ethyl (+/-)-4-(tert-butyldimethylsiloxy)cyclopent-1-enyl(butyl)phosphinate | 872471-57-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl (+/-)-4-(tert-butyldimethylsiloxy)cyclopent-1-enyl(butyl)phosphinate
• 英文别名: (+/-)-ethyl(4-tert-butyldimethylsiloxycyclopent-1-enyl)butylphosphinate
• CAS: 872471-57-3
• 化学式: C₁₇H₃₅O₃PSi
• 分子量: 346.522
• InChiKey: NYVIXPIFSCZUKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (+/-)-4-(tert-butyldimethylsiloxy)cyclopent-1-enyl(butyl)phosphinate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到ethyl (+/-)-4-hydroxy-1-cyclopent-1-enyl(butyl)phosphinate
  参考文献：
  名称：

  Novel γ-Aminobutyric Acid ρ₁Receptor Antagonists; Synthesis, Pharmacological Activity and Structure−Activity Relationships

  摘要：

  gamma-Aminobutyric acid (GABA) analogues based on 4-amino-cyclopent-1-enyl phosphinic acid (34-42) and 3-aminocyclobutane phosphinic acids (51, 52, 56, 57) were investigated in order to obtain selective homomeric rho(1) GABA(C) receptor antagonists. The effect of the stereochemistry and phosphinic acid substituent of these compounds on potency and selectivity within the GABA receptor subtypes was investigated. Compounds of high potency at GABA(C) rho(1) receptors (36, K-B = 0.78 mu M) and selectivity greater than 100 times (41, K-B = 4.97 mu M) were obtained. The data obtained was analyzed along with the known set of GABA(C) rho(1) receptor-ligands, leading to the development of a pharmacophore model for this receptor, which can be used for in silico screening.

  DOI：

  10.1021/jm7015842
• 作为产物：
  描述：

  (+/-)-4-tert-butyldimethylsiloxy-1-cyclopenten-1-yl-trifluoromethanesulfonate 、 ethyl butylphosphinate 在 三乙烯二胺 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 42.0h， 以94%的产率得到ethyl (+/-)-4-(tert-butyldimethylsiloxy)cyclopent-1-enyl(butyl)phosphinate
  参考文献：
  名称：

  Novel γ-Aminobutyric Acid ρ₁Receptor Antagonists; Synthesis, Pharmacological Activity and Structure−Activity Relationships

  摘要：

  gamma-Aminobutyric acid (GABA) analogues based on 4-amino-cyclopent-1-enyl phosphinic acid (34-42) and 3-aminocyclobutane phosphinic acids (51, 52, 56, 57) were investigated in order to obtain selective homomeric rho(1) GABA(C) receptor antagonists. The effect of the stereochemistry and phosphinic acid substituent of these compounds on potency and selectivity within the GABA receptor subtypes was investigated. Compounds of high potency at GABA(C) rho(1) receptors (36, K-B = 0.78 mu M) and selectivity greater than 100 times (41, K-B = 4.97 mu M) were obtained. The data obtained was analyzed along with the known set of GABA(C) rho(1) receptor-ligands, leading to the development of a pharmacophore model for this receptor, which can be used for in silico screening.

  DOI：

  10.1021/jm7015842