(+/-)-4-(2',4'-dibromobutyrylamino)benzonitrile | 246136-28-7

• 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-(2',4'-dibromobutyrylamino)benzonitrile
• 英文别名: 4-(2,4-bromobutyrylamino)-benzonitrile；2,4-dibromo-N-(4-cyanophenyl)butanamide
• CAS: 246136-28-7
• 化学式: C₁₁H₁₀Br₂N₂O
• 分子量: 346.021
• InChiKey: WMFAHRZMHCTIFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(2',4'-dibromobutyrylamino)benzonitrile 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 4-(3-Amino-2-oxopyrrolidin-1-yl)benzonitrile
  参考文献：
  名称：

  An efficient asymmetric synthesis of (3S)-3-amino-1-(4-cyanophenyl)-2-oxopyrrolidine hydrochloride salt

  摘要：

  Reaction of 4-aminobenzonitrile with 2-bromo-4-chlorobutyryl bromide in the presence of sodium phosphate followed by treatment of the coupled product with sodium hydroxide followed by ammonium hydroxide in acetonitrile yielded the title compound as the racemic (R)-(-)-mandelic acid salt in an overall yield of 64%. The title compound was then obtained with an ee >96% and in 78% yield after a dynamic resolution of the racemic salt in IPA using a catalytic amount of salicylaldehyde followed by salt exchange. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00260-2
• 作为产物：
  描述：

  2,4-二溴丁酰溴 、 对氨基苯腈 在 sodium phosphate 作用下， 以 乙腈 为溶剂， 生成 (+/-)-4-(2',4'-dibromobutyrylamino)benzonitrile
  参考文献：
  名称：

  An efficient asymmetric synthesis of (3S)-3-amino-1-(4-cyanophenyl)-2-oxopyrrolidine hydrochloride salt

  摘要：

  Reaction of 4-aminobenzonitrile with 2-bromo-4-chlorobutyryl bromide in the presence of sodium phosphate followed by treatment of the coupled product with sodium hydroxide followed by ammonium hydroxide in acetonitrile yielded the title compound as the racemic (R)-(-)-mandelic acid salt in an overall yield of 64%. The title compound was then obtained with an ee >96% and in 78% yield after a dynamic resolution of the racemic salt in IPA using a catalytic amount of salicylaldehyde followed by salt exchange. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00260-2

文献信息

• Process for the preparation of a 2-oxopyrrolidine compound
  申请人：G. D. Searle & Co.

  公开号：US05986107A1

  公开（公告）日：1999-11-16

  A process for producing a lactam of the formula ##STR1## wherein 2-bromo-4 chloro butyryl bromide or 2,4-dibromo butyryl bromide is coupled with 4-aminobenzonitrile to produce 4-(2,4-bromobutyrylamino)-benzonitrile, which is combined with sodium hydroxide, potassium hydroxide or potassium carbonate to produce 4-(3-bromo-2-oxopyrrolidin-1-yl)benzonitrile which is subjected to an excess of ammonium hydroxide to produce compounds of the formula (I).

  生产一种公式为##STR1##的内酰胺的方法，其中2-溴-4-氯丁酰溴或2,4-二溴丁酰溴与4-氨基苯甲腈偶联，产生4-(2,4-溴丁酰氨基)-苯甲腈，然后与氢氧化钠、氢氧化钾或碳酸钾结合，产生4-(3-溴-2-氧代吡咯啉-1-基)苯甲腈，然后通过过量氢氧化铵处理，产生公式(I)的化合物。
• PROCESS FOR THE PREPARATION OF A 2-OXOPYRROLIDINE COMPOUND
  申请人：G.D. SEARLE & CO.

  公开号：EP1068183A2

  公开（公告）日：2001-01-17
• US5986107A
  申请人：——

  公开号：US5986107A

  公开（公告）日：1999-11-16
• [EN] PROCESS FOR THE PREPARATION OF A 2-OXOPYRROLIDINE COMPOUND<br/>[FR] PROCEDE DE PREPARATION D'UN COMPOSE DE 2-OXOPYRROLIDINE
  申请人：——

  公开号：WO1999051573A2

  公开（公告）日：1999-10-14

  [EN] A process for producing a lactam of formula (I).
  [FR] L'invention porte sur un procédé de production d'un lactame de formule (I).
• An efficient asymmetric synthesis of (3S)-3-amino-1-(4-cyanophenyl)-2-oxopyrrolidine hydrochloride salt
  作者：Pierre-Jean Colson、Claire A. Przybyla、Bruce E. Wise、Kevin A. Babiak、Lisa M. Seaney、Donald E. Korte

  DOI：10.1016/s0957-4166(98)00260-2

  日期：1998.8

  Reaction of 4-aminobenzonitrile with 2-bromo-4-chlorobutyryl bromide in the presence of sodium phosphate followed by treatment of the coupled product with sodium hydroxide followed by ammonium hydroxide in acetonitrile yielded the title compound as the racemic (R)-(-)-mandelic acid salt in an overall yield of 64%. The title compound was then obtained with an ee >96% and in 78% yield after a dynamic resolution of the racemic salt in IPA using a catalytic amount of salicylaldehyde followed by salt exchange. (C) 1998 Elsevier Science Ltd. All rights reserved.