ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylpropionate | 177587-73-4

• 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-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylpropionate
• 英文别名: Ethyl 2-[[4-methoxy-3-(2-phenylethoxy)phenyl]methyl]butanoate
• CAS: 177587-73-4
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: DAWQZSYYEGLVCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylpropionate 在 氢氧化钾 、 叠氮磷酸二苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 25.5h， 生成 1-(4-Methoxy-3-phenethyloxy-benzyl)-propylamine
  参考文献：
  名称：

  Synthesis and SAR of 1-Alkyl-2-phenylethylamine Derivatives Designed from N,N-Dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine To Discover σ₁ Ligands

  摘要：

  The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective ol affinity.

  DOI：

  10.1021/jm990135j
• 作为产物：
  描述：

  2-膦酰丁酸三乙脂 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 2.5h， 生成 ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylpropionate
  参考文献：
  名称：

  Synthesis and SAR of 1-Alkyl-2-phenylethylamine Derivatives Designed from N,N-Dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine To Discover σ₁ Ligands

  摘要：

  The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective ol affinity.

  DOI：

  10.1021/jm990135j

文献信息

• OPTICALLY ACTIVE SUBSTITUTED PHENYLALKYLAMINE DERIVATIVES
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0870758A1

  公开（公告）日：1998-10-14

  The present invention relates to an optically active, substituted phenylalkylamine derivative represented by Formula [1]:    wherein A is a substituted or non-substituted phenyl or thienyl; X1 is hydrogen, halogen, hydroxyl or a substituted or non-substituted C1-5 alkoxy; R1 and R2 are equally or differently hydrogen, C1-7 alkyl, C3-7 alkenyl or C3-7 alkynyl; R3 is C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl; n is an integer from 2 to 5; and m is an integer from 1 to 4, or a pharmaceutically acceptable salt thereof, and pharmaceutical use of such compound or salt. The compound of the invention is excellent in sigma 1 receptor antagonism and useful for treating schizophrenia, depression, anxiety, cerebrovascular diseases/senile troublesome behaviors, and cognitive dysfunctions and motor dysfunctions such as Alzheimer's disease, Parkinson's disease and Huntington's disease which are neurodegenerative diseases. Further, the compound of the invention is also useful for treating dependence resulted from drug abuse.

  本发明涉及一种由式[1]表示的具有光学活性的取代苯基烷基胺衍生物： 其中 A 是取代或非取代的苯基或噻吩基；X1 是氢、卤素、羟基或取代或非取代的 C1-5 烷氧基；R1 和 R2 相同或不同地是氢、C1-7 烷基、C3-7 烯基或 C3-7 烷炔基；R3 是 C1-10 烷基、C2-10 烯基或 C2-10 烷炔基；n 是 2 至 5 的整数；m 是 1 至 4 的整数、 或其药学上可接受的盐，以及这种化合物或盐的药物用途。本发明化合物具有优异的σ1受体拮抗作用，可用于治疗精神分裂症、抑郁症、焦虑症、脑血管疾病/躁狂症、认知功能障碍和运动功能障碍，如阿尔茨海默病、帕金森病和亨廷顿病等神经退行性疾病。此外，本发明的化合物还可用于治疗药物滥用导致的依赖性。
• US5990151A
  申请人：——

  公开号：US5990151A

  公开（公告）日：1999-11-23
• Synthesis and SAR of 1-Alkyl-2-phenylethylamine Derivatives Designed from <i>N</i>,<i>N</i>-Dipropyl-4-methoxy-3-(2-phenylethoxy)phenylethylamine To Discover σ₁ Ligands
  作者：Atsuro Nakazato、Toshihito Kumagai、Kohmei Ohta、Shigeyuki Chaki、Shigeru Okuyama、Kazuyuki Tomisawa

  DOI：10.1021/jm990135j

  日期：1999.9.1

  The synthesis and structure-activity relationships (SAR) of 1-alkyl-2-phenylethylamine derivatives 5-8 designed from N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine hydrochloride (1, NE-100) are presented. The SAR between compound 1 and 1-alkyl-2-phenylethylamine derivatives suggested that the alkyl group on the 1-position carbon of 2-[4-methoxy-3-(2-phenylethyl)phenyl]ethylamine derivatives played the role of one of the propyl groups on the aminic nitrogen of compound 1. (-)-N-Propyl-1-butyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6d, NE-537) and (-)-N-propyl-1-(3-methybutyl)2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride ((-)-6i, NE-535), typical compounds in this series, have potent and selective ol affinity.