3-bromo-1-(4-cyanophenyl)pyrrolidin-2-one | 213978-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-bromo-1-(4-cyanophenyl)pyrrolidin-2-one
• 英文别名: 4-(3-bromo-2-oxopyrrolidin-1-yl)benzonitrile
• CAS: 213978-36-0
• 化学式: C₁₁H₉BrN₂O
• mdl: MFCD01940901
• 分子量: 265.109
• InChiKey: WPIZASJVDDJWKA-UHFFFAOYSA-N

物化性质

• 沸点：
  498.6±40.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(4-cyanophenyl)pyrrolidin-2-one 在 ammonium hydroxide 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-bromo-4-chloro-N-(4-cyanophenyl)butanamide 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 3-bromo-1-(4-cyanophenyl)pyrrolidin-2-one
  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。
• Kinetics and mechanism of formation and decomposition of substituted 1-phenylpyrrolidin-2-ones in basic medium
  作者：Milos̆ Sedlák、Ludmila Hejtmánková、Pavla Kas̆parová、Jaromír Kaválek

  DOI：10.1002/poc.468

  日期：2002.3

  different derivatives and depend on the substituents in the aromatic and/or heterocyclic moiety. The rate-limiting step of hydrolysis of 1-(4-nitrophenyl)pyrrolidin-2-one consists of the non-catalysed decomposition of the tetrahedral intermediate. In the case of 3-bromo-1-(4-nitrophenyl)pyrrolidin-2-one at sodium hydroxide concentrations below 0.1 mol l−1, the rate-limiting step is the second reaction pathway

  对取代的4-氯-N-苯基丁酰胺在氢氧化钠水溶液中的化学行为的研究表明，底物首先进行闭环反应，得到取代的1-苯基吡咯烷二-2-酮，然后水解为4-钠的取代衍生物。氨基-N-苯基丁酸酯。动力学测量提供了在25°C水中2-溴-4-氯-N-（4-硝基苯基）丁酰胺的解离常数p K a和环化速率常数k c的值[p K a  = 11.64±0.01; k c  =（1.94±0.03）×10 -2 s -1 ]，4-氯-N-（4-硝基苯基）丁酰胺[p K a  = 13.35±0.02；k c  ＝（1.60±0.02）×10 -2 s -1 ]和4-氯-2-甲基-N-（4-硝基苯基）丁酰胺[p K a  ＝ 13.55±0.03；k c  ＝（7.61±0.11）×10 -2 s -1 ]。各个衍生物的p K a和k c值因丁酰胺骨架的α位取代而异。在甲醇钠甲醇溶液中，2-溴-4-氯-N的闭环过程-（
• 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).