2-(2-bromobenzyl)-6-methoxy-tetralone | 1253049-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(2-bromobenzyl)-6-methoxy-tetralone
• 英文别名: 2-[(2-bromophenyl)methyl]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1253049-92-1
• 化学式: C₁₈H₁₇BrO₂
• 分子量: 345.236
• InChiKey: GKGZPFKBDIIBHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-bromobenzyl)-6-methoxy-tetralone 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 C₂₁H₂₇O₃P 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 12.0h， 生成 6-methyl-5,6,7,8-tetrahydro-10H-6,12a-methanodibenzo[a,c][8]annulen-10-one
  参考文献：
  名称：

  钯催化脱芳香化反应构建各种桥联多环骨架。

  摘要：

  开发了功能强大的钯催化脱芳香环化反应，可轻松进入八种带有各种环尺寸和杂环的桥连四环骨架。用这种方法，合成了几种天然产物的骨架或类似物，包括微管蛋白B和龙血烯酮。通过使用手性钯催化剂，不对称脱芳香环化反应使各种对映体富集的桥联多环体系的ee高达99％。

  DOI：

  10.1002/anie.202000953
• 作为产物：
  描述：

  2-(2-bromobenzyl)-6-hydroxy-tetralone 、 碘甲烷 在 potassium carbonate 作用下， 以100%的产率得到2-(2-bromobenzyl)-6-methoxy-tetralone
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones

  摘要：

  A series of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones were prepared, using an efficient synthetic scheme, and evaluated for their inhibitory activity against cytochrome P450C24A1 (CYP24A1) hydroxylase. In general the reduced benzyl tetralones were more active than the parent benzylidene tetralones. The 2-ethyl and 2-trifluoromethyl benzyl tetralone derivatives (4c and 4b) showed optimal activity in this series with IC(50) values of 1 92 mu M and 2.08 mu M, respectively compared with the standard ketoconazole IC(50) 0.52 mu M. The 2-bromobenzyl tetralone (4d) showed a preference for CYP27A1 (IC(50) 59 nM) over CYP24A1 (IC(50) 163 mu M) and may be a useful lead in CYP27A1 inhibition studies The 2-ethylphenyl benzyl derivative (9c), which showed weak activity against the wild type CYP24A1 (IC(50) 25.57 mu M), exhibited enhanced inhibitory activity towards L148F and M416T mutants, this difference in activity for the L148F mutant has been explained using molecular modelling (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.001

文献信息

• Enantioselective α‐Carbonylative Arylation for Facile Construction of Chiral Spirocyclic β,β′‐Diketones
  作者：Ting Wu、Qinghai Zhou、Wenjun Tang

  DOI：10.1002/anie.202101668

  日期：2021.4.26

  We herein describe the first enantioselective α‐carbonylative arylation, providing a diverse set of chiral spiro β,β′‐diketones bearing various ring sizes and functionalities in high yields and good to excellent enantioselectivities. Calculations suggest the transformation proceeds through reductive elimination instead of nucleophilic addition pathway.

  我们在此描述了第一个对映选择性的α-羰基芳基化反应，提供了多种多样的手性螺环β，β'-二酮，具有高收率和良好至优异的对映选择性的各种环大小和功能。计算表明该转化是通过还原消除而不是亲核加成途径进行的。
• Construction of Various Bridged Polycyclic Skeletons by Palladium‐Catalyzed Dearomatization
  作者：Xingye Mu、Hanxiao Yu、Henian Peng、Wenrui Xiong、Ting Wu、Wenjun Tang

  DOI：10.1002/anie.202000953

  日期：2020.5.18

  entry to eight types of bridged tetracyclic skeletons bearing various ring sizes and heterocycles. With this method, several skeletons or analogs of natural products including tubingensin B and dracaenones are synthesized. Asymmetric dearomative cyclization enables various enantiomerically enriched bridged polycyclic systems with up to 99% ee by employing a chiral palladium catalyst.

  开发了功能强大的钯催化脱芳香环化反应，可轻松进入八种带有各种环尺寸和杂环的桥连四环骨架。用这种方法，合成了几种天然产物的骨架或类似物，包括微管蛋白B和龙血烯酮。通过使用手性钯催化剂，不对称脱芳香环化反应使各种对映体富集的桥联多环体系的ee高达99％。
• Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones
  作者：Ahmed S. Aboraia、Bart Makowski、Alba Bahja、David Prosser、Andrea Brancale、Glenville Jones、Claire Simons

  DOI：10.1016/j.ejmech.2010.07.001

  日期：2010.10

  A series of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones were prepared, using an efficient synthetic scheme, and evaluated for their inhibitory activity against cytochrome P450C24A1 (CYP24A1) hydroxylase. In general the reduced benzyl tetralones were more active than the parent benzylidene tetralones. The 2-ethyl and 2-trifluoromethyl benzyl tetralone derivatives (4c and 4b) showed optimal activity in this series with IC(50) values of 1 92 mu M and 2.08 mu M, respectively compared with the standard ketoconazole IC(50) 0.52 mu M. The 2-bromobenzyl tetralone (4d) showed a preference for CYP27A1 (IC(50) 59 nM) over CYP24A1 (IC(50) 163 mu M) and may be a useful lead in CYP27A1 inhibition studies The 2-ethylphenyl benzyl derivative (9c), which showed weak activity against the wild type CYP24A1 (IC(50) 25.57 mu M), exhibited enhanced inhibitory activity towards L148F and M416T mutants, this difference in activity for the L148F mutant has been explained using molecular modelling (C) 2010 Elsevier Masson SAS. All rights reserved.