Ethyl 3-[2-(4-methoxyphenyl)ethylamino]-3-oxopropanoate | 200216-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Ethyl 3-[2-(4-methoxyphenyl)ethylamino]-3-oxopropanoate
• CAS: 200216-57-5
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: XCEJKTTVEVMROS-UHFFFAOYSA-N

物化性质

• 沸点：
  459.6±35.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[2-(4-methoxyphenyl)ethylamino]-3-oxopropanoate 在 platinum(IV) oxide lithium aluminium tetrahydride 、 polyphosphate ester 、 氢气 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 t-butyl 7-dimethylcarbamoyloxy-1-(2-hydroxyethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  A conformational restriction approach to the development of dual inhibitors of acetylcholinesterase and serotonin transporter as potential agents for Alzheimer's disease

  摘要：

  Alzheimer's disease (AD) has been treated with acetylcholinesterase (AChE) inhibitors such as donepezil. However, the clinical usefulness of AChE inhibitors is limited mainly due to their adverse peripheral effects. Depression seen in AD patients has been treated with serotonin transporter (SERT) inhibitors. We considered that combining SERT and AChE inhibition could improve the clinical usefulness of AChE inhibitors. In a previous paper, we found a potential dual inhibitor, 1, of AChE (IC50 = 101 nM) and SERT (IC50 = 42 nM), but its AChE inhibition activity was less than donepezil (IC50 = 10 nM). Here, we report the conformationally restricted (R)-18a considerably enhanced inhibitory activity against AChE (IC50 14 nM) and SERT (IC50 = 6 nM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00452-8
• 作为产物：
  描述：

  2-(4-甲氧苯基)乙胺 、 氯甲酰乙酸乙酯 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 以58%的产率得到Ethyl 3-[2-(4-methoxyphenyl)ethylamino]-3-oxopropanoate
  参考文献：
  名称：

  Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders

  摘要：

  The aza-annulation of enamino ester substrates has been demonstrated as an efficient alternative to the syntheses of non-benzodiazepine sleep inducers. Enamino ester substrates derived from aryl, thiophene, and indole functionality were prepared from the corresponding ethyl amines by isothiocyanate formation followed by acid catalyzed cyclization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10297-0

文献信息

• [EN] 3-SUBSTITUTED PYRROLO (2.1-A) ISOQUINOLINE DERIVATIVES<br/>[FR] DERIVES DE LA PYRROLO (2.1-A) ISOQUINOLEINE SUBSTITUES EN 3
  申请人：BAYER AG

  公开号：WO2003014115A1

  公开（公告）日：2003-02-20

  The present invention relates to pyrrolo[2.1-a]dihydroisoquinolines which are inhibitors of phosphodiesterase 10a and can be used for combating cancer.
• [EN] 3-SUBSTITUTED PYRROLO[2.1-A]ISOQUINOLINE DERIVATIVES<br/>[FR] DERIVES DE 3-PYRROLO[2.1-A]ISOQUINOLEINE SUBSTITUES
  申请人：BAYER AG

  公开号：WO2003014117A1

  公开（公告）日：2003-02-20

  The present invention relates to 3-substituted pyrrolo[2.1-a]dihydroisoquinolines which are in-hibitors of phosphodiesterase 10a and can be used for combating cancer.