2,2-di-phenyl-4-(2-azabicyclo[2. 2. 2]oct-2-yl)butyronitrile | 57726-63-3

• 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: 2,2-di-phenyl-4-(2-azabicyclo[2. 2. 2]oct-2-yl)butyronitrile
• 英文别名: 4-(2-aza-bicyclo[2.2.2]oct-2-yl)-2,2-diphenyl-butyronitrile；2,2-diphenyl-4-(2-azabicyclo[2.2.2]octan-2-yl)butanenitrile；2,2-diphenyl-4-(2-azabicyclo[2.2.2.]oct-2-yl)butyronitrile；2,2-diphenyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile；4-(2-azabicyclo[2.2.2]octan-2-yl)-2,2-diphenylbutanenitrile
• CAS: 57726-63-3
• 化学式: C₂₃H₂₆N₂
• 分子量: 330.473
• InChiKey: WPCNGJRDRUQERM-UHFFFAOYSA-N

物化性质

• 熔点：
  96-99 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  496.6±45.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-di-phenyl-4-(2-azabicyclo[2. 2. 2]oct-2-yl)butyronitrile 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-(3-[1,3,4]oxadiazol-2-yl-3,3-diphenyl-propyl)-2-aza-bicyclo[2.2.2]octane
  参考文献：
  名称：

  3,3-Diphenyl-3-(2-alkyl-1,3,4-oxadiazol-5-yl)propylcycloalkylamines, a novel series of antidiarrheal agents

  摘要：

  A series of 4-amino-2,2-diarylbutyronitriles (3) prepared for testing as inhibitors of gastrointestinal propulsive activity did not show any enhancement over such existing agents as diphenoxylate and loperamide. However, conversion of the nitrile group to a 2-methyl-1,3,4-oxadiazol-5-yl function led to compounds 5g and 5j, statistically equipotent to diphenoxylate and loperamide in the mouse and showing a very low order of analgesic activity. Structural modifications determined that the best separation of antipropulsive and analgesic effects was obtained when the amino group was bicyclic and the oxadiazole ring had a 2-methyl substituent. The most potent compounds were and analogues of diphenoxylate and loperamide where the oxadiazole ring was present, but these compounds had marked analgesic activity.

  DOI：

  10.1021/jm00232a010
• 作为产物：
  描述：

  溴乙基二苯乙腈 、 3-氮杂双环[2.2.2]辛烷盐酸盐 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 以83.5%的产率得到2,2-di-phenyl-4-(2-azabicyclo[2. 2. 2]oct-2-yl)butyronitrile
  参考文献：
  名称：

  Process for the preparation of tertiary amines

  摘要：

  某些作为药物有用的三级胺，通过在水性介质中在酸受体的存在下，将环状二级胺与一级烷基卤化物缩合，以提高产量制备。

  公开号：

  US04086234A1

文献信息

• 2-Azabicyclo[2.2.2.]octan-2-yl-diphenyl-alkanones and related compounds
  申请人：G. D. Searle & Co.

  公开号：US04028364A1

  公开（公告）日：1977-06-07

  This invention encompasses novel 2-azabicyclo[2.2.2]-octan-2-yl-diphenyl-alkanones and related compounds. These compounds are useful as anti-diarrheal agents.

  这一发明涵盖了新型的2-azabicyclo[2.2.2]-辛烷-2-基二苯基烷酮及相关化合物。这些化合物可用作抗腹泻药物。
• Anti-diarrheal oxadiazoles
  申请人：G. D. Searle & Co.

  公开号：US04003904A1

  公开（公告）日：1977-01-18

  The present invention encompasses a compound of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein Y is alkylene having 1-4 carbon atoms; R.sub.1 and R.sub. 2 together with N is a heterocyclic ring system consisting of an azamonocyclic ring of the formula ##STR2## wherein Z is oxygen, methylene, phenylhydroxymethylene, phenylcarboxymethylene or, phenylloweralkoxymethylene, or an azabicycloalkane structure having 6-9 carbon atoms and having at least 5 atoms in each ring of the azabicycloalkane structure; X is hydrogen, halogen, loweralkyl having 1-7 carbon atoms, or loweralkoxy having 1-7 carbon atoms; and Ar is phenyl, pyridyl, or monosubstituted phenyl wherein the substituent is halogen, loweralkyl having 1-7 carbon atoms, or loweralkoxy having 1-7 carbon atoms when R.sub.3 is hydrogen or Ar is 3 or 4 pyridyl when R.sub.3 is lower alkyl having 1-7 carbon atoms. The compounds of the present invention are prepared by converting the corresponding nitriles to 1H-tetrazoles and in turn reacting the 1H-tetrazole with ethyl chloroglyoxylate, hydrolyzing the resulting ester to the acid and decarboxylation to provide compounds wherein R.sub.3 is hydrogen. Compounds of the present invention are anti diarrheal agents.

  本发明涵盖公式##STR1##的化合物及其药学上可接受的酸盐，其中Y是具有1-4个碳原子的烷基；R.sub.1和R.sub. 2与N一起是由公式##STR2##组成的杂环环系，其中Z是氧、亚甲基、苯基羟甲基、苯基羧甲基或苯基低烷氧基甲基，或者是具有6-9个碳原子并且在杂环环系的每个环中至少有5个原子的氮杂环庚烷结构；X是氢、卤素、具有1-7个碳原子的低烷基或具有1-7个碳原子的低烷氧基；Ar是苯基、吡啶基或单取代苯基，其中取代基是卤素、具有1-7个碳原子的低烷基或具有1-7个碳原子的低烷氧基，当R.sub.3是氢或Ar是3或4吡啶基时，取代基是具有1-7个碳原子的低烷基。本发明的化合物是通过将相应的腈转化为1H-四唑，然后与氯乙酰乙酯反应，水解得到酸，脱羧得到R.sub.3为氢的化合物制备的。本发明的化合物是抗腹泻剂。
• US4003904A
  申请人：——

  公开号：US4003904A

  公开（公告）日：1977-01-18
• US4028364A
  申请人：——

  公开号：US4028364A

  公开（公告）日：1977-06-07
• US4086234A
  申请人：——

  公开号：US4086234A

  公开（公告）日：1978-04-25