2-(2,4-dimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one | 1592683-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,4-dimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-(2,4-Dimethoxyphenyl)tetralin-1-one；2-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1592683-71-0
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: PWAMLYOURSVLAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5,6-dihydronaphtho[1,2-b]benzofuran-9-ol
  参考文献：
  名称：

  5-Carba-pterocarpens: A new scaffold with anti-HCV activity

  摘要：

  The synthesis of a series of 5-carba-pterocarpens derivatives involving the cyclization of alpha-aryl-alpha-tetralones is described. Several compounds demonstrated potent activity and selectivity in vitro against HCV replicon reporter cells. The best profile in Huh7/Rep-Feolb replicon reporter cells was observed with 2h (EC50 = 5.5 mu M/SI = 20), while 2e was the most active in Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (EC50 = 1.5 mu M/SI = 70). Hydroxy groups at A- and D-rings are essential for anti-HCV activity, and substitutions in the A-ring at positions 3 and 4 resulted in enhanced activity of the compounds. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.02.010
• 作为产物：
  描述：

  2,4-二甲氧基溴苯 、 3,4-二氢-1(2H)-萘酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydroxide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以39%的产率得到2-(2,4-dimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  RuPHOX-Ru通过动态动力学拆分催化α-取代四氢萘酮的不对称氢化

  摘要：

  通过动态动力学拆分实现了高效的 RuPHOX-Ru 催化的 α-取代四氢萘酮的不对称氢化，用于合成手性四氢萘酚。机理研究表明，H 2气体加氢，而不是以EtOH溶剂作为氢源的转移加氢，在反应途径中占主导地位。

  DOI：

  10.1039/d2cc01193j

文献信息

• Synthesis and biological evaluation of α-aryl-α-tetralone derivatives as hepatitis C virus inhibitors
  作者：Dinesh Manvar、Talita de A. Fernandes、Jorge L.O. Domingos、Erdenechimeg Baljinnyam、Amartya Basu、Eurides F.T. Junior、Paulo R.R. Costa、Neerja Kaushik-Basu

  DOI：10.1016/j.ejmech.2015.01.057

  日期：2015.3

  The synthesis of a novel series of 1-carba-isoflavanones through the α-arylation of α-tetralones is described. Several of these compounds demonstrated potent activity and selectivity in-vitro against HCV replicon reporter cells. Compound 10 (LQB-314) exhibited the best profile being active and selective in both replicon reporter cells (IC50 1.8 μM, SI > 111 and IC50 4.3 μM, SI > 46 in Huh7/Rep-Feo1b

  描述了通过α-四氢萘酮的α-芳基化合成一系列新的1-carba-异黄烷酮。这些化合物中的几种表现出对HCV复制子报道细胞的有效活性和体外选择性。化合物10（LQB- 314）在两个复制子报告子细胞中均表现出最佳的活性和选择性（IC 50 1.8μM，SI> 111和IC 50 4.3μM，SI> 46在Huh7 / Rep-Feo1b和Huh7.5-FGR中-JC1-Rluc2A）。化合物3（LQB-307）对Huh7.5-FGR-JC1-Rluc2A复制子报告基因细胞更具效力和选择性（IC 50 1.5μM ，SI> 101.4）。
• Synthesis of 5-Carbapterocarpens by α-Arylation of Tetralones Followed by One-Pot Demethylation/Cyclization with BBr₃
  作者：Talita de A. Fernandes、Jorge L. O. Domingos、Luiza I. A. da Rocha、Sabrina de Medeiros、Carmen Nájera、Paulo R. R. Costa

  DOI：10.1002/ejoc.201301505

  日期：2014.2

  Financial support from the Brazilian agencies Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES-DGU Project number 200/09), Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq), Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) is gratefully acknowledged. The Spanish Ministerio de Ciencia e Innovacion (MICINN) (project numbers PHB2008-0037-PC, CTQ2007-62771/BQU

  来自巴西机构 Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior（CAPES-DGU 项目编号 200/09）、Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)、Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) 的财政支持感激地承认。西班牙国家科学与创新部长 (MICINN)（项目编号 PHB2008-0037-PC、CTQ2007-62771/BQU、CTQ2010-20387、Consolider INGENIO 2010 授权编号 CSD2007-00006），（项目编号 CSD2007-00006），(PROMETENEO/Generalita2
• 5-Carba-pterocarpens: A new scaffold with anti-HCV activity
  作者：Talita de A. Fernandes、Dinesh Manvar、Jorge L.O. Domingos、Amartya Basu、Daniel Brian Nichols、Neerja Kaushik-Basu、Paulo R.R. Costa

  DOI：10.1016/j.ejmech.2016.02.010

  日期：2016.4

  The synthesis of a series of 5-carba-pterocarpens derivatives involving the cyclization of alpha-aryl-alpha-tetralones is described. Several compounds demonstrated potent activity and selectivity in vitro against HCV replicon reporter cells. The best profile in Huh7/Rep-Feolb replicon reporter cells was observed with 2h (EC50 = 5.5 mu M/SI = 20), while 2e was the most active in Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (EC50 = 1.5 mu M/SI = 70). Hydroxy groups at A- and D-rings are essential for anti-HCV activity, and substitutions in the A-ring at positions 3 and 4 resulted in enhanced activity of the compounds. Published by Elsevier Masson SAS.
• RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones <i>via</i> a dynamic kinetic resolution
  作者：Jingjing Li、Jianxun Ye、Jiayu Zhou、Jing Li、Delong Liu、Wanbin Zhang

  DOI：10.1039/d2cc01193j

  日期：——

  The efficient RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution has been achieved for the synthesis of chiral tetrahydronaphthols. The mechanism study indicated that hydrogenation with H2 gas, rather than transfer hydrogenation with EtOH solvent as the hydrogen source, predominates in the reaction pathway.

  通过动态动力学拆分实现了高效的 RuPHOX-Ru 催化的 α-取代四氢萘酮的不对称氢化，用于合成手性四氢萘酚。机理研究表明，H 2气体加氢，而不是以EtOH溶剂作为氢源的转移加氢，在反应途径中占主导地位。