(4-benzyloxy-3-methoxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) | 13255-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-benzyloxy-3-methoxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide)
• 英文别名: (4-Benzyloxy-3-methoxy-phenyl)-essigsaeure-(4-benzyloxy-3-methoxy-phenaethylamid)；N-<3-Methoxy-4-benzyloxy-phenaethyl>-2-<4-benzyloxy-3-methoxy-phenyl>-acetamid；N-<3-Methoxy-4-benzyloxyphenethyl>-2-<3-methoxy-4-benzyloxyphenyl>-acetamid；N-(4-Benzyloxy-3-methoxy-phenylethyl)-4-benzyloxy-3-methoxyphenylacetamid；2-[4-(benzyloxy)-3-methoxyphenyl]-N-{2-[4-(benzyloxy)-3-methoxyphenyl]ethyl}acetamide；2-(3-methoxy-4-phenylmethoxyphenyl)-N-[2-(3-methoxy-4-phenylmethoxyphenyl)ethyl]acetamide
• CAS: 13255-23-7
• 化学式: C₃₂H₃₃NO₅
• 分子量: 511.618
• InChiKey: XASSQMNHZJGQPI-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C(Solv: ethanol (64-17-5))
• 沸点：
  712.6±60.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-benzyloxy-3-methoxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) 在 盐酸 、 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 (13aR)-3,11-dimethoxy-2,10-bis(phenylmethoxy)-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
  参考文献：
  名称：

  [EN] TETRAHYDROPROTOBERBINE COMPOUNDS AND USES THEREOF IN THE TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND NEURODEGENERATIVE DISEASES
  [FR] COMPOSÉS TÉTRAHYDROPROTOBERBINES ET LEURS UTILISATIONS DANS LE TRAITEMENT DE MALADIES NEUROLOGIQUES, PSYCHIATRIQUES ET NEURODÉGÉNÉRATIVES

  摘要：

  提供了Tetrahydroprotoberbine (THPB)化合物及其在治疗神经系统、精神疾病和神经退行性疾病中的用途。这些化合物包括d-govadine、l-govadine和racemic govadine，以及通式(I)的d-THPBs。还提供了制备通式(I)化合物和d-、l-govadine的对映选择性过程。(I)

  公开号：

  WO2013020229A1
• 作为产物：
  描述：

  4-(2-氨基乙基)-2-甲氧基苯酚 在 sodium ethanolate 作用下， 生成 (4-benzyloxy-3-methoxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide)
  参考文献：
  名称：

  Die Synthese von 1-Benzylisochinolinen mit Guajacyl-Gruppierung

  摘要：

  DOI：

  10.1007/bf00913844

文献信息

• First enantioselective syntheses of the dopamine D1 and D2 receptor modulators, (+)- and (−)-govadine
  作者：Huimin Zhai、James Miller、Glenn Sammis

  DOI：10.1016/j.bmcl.2012.01.005

  日期：2012.2

  There is a pressing need to find and develop new antipsychotic agents for the treatment of schizophrenia. Current drugs primarily target dopamine D2receptors and are only effective in the treatment of the positive symptoms of this indication. The tetrahydroprotoberberine natural product (+/-)- govadine has shown unique promise for the treatment of both the positive and negative symptoms of schizophrenia as it targets both dopamine D1 and D2 receptors. However, further clinical research has been hindered by the lack of availability of significant quantities of enantioenriched material. A new, enantioselective synthetic route has been developed that affords (-)- govadine in 39% overall yield over 5-steps from commercially available dopamine and homovanillic acid derivatives. Using only minor modifications in the synthetic route, (+)-govadine can be synthesized in comparable yields and enantioselectivities. The route is readily scalable as every intermediate was purified by crystallization and no flash column chromatography was necessary. (C) 2012 Published by Elsevier Ltd.
• TETRAHYDROPROTOBERBINE COMPOUNDS AND USES THEREOF IN THE TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND NEURODEGENERATIVE DISEASES
  申请人：Miller James Jackson

  公开号：US20170100389A1

  公开（公告）日：2017-04-13

  Tetrahydroprotoberbine (THPB) compounds and their use in the treatment of neurological, psychiatric and neurodegenerative diseases is provided. The compounds include d-govadine, l-govadine and racemic govadine, as well as d-THPBs of general formula (I). Enantioselective processes for preparing compounds of formula (I), and d- and l-govadine are also provided.
• [EN] TETRAHYDROPROTOBERBINE COMPOUNDS AND USES THEREOF IN THE TREATMENT OF NEUROLOGICAL, PSYCHIATRIC AND NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSÉS TÉTRAHYDROPROTOBERBINES ET LEURS UTILISATIONS DANS LE TRAITEMENT DE MALADIES NEUROLOGIQUES, PSYCHIATRIQUES ET NEURODÉGÉNÉRATIVES
  申请人：MILLER JAMES JACKSON

  公开号：WO2013020229A1

  公开（公告）日：2013-02-14

  Tetrahydroprotoberbine (THPB) compounds and their use in the treatment of neurological, psychiatric and neurodegenerative diseases is provided. The compounds include d-govadine, l-govadine and racemic govadine, as well as d-THPBs of general formula (I). Enantioselective processes for preparing compounds of formula (I), and d- and l-govadine are also provided.(I)

  提供了Tetrahydroprotoberbine (THPB)化合物及其在治疗神经系统、精神疾病和神经退行性疾病中的用途。这些化合物包括d-govadine、l-govadine和racemic govadine，以及通式(I)的d-THPBs。还提供了制备通式(I)化合物和d-、l-govadine的对映选择性过程。(I)
• Die Synthese von 1-Benzylisochinolinen mit Guajacyl-Gruppierung
  作者：K. Kratzl、G. Billek

  DOI：10.1007/bf00913844

  日期：——