2-(benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one | 749799-40-4

• 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-(benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2-[(benzyl-methyl-amino)-methyl]-3,4-dihydro-2H-naphthalen-1-one；(+/-)-1-Oxo-2-[(methyl-benzyl-amino)-methyl]-1.2.3.4-tetrahydro-naphthalin；2-[(Benzyl-methyl-amino)-methyl]-3,4-dihydro-2H-naphthalin-1-on；2-[[benzyl(methyl)amino]methyl]-3,4-dihydro-2H-naphthalen-1-one
• CAS: 749799-40-4
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: YFIIDXSHXVCMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 生成 cis-benzyl-methyl-[1-(4-trifluoromethylphenoxy)-1,2,3,4-tetrahydronaphthalen-2-ylmethyl]-amine
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032
• 作为产物：
  描述：

  2-methylene-1-tetralone 、 N-甲基苄胺 在 aluminum oxide 作用下， 以90%的产率得到2-(benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  氧化铝催化的仲胺向环外α，β-不饱和酮的加成反应

  摘要：

  在氧化铝的存在下，已将仲胺迈克尔加成到环外α，β-不饱和酮上，获得了优异的收率。在不存在氧化铝的情况下，经过很长的反应时间后，对于许多副产物，反应不会进行或产率低。

  DOI：

  10.1016/s0040-4039(00)71511-5

文献信息

• DE514418
  申请人：——

  公开号：——

  公开（公告）日：——