1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline | 95427-40-0

• 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-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline
• 英文别名: 1-(3-Hydroxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-isochinolin；2-Methoxy-5-[(6-methoxy-3,4-dihydroisoquinolin-1-yl)methyl]phenol
• CAS: 95427-40-0
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: HBWVFVRHQGVHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline 在 吡啶 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (Z)-2-Formyl-1-<(3-hydroxy-4-methoxyphenyl)methylene>-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

  摘要：

  In the presence of a small amount of RuX(2)[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4-tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100 %) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used fbr synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.

  DOI：

  10.1021/jo00081a007
• 作为产物：
  描述：

  N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以0.427 g的产率得到1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Meuzelaar, Gerrit J.; Van Vliet, Michiel C. A.; Maat, Leendert, European Journal of Organic Chemistry, 1999, # 9, p. 2315 - 2321

  摘要：

  DOI：

文献信息

• Substituted Berbines and Processes for their Synthesis
  申请人：Wang Peter X.

  公开号：US20100056789A1

  公开（公告）日：2010-03-04

  The present invention provides processes for the synthesis of substituted berbine compounds. Also provided are intermediates used in the synthesis of substituted berbine compounds.

  本发明提供了合成取代苯并喹啉化合物的方法。还提供了在合成取代苯并喹啉化合物中使用的中间体。
• One-Pot Preparation of Hexahydroisoquinolines from Dihydroisoquinolines
  申请人：Grote Christopher W.

  公开号：US20110071300A1

  公开（公告）日：2011-03-24

  The present invention provides an efficient process for the preparation of hexahydroisoquinolines from dihydroisoquinolines. In particular, the invention provides a good yielding, one-pot process for the synthesis of hexahydroisoquinolines.

  本发明提供了一种从二氢异喹啉制备六氢异喹啉的高效过程。特别地，本发明提供了一种产率高、一锅法合成六氢异喹啉的方法。
• Process for the Preparation of Hexahydroisoquinolines from 1,2,3,4-Tetrahydroisoquinolines
  申请人：Cantrell Gary L.

  公开号：US20090247756A1

  公开（公告）日：2009-10-01

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process for the asymmetric reduction of an imine moiety in a 3,4-dihydroisoquinoline to produce a tetrahydroisoquinoline, followed by a Birch reduction to produce a hexahydroisoquinoline. In various embodiments, the 3,4-dihydroisoquinoline contains a phenol moiety protected with a labile protecting group. In other embodiments, the imine reduction reaction mixture contains silver tetrafluoroborate.

  本发明涉及吗啡内酯的合成过程。特别是一种过程，用于不对称还原3,4-二氢异喹啉中的亚胺官能团，以产生四氢异喹啉，然后进行Birch还原以产生六氢异喹啉。在各种实施例中，3,4-二氢异喹啉含有一个带有不稳定保护基的酚官能团。在其他实施例中，亚胺还原反应混合物含有四氟硼酸银。
• Preparation of Hexahydroisoquinolines from Dihydroisoquinolines
  申请人：Cantrell Gary L.

  公开号：US20100022776A1

  公开（公告）日：2010-01-28

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process for the asymmetric reduction of an imine moiety in a 3,4-dihydroisoquinoline to produce a tetrahydroisoquinoline, followed by a Birch reduction to produce a hexahydroisoquinoline. In various embodiments, the 3,4-dihydroisoquinoline contains a phenol moiety protected with a labile protecting group. In other embodiments, the imine reduction reaction mixture contains silver tetrafluoroborate.

  本发明涉及吗啡型物质的合成过程。特别是，本发明提供了一种过程，用于不对称还原3,4-二氢异喹啉中的亚胺官能团，以产生四氢异喹啉，然后进行Birch还原以产生六氢异喹啉。在各种实施例中，3,4-二氢异喹啉包含一个用不稳定保护基保护的酚官能团。在其他实施例中，亚胺还原反应混合物含有四氟硼酸银。
• A process for the preparation of hexahydroisoquinolines from 1,2,3,4-Tetrahydroisoquinolines
  申请人：Mallinckrodt Inc.

  公开号：EP2149559A1

  公开（公告）日：2010-02-03

  The present invention is directed to processes for the synthesis of morphinans. In particular, a Birch reduction to produce a hexahydroisoquinoline.

  本发明涉及吗啡类化合物的合成工艺。特别是桦木还原法生产六氢异喹啉。