ethyl (1-ethoxycarbonyl-1-cyclopentyl)acetate | 108160-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1-ethoxycarbonyl-1-cyclopentyl)acetate
• 英文别名: (1-ethoxycarbonyl-cyclopentyl)-acetic acid ethyl ester；Cyclopentan-carbonsaeure-(1)-essigsaeure-(1)-diaethylester；(1-Aethoxycarbonyl-cyclopentyl)-essigsaeure-aethylester；Ethyl (1-ethoxycarbonyl-1-cyclopentyl)-acetate；Ethyl 1-(2-ethoxy-2-oxoethyl)cyclopentane-1-carboxylate
• CAS: 108160-67-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: UAYGRPWZABQZAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1-ethoxycarbonyl-1-cyclopentyl)acetate 、 2-(4-(2,5-dichlorophenyl)-1-piperazinyl)ethylamine 以15%的产率得到2-{2-[4-(2,5-Dichlorophenyl)-1-piperazinyl]-ethyl}-2-azaspiro[4.4]nonane-1,3-dione
  参考文献：
  名称：

  Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor

  摘要：

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.

  DOI：

  10.1021/jm030944+
• 作为产物：
  描述：

  diethyl 2-bromo-2-(4-bromobutyl)butanedioate 以53%的产率得到ethyl (1-ethoxycarbonyl-1-cyclopentyl)acetate
  参考文献：
  名称：

  1,5-二溴戊烷衍生物电化学还原合成环戊烷衍生物

  摘要：

  将1,3-二溴丙烷或其衍生物与缺电子烯烃通过CuBr催化光化学反应制备的1,5-二溴戊烷衍生物在THF或DMSO溶液中进行电化学还原，得到环戊烷衍生物。

  DOI：

  10.1246/cl.1986.2125

文献信息

• CYCLIC AMIDES AND IMIDES HAVING SELECTIVE ANTAGONIST ACTIVITY AT ALPHA-1D ADRENERGIC RECEPTOR
  申请人：RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.

  公开号：EP1200406B1

  公开（公告）日：2004-11-24
• Vogel, Journal of the Chemical Society, 1928, p. 2025
  作者：Vogel

  DOI：——

  日期：——
• MITANI MICHIHARU; TAKEUCHI HIROSHI; KOYAMA KIKUHIKO, CHEM. LETT.,(1986) N 12, 2125-2126
  作者：MITANI MICHIHARU、 TAKEUCHI HIROSHI、 KOYAMA KIKUHIKO

  DOI：——

  日期：——
• Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor
  作者：Amedeo Leonardi、Daniela Barlocco、Federica Montesano、Giorgio Cignarella、Gianni Motta、Rodolfo Testa、Elena Poggesi、Michele Seeber、Pier G. De Benedetti、Francesca Fanelli

  DOI：10.1021/jm030944+

  日期：2004.4.1

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.
• Synthesis of Cyclopentane Derivatives by Electrochemical Reduction of 1,5-Dibromopentane Derivatives
  作者：Michiharu Mitani、Hiroshi Takeuchi、Kikuhiko Koyama

  DOI：10.1246/cl.1986.2125

  日期：1986.12.5

  When 1,5-dibromopentane derivatives, which were prepared by CuBr-catalyzed photochemical reaction of 1,3-dibromopropane or its derivatives with electron-deficient olefins, were subjected to electrochemical reduction in THF or DMSO solution, cyclopentane derivatives were obtained.

  将1,3-二溴丙烷或其衍生物与缺电子烯烃通过CuBr催化光化学反应制备的1,5-二溴戊烷衍生物在THF或DMSO溶液中进行电化学还原，得到环戊烷衍生物。