4,4-Diethoxy-2-(2-fluoro-phenyl)-butyronitrile | 88897-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-Diethoxy-2-(2-fluoro-phenyl)-butyronitrile
• 英文别名: 4,4-diethoxy-2-(2-fluorophenyl)butanenitrile
• CAS: 88897-66-9
• 化学式: C₁₄H₁₈FNO₂
• 分子量: 251.301
• InChiKey: XYAVNMBTBQGCCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,4-Diethoxy-2-(2-fluoro-phenyl)-butyronitrile 在 吡啶 、 aluminium hydride 、 盐酸 、 戊醇 、 盐酸羟胺 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 (2R,7S,8aS)-2-(2-Fluoro-phenyl)-octahydro-indolizin-7-ylamine
  参考文献：
  名称：

  Substituted benzamides with conformationally restricted side chains. 2. Indolizidine derivatives as central dopamine receptor antagonists

  摘要：

  The substituted benzamides metoclopramide (1) and clebopride (3) are stimulants of gastric motility. They are also central dopamine receptor antagonists with 3 being the more potent. This is presumed to be due to an additional interaction of its N-benzyl group with the receptor. The effect of restricting the conformation of this group by replacing the N-benzylpiperidine side chain of 3 by phenyl-substituted quinolizidines and indolizidines has been investigated. Only the indolizidines had significant activity, the nature of which depended upon the orientation of the phenyl substituent. The 2 alpha-phenyl isomers 5d-h were potent central dopamine D2 receptor antagonists with 5h showing selectivity for the limbic system. The 2 beta-phenyl isomer 5c was a gastric motility stimulant devoid of significant central dopamine receptor antagonist activity. Implications on receptor models are discussed.

  DOI：

  10.1021/jm00117a008
• 作为产物：
  描述：

  2-氟苯基乙腈 、 2-溴-1,1-二乙氧基乙烷 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 4,4-Diethoxy-2-(2-fluoro-phenyl)-butyronitrile
  参考文献：
  名称：

  Substituted benzamides with conformationally restricted side chains. 2. Indolizidine derivatives as central dopamine receptor antagonists

  摘要：

  The substituted benzamides metoclopramide (1) and clebopride (3) are stimulants of gastric motility. They are also central dopamine receptor antagonists with 3 being the more potent. This is presumed to be due to an additional interaction of its N-benzyl group with the receptor. The effect of restricting the conformation of this group by replacing the N-benzylpiperidine side chain of 3 by phenyl-substituted quinolizidines and indolizidines has been investigated. Only the indolizidines had significant activity, the nature of which depended upon the orientation of the phenyl substituent. The 2 alpha-phenyl isomers 5d-h were potent central dopamine D2 receptor antagonists with 5h showing selectivity for the limbic system. The 2 beta-phenyl isomer 5c was a gastric motility stimulant devoid of significant central dopamine receptor antagonist activity. Implications on receptor models are discussed.

  DOI：

  10.1021/jm00117a008

文献信息

• Substituted benzamides with conformationally restricted side chains. 2. Indolizidine derivatives as central dopamine receptor antagonists
  作者：Frank D. King、Michael S. Hadley、Christine M. McClelland

  DOI：10.1021/jm00117a008

  日期：1988.9

  The substituted benzamides metoclopramide (1) and clebopride (3) are stimulants of gastric motility. They are also central dopamine receptor antagonists with 3 being the more potent. This is presumed to be due to an additional interaction of its N-benzyl group with the receptor. The effect of restricting the conformation of this group by replacing the N-benzylpiperidine side chain of 3 by phenyl-substituted quinolizidines and indolizidines has been investigated. Only the indolizidines had significant activity, the nature of which depended upon the orientation of the phenyl substituent. The 2 alpha-phenyl isomers 5d-h were potent central dopamine D2 receptor antagonists with 5h showing selectivity for the limbic system. The 2 beta-phenyl isomer 5c was a gastric motility stimulant devoid of significant central dopamine receptor antagonist activity. Implications on receptor models are discussed.