2-(4-benzyloxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide | 5884-31-1

• 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: 2-(4-benzyloxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• 英文别名: 2-(4-(benzyloxy)phenyl)-N-(3,4-dimethoxyphenethyl)acetamide；(4-benzyloxy-phenyl)-acetic acid-(3,4-dimethoxy-phenethylamide)；(4-Benzyloxy-phenyl)-essigsaeure-(3,4-dimethoxy-phenaethylamid)；N-(3,4-Dimethoxy-phenaethyl)-2-(4-benzyloxy-phenyl)-acetamid；N-(3,4-Dimethoxy-phenaethyl)-2-(p-benzyloxy-phenyl)-acetamid；N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-phenylmethoxyphenyl)acetamide
• CAS: 5884-31-1
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: BRPKXQPBBSTDCG-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  623.4±55.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 丁酮 为溶剂， 反应 66.0h， 生成 tert-butyl 1-(4-((7-bromoheptyl)oxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzylisoquinoline derivatives as multifunctional agents against Alzheimer’s disease

  摘要：

  A novel series of benzylisoquinoline derivatives were designed, synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). The screening results showed that most of the compounds significantly inhibited cholinesterases (ChEs), human cholinesterases (h-ChEs) and self-induced beta-amyloid (A beta) aggregation. In particular, compound 9k showed the strongest acetylcholinesterase (AChE) inhibitory activity, being 1000-fold and 3-fold more potent than its precursor benzylisoquinoline (10) and the positive control galanthamine, respectively. In addition, 9k was a moderately potent inhibitor for h-ChEs. Compared with precursor benzylisoquinoline (36.0% at 20 mu M), 9k (78.4% at 20 mu M) could further inhibit Ab aggregation. Moreover, 9k showed low cell toxicity in human SH-SY5Y neuroblastoma cells. Therefore, compound 9k might be a promising lead compound for AD treatment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.058
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(4-benzyloxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of benzylisoquinoline derivatives as multifunctional agents against Alzheimer’s disease

  摘要：

  A novel series of benzylisoquinoline derivatives were designed, synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). The screening results showed that most of the compounds significantly inhibited cholinesterases (ChEs), human cholinesterases (h-ChEs) and self-induced beta-amyloid (A beta) aggregation. In particular, compound 9k showed the strongest acetylcholinesterase (AChE) inhibitory activity, being 1000-fold and 3-fold more potent than its precursor benzylisoquinoline (10) and the positive control galanthamine, respectively. In addition, 9k was a moderately potent inhibitor for h-ChEs. Compared with precursor benzylisoquinoline (36.0% at 20 mu M), 9k (78.4% at 20 mu M) could further inhibit Ab aggregation. Moreover, 9k showed low cell toxicity in human SH-SY5Y neuroblastoma cells. Therefore, compound 9k might be a promising lead compound for AD treatment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.058

文献信息

• Application of differential reactivity towards synthesis of lamellarin and 8-oxoprotoberberine derivatives: Study of photochemical properties of aryl-substituted benzofuran-8-oxoprotoberberines
  作者：Sameer Vyasamudri、Ding-Yah Yang

  DOI：10.1016/j.tet.2018.01.042

  日期：2018.3

  A unique differential reactivity between dihydroisoquinolines and 3-nitrocoumarins was observed and was exploited for the efficient construction of lamellarins and their isomeric benzofuran-8-oxoprotoberberine derivatives under acid-catalyzed or base-promoted conditions. Further, these prepared aryl-substituted benzofuran-8-oxoprotoberberine derivatives bearing electron-donating substituents on benzofuran

  观察到二氢异喹啉和3-硝基香豆素之间的独特的差异反应性，并被用于在酸催化或碱促进的条件下有效构建薄片蛋白及其异构体苯并呋喃-8-氧代小ber碱衍生物。此外，发现这些制备的在苯并呋喃部分上带有给电子取代基的芳基取代的苯并呋喃-8-氧代小ber碱衍生物是台式稳定的，但对光敏感，当暴露于可见光下时可发生氧化性开环反应，得到相应的酮产物。在有氧条件下发光。
• Total Synthesis of New 8-(Arylmethyl)berbines
  作者：Maria Valpuesta、Manuela Ariza、Amelia Diaz、Gregorio Torres、Rafael Suau

  DOI：10.1002/ejoc.200901081

  日期：2010.2

  The total synthesis of the natural compound (8S * ,14S * )-8-(4'-hydroxybenzyl)-2,3-dimethoxyberbin-10-ol and its C-8 epimer has been conveniently developed by making use of the diastereoselective Stevens rearrangement of the corresponding N-(arylmethyl)berbinium salts as the key step.

  天然化合物(8S * ,14S * )-8-(4'-羟基苄基)-2,3-二甲氧基berbin-10-ol及其C-8差向异构体的全合成已利用非对映选择性Stevens方便地开发相应的 N-（芳甲基）铽盐的重排是关键步骤。
• Tomita; Yamaguchi, Pharmaceutical Bulletin, 1953, vol. 1, p. 10,12
  作者：Tomita、Yamaguchi

  DOI：——

  日期：——
• Gorbatschewa et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3367,3369;engl.Ausg.S.3404
  作者：Gorbatschewa et al.

  DOI：——

  日期：——
• Baxendale, Ian R.; Davidson, Thomas D.; Ley, Steven V., Heterocycles, 2003, vol. 60, # 12, p. 2707 - 2715
  作者：Baxendale, Ian R.、Davidson, Thomas D.、Ley, Steven V.、Perni, Remedios H.

  DOI：——

  日期：——