1-(4-溴-3-甲基苯基)吡咯烷-2-酮 | 197450-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(4-溴-3-甲基苯基)吡咯烷-2-酮
• 英文名称: 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one
• 英文别名: SB-249930
• CAS: 197450-39-8
• 化学式: C₁₁H₁₂BrNO
• mdl: MFCD09942748
• 分子量: 254.126
• InChiKey: UHABBHGGYQEDDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  449.6±38.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-(4-溴-3-甲基苯基)吡咯烷-2-酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 21.08h， 生成 1-(3-methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phenyl)pyrrolidin-2-one
  参考文献：
  名称：

  [EN] ARYL-BIPYRIDINE AMINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS
  [FR] DÉRIVÉS D'AMINE ARYL-BIPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE

  摘要：

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，其化学式为（I）：其中A、X、Y、Z、Q、R1、R2、R3、R4、R5和n如本文所述。

  公开号：

  WO2019126733A1
• 作为产物：
  描述：

  4-溴-3-甲基苯胺 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 1-(4-溴-3-甲基苯基)吡咯烷-2-酮
  参考文献：
  名称：

  Multikilogram-Scale Synthesis of a Biphenyl Carboxylic Acid Derivative Using a Pd/C-Mediated Suzuki Coupling Approach

  摘要：

  Reaction of 4-bromo-3-methylanaine with 4-chlorobutyryl chloride/TEA and subsequent treatment of the resulting secondary amide intermediate with KOt-Bu gives 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one in 65% yield, This procedure has been optimised (74-76% overall yield) and has been carried out on 41 molar scale. In a variation of this process, we have employed NaOH as the ring-closing base under phase-transfer conditions, NaOH is added to a mixture of 4-bromo-3-methylaniline, 4-chlorobutyryl chloride, and catalytic TBAC in THF/ H2O, A further 2 equiv of aqueous NaOH is added, and the mixture is heated at 40-45 degrees C, providing access to cyclised product In an improved 86% yield. 1-(4-Bromo-3-methylphenyl)pyrrolidin-2-one is subsequently coupled with 4-carboxyphenylboronic acid under standard Suzuki coupling conditions [Pd(PPh3)(4), Na2CO3, DME/H2O] to give 2'-methyl-4'-(2-oxo-1-pyrrolidinyl)biphenyl-4-carboxylic acid in 64% yield, contaminated with 40-80 ppm of residual Pd, In a modification of this process, we have used Pd/C as the catalyst, Reaction in MeOH/ H2O gives an improved yield of the biphenylcarboxyiic acid with residual Pd levels of <6 ppm, This process has been carried out on 24 molar scale, The synthesis of the arylpyrrolidinone and subsequent Suzuki coupling have been combined into a one-pot procedure, providing access to 2'-methyl-4'-(2-oxo-1-pyrrolidinyl)biphenyl-4-carboxylic acid in 82% overall yield from 4-bromo-3-methylaniline.

  DOI：

  10.1021/op980079g

文献信息

• [EN] AMINOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'AMINOPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE
  申请人：PETRA PHARMA CORP

  公开号：WO2019126731A1

  公开（公告）日：2019-06-27

  The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula: (I) where A, B, R1, X1, X2, and W are described herein.

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，其化学式为：(I)，其中A、B、R1、X1、X2和W如本文所述。
• Tetracyclic spiro compounds as 5HT.sub.1B receptor antagonists
  申请人：SmithKline Beecham p.l.c.

  公开号：US06100272A1

  公开（公告）日：2000-08-08

  Compounds of formula(I) where B is oxygen or sulphur, D is nitrogen, R.sup.6 and R.sup.7 forms a ring, m is 2, R is a substituted latam ring of formula (i) ##STR1## where p is 1, P is a substituted or unsubstituted bicyclic ring containing one or two heteroatoms or P is an unsbustituted or substituted 5- to 7-memebered saturated ring containing one or two heteroatoms; X, Y, Z, E, G, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, and R.sup.10 are as defined in the specification.

  化合物的化学式(I)，其中B为氧或硫，D为氮，R.sup.6和R.sup.7形成一个环，m为2，R为公式(i)的取代的拉丹环：##STR1## 其中p为1，P为含有一个或两个杂原子的取代或未取代的双环环或P为未取代或取代的含有一个或两个杂原子的5-至7-成员饱和环；X、Y、Z、E、G、R.sup.3、R.sup.4、R.sup.5、R.sup.8、R.sup.9和R.sup.10如规范所定义。
• Spiroazabicyclic compounds, processes for their preparation, and their
  申请人：SmithKline Beecham p.l.c.

  公开号：US06156783A1

  公开（公告）日：2000-12-05

  Novel azabicyclic derivatives, processes for their preparation, pharmaceutical compositions containing them and their use as medicaments are disclosed.

  本发明揭示了新型的杂环丙烷衍生物，以及制备它们的方法、含有它们的药物组合物以及它们作为药物的用途。
• α‐Angelica Lactone Catalyzed Oxidation of Pyrrolidines to Lactams
  作者：Siddharth K. Deepake、Manish Kumar、Pawan Kumar、Utpal Das

  DOI：10.1002/ejoc.202200712

  日期：2022.8.19

  An efficient method for the direct oxidation of various N-aryl pyrrolidines to the corresponding lactams using α- angelica lactone as catalyst has been demonstrated. Di-oxygen was employed as the terminal oxidant and oxygen source.

  已经证明了使用α-当归内酯作为催化剂将各种N-芳基吡咯烷直接氧化成相应内酰胺的有效方法。双氧被用作末端氧化剂和氧源。
• Scavenging and Reclaiming Phosphines Associated with Group 10 Metal-Mediated Couplings
  作者：Bruce H. Lipshutz、Bryan Frieman、Henrik Birkedal

  DOI：10.1021/ol049681j

  日期：2004.7.1

  Exposure of any of several mono- or bidentate phosphines to CuCl leads to quick removal of unwanted ligands from solution. Most phosphines, if desired, can be easily recovered.