjecting a 1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline raceme as a substrate to selective oxidation in the presence of a monoamine oxidase and the non-selective reduction to prepare the (S)-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline compound, where the monoamine oxidase has an amino acid sequence as shown in SEQ ID NO: 1 or an amino acid sequence having an identity of more than 80% with SEQ ID NO: 1. The kinetic resolution is carried out in the presence of the monoamine oxidase as a catalyst and a reductant, and the resulting product has a high chiral purity.

  本申请涉及生物药剂学和生物化学工程，更具体地说，涉及一种制备(S)-1-苄基-1,2,3,4,5,6,7,8-八氢异喹啉化合物的方法。该方法包括：将作为底物的 1-苄基-1,2,3,4,5,6,7,8-八氢异喹啉外消旋体在单胺氧化酶存在下进行选择性氧化和非选择性还原，以制备(S)-1-苄基-1,2,3,4,5,6,7,8-八氢异喹啉化合物，其中单胺氧化酶具有如 SEQ ID NO：1 所示的氨基酸序列或与 SEQ ID NO: 1 相同度大于 80% 的氨基酸序列。动力学解析是在单胺氧化酶作为催化剂和还原剂存在的情况下进行的，得到的产物具有很高的手性纯度。
• Henecka, Justus Liebigs Annalen der Chemie, 1953, vol. 583, p. 110,126
  作者：Henecka

  DOI：——

  日期：——
• METHOD FOR PREPARING (S)-1-BENZYL-1,2,3,4,5,6,7,8-OCTAHYDROISOQUINOLINE COMPOUND
  申请人：FUDAN UNIVERSITY

  公开号：US20210087595A1

  公开（公告）日：2021-03-25

  This application relates to biological pharmacy and biochemical engineering, and more particularly to a method of preparing a (S)-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline compound. This method includes: subjecting a 1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline raceme as a substrate to selective oxidation in the presence of a monoamine oxidase and the non-selective reduction to prepare the (S)-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline compound, where the monoamine oxidase has an amino acid sequence as shown in SEQ ID NO: 1 or an amino acid sequence having an identity of more than 80% with SEQ ID NO: 1. The kinetic resolution is carried out in the presence of the monoamine oxidase as a catalyst and a reductant, and the resulting product has a high chiral purity.
• Grewe et al., Justus Liebigs Annalen der Chemie, 1949, vol. 564, p. 161,192
  作者：Grewe et al.

  DOI：——

  日期：——
• Grewe et al., Justus Liebigs Annalen der Chemie, 1953, vol. 581, p. 85,107
  作者：Grewe et al.

  DOI：——

  日期：——