2-(2,5-二溴苯基)乙腈 | 74533-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,5-二溴苯基)乙腈
• 中文别名: 2,5-二溴苯乙腈
• 英文名称: (2,5-dibromophenyl)acetonitrile
• 英文别名: 2-(2,5-Dibromophenyl)acetonitrile
• CAS: 74533-21-4
• 化学式: C₈H₅Br₂N
• 分子量: 274.942
• InChiKey: OWSYQAWIZWILQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  2-(2,5-二溴苯基)乙腈 在 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 、 copper(ll) bromide 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 38.0h， 生成 5-bromo-1-methoxy-2-oxindole
  参考文献：
  名称：

  Synthesis of N-Alkoxyindol-2-ones by Copper-Catalyzed Intramolecular N-Arylation of Hydroxamates

  摘要：

  首次展示了铜催化的羟胺衍生物的分子内部N-芳基化反应。基于这一转化，开发了一种从2-(2-溴芳基)乙酰羟胺酯合成N-烷氧基吲哚-2-酮的新方法。反应条件能够容忍羟胺部分的标准羟基保护基团，且同样适用于合成六元N-烷氧基苯内酰胺。

  DOI：

  10.1055/s-0030-1260328
• 作为产物：
  描述：

  2,5-二溴苯甲酸 在 氯化亚砜 、 硼烷四氢呋喃络合物 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.4h， 生成 2-(2,5-二溴苯基)乙腈
  参考文献：
  名称：

  Aminopyridine-Based c-Jun N-Terminal Kinase Inhibitors with Cellular Activity and Minimal Cross-Kinase Activity

  摘要：

  The c-Jun N-terminal kinases (JNK-1, -2, and -3) are members of the mitogen activated protein (MAP) kinase family of enzymes. They are activated in response to certain cytokines, as well as by cellular stresses including chemotoxins, peroxides, and irradiation. They have been implicated in the pathology of a variety of different diseases with an inflammatory component including asthma, stroke, Alzheimer's disease, and type 2 diabetes mellitus. In this work, high-throughput screening identified a JNK inhibitor with an excellent kinase selectivity profile. Using X-ray crystallography and biochemical screening to guide our lead optimization, we prepared compounds with inhibitory potencies in the low-double-digit nanomolar range, activity in whole cells, and pharmacokinetics suitable for in vivo use. The new compounds were over 1,000-fold selective for JNK-1 and -2 over other MAP kinases including ERK2, p38alpha, and p38delta and showed little inhibitory activity against a panel of 74 kinases.

  DOI：

  10.1021/jm060199b

文献信息

• Copper-catalysed synthesis of 3-hydroxyisoindolin-1-ones from benzylcyanide 2-iodobenzamides
  作者：Veerababurao Kavala、Chen-Yu Wang、Cheng-Chuan Wang、Prakash Bhimrao Patil、ChiaChi Fang、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1039/c9ob02329a

  日期：——

  An efficient one-pot two-step sequential reaction for the synthesis of biologically active 3-hydroxyisoindolin-1-one derivatives from 2-iodobenzamide derivatives and various substituted benzyl cyanides in the presence of CuCl and cesium carbonate in DMSO is reported. Furthermore, 3-hydroxyisoindolinone derivatives possessing bromo substituents were obtained from 2-iodobenzamide and 2-bromobenzyl cyanide

  报道了在DMSO中在CuCl和碳酸铯存在下从2-碘代联苯酰胺衍生物和各种取代的苄基氰化物合成生物活性的3-羟基异吲哚啉-1-酮衍生物的有效的一锅两步顺序反应。此外，从2-碘代苯甲酰胺和2-溴苄基氰化物底物分两步获得具有溴取代基的3-羟基异吲哚啉酮衍生物。氰化苄已首次成功地用作苯甲酰基合成子，用于合成3-羟基异吲哚啉-1-酮。有趣的是，3-羟基异吲哚-1-酮的形成机理是一种新的途径，涉及碳降解，然后发生环收缩。
• 一种2，5－二溴苯乙酸的合成方法
  申请人：南京工业大学

  公开号：CN107759459A

  公开（公告）日：2018-03-06

  本发明公开了一种抗丙肝药物中间体2，5‑二溴苯乙酸的合成。本发明以对二溴苯为原料，经氯甲基化，氰化，水解步骤得到2，5二溴苯乙酸。其中氯甲基化反应中以氯化钠为氯化试剂，多聚甲醛为原料，浓硫酸为溶剂和酸，和多聚甲醛反应生成2，5‑二溴苄氯。再用2，5‑二溴苄氯和氰化亚铜在DMF中回流反应得到2，5‑二溴苯乙腈。最后用2，5‑二溴苯乙腈在氢氧化钠水溶液中水解，再用盐酸酸化，得到产物2，5‑二溴苯乙酸。该发明具有成品低廉，反应条件温和等特点。
• One-Pot Synthesis of 2-(Aryl/Alkyl)amino-3-cyanobenzo[<i>b</i> ]thiophenes and Their Hetero-Fused Analogues by Pd-Catalyzed Intramolecular Oxidative C-H Functionalization/Arylthiolation
  作者：Bonagiri Saraiah、Vibha Gautam、Anand Acharya、Mohamed A. Pasha、Ila Hiriyakkanavar

  DOI：10.1002/ejoc.201700963

  日期：2017.10.10

  An efficient one-pot synthesis has been developed for substituted 2-(aryl/alkyl)amino-3-cyanobenzo[b]thiophenes and their hetero-fused analogues by using (hetero)arylacetonitriles and aryl/alkyl isothiocyanates in a PdII-catalyzed C–H functionalization/arylthiolation reaction. Some of the 2-arylamino-3-cyanobenzo[b]thiophenes were successfully converted into benzothieno[2,3-b]quinolones. DMSO = dimethyl

  通过在Pd II催化下使用（杂）芳基乙腈和芳基/烷基异硫氰酸酯，已开发出一种有效的一锅合成方法，用于取代的2-（芳基/烷基）氨基-3-氰基苯并[ b ]噻吩及其杂合类似物。C–H官能化/芳硫基化反应。一些2-芳基氨基-3-氰基苯并[ b ]噻吩已成功转化为苯并噻吩并[2,3- b ]喹诺酮。DMSO =二甲基亚砜；Tf =三氟甲磺酰基；DCE ＝ 1，2-二氯乙烷。
• 2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives
  作者：Peter B. Russell、George H. Hitchings

  DOI：10.1021/ja01152a060

  日期：1951.8
• Aminopyridine-Based c-Jun N-Terminal Kinase Inhibitors with Cellular Activity and Minimal Cross-Kinase Activity
  作者：Bruce G. Szczepankiewicz、Christi Kosogof、Lissa T. J. Nelson、Gang Liu、Bo Liu、Hongyu Zhao、Michael D. Serby、Zhili Xin、Mei Liu、Rebecca J. Gum、Deanna L. Haasch、Sanyi Wang、Jill E. Clampit、Eric F. Johnson、Thomas H. Lubben、Michael A. Stashko、Edward T. Olejniczak、Chaohong Sun、Sarah A. Dorwin、Kristi Haskins、Cele Abad-Zapatero、Elizabeth H. Fry、Charles W. Hutchins、Hing L. Sham、Cristina M. Rondinone、James M. Trevillyan

  DOI：10.1021/jm060199b

  日期：2006.6.1

  The c-Jun N-terminal kinases (JNK-1, -2, and -3) are members of the mitogen activated protein (MAP) kinase family of enzymes. They are activated in response to certain cytokines, as well as by cellular stresses including chemotoxins, peroxides, and irradiation. They have been implicated in the pathology of a variety of different diseases with an inflammatory component including asthma, stroke, Alzheimer's disease, and type 2 diabetes mellitus. In this work, high-throughput screening identified a JNK inhibitor with an excellent kinase selectivity profile. Using X-ray crystallography and biochemical screening to guide our lead optimization, we prepared compounds with inhibitory potencies in the low-double-digit nanomolar range, activity in whole cells, and pharmacokinetics suitable for in vivo use. The new compounds were over 1,000-fold selective for JNK-1 and -2 over other MAP kinases including ERK2, p38alpha, and p38delta and showed little inhibitory activity against a panel of 74 kinases.