2-bromo-4-(dibromomethyl)pyridine | 865449-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-bromo-4-(dibromomethyl)pyridine
• 英文别名: 2-Bromo-4-(dibromomethyl)pyridine
• CAS: 865449-19-0
• 化学式: C₆H₄Br₃N
• 分子量: 329.816
• InChiKey: ALJYVMOESYZCBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(dibromomethyl)pyridine 在 calcium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以60%的产率得到2-溴吡啶-4-甲醛
  参考文献：
  名称：

  The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates

  摘要：

  A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.016
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 2-bromo-4-(dibromomethyl)pyridine
  参考文献：
  名称：

  gem-Dibromomethylarenes:  A Convenient Substitute for Noncommercial Aldehydes in the Knoevenagel−Doebner Reaction for the Synthesis of α,β-Unsaturated Carboxylic Acids

  摘要：

  [Graphics]A facile synthesis of alpha,beta-unsaturated carboxylic acids from gem-dibromomethylarenes is described. gem-Dibromomethylarenes are employed for the first time in the Knoevenagel-Doebner reaction as aldehyde equivalents for the efficient synthesis of alpha,beta-unsaturated carboxylic acids.

  DOI：

  10.1021/jo701888m

文献信息

• gem-Dibromomethyl Aromatics: Efficient Aldehyde Equivalents in the Knoevenagel-Doebner Reaction
  作者：John Augustine、Yanjerappa Naik、Subba Poojari、Nagaraja Chowdappa、Bailur Sherigara、Kummara Areppa

  DOI：10.1055/s-0029-1216849

  日期：2009.7

  efficient synthesis of cinnamic esters is described. This reaction provides cinnamic esters in a single step from gem-dibromomethyl aromatics, which otherwise require the hydrolytic conversion of gem-dibromides into aldehydes, and demonstrates the use of an alternative reagent for noncommercial and expensive aldehydes. Further, the reaction of gem-dibromomethyl aromatics with malonic acid and di-tert-butyl

  描述了有效合成肉桂酸酯的Knoevenagel-Doebner反应的有价值的变化。该反应在单个步骤中由宝石-二溴甲基芳族化合物提供肉桂酸酯，否则其需要将宝石-二溴化物水解转化为醛，并证明了用于非商业和昂贵醛的替代试剂的使用。此外，还描述了宝石-二溴甲基芳族化合物与丙二酸和二碳酸二叔丁酯的反应，用于一锅合成肉桂酸叔丁基酯。 Knoevenagel-Doebner反应-肉桂酸叔丁酯-宝石-二溴甲基芳族化合物-二碳酸二叔丁酯-水解
• One-pot synthesis of benzimidazoles from gem-dibromomethylarenes using o-diaminoarenes
  作者：Chandrappa Siddappa、Vinaya Kambappa、Ananda Kumar C. Siddegowda、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2010.09.080

  日期：2010.12

  A one-pot synthesis of benzimidazoles from gem-dibromomethylarenes is described. The reaction shows the method to prepare a variety of benzimidazole analogues with excellent yield.

  描述了从宝石-二溴甲基芳烃一锅合成苯并咪唑。该反应显示出以优异的产率制备各种苯并咪唑类似物的方法。
• One-pot approach for the synthesis of 2-aryl benzothiazoles via a two-component coupling of gem-dibromomethylarenes and o-aminothiophenols
  作者：Chandrappa Siddappa、Vinaya Kambappa、Muddegowda Umashankara、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2011.08.055

  日期：2011.10

  One-pot synthesis of 2-aryl benzothiazoles from gem-dibromomethylarenes using 2-aminoarylthiols is described. Benzothiazoles were obtained in high chemical yields under mild conditions. This transformation would facilitate synthesis by short reaction times, large-scale synthesis, easy and quick isolation of the products, which are the main advantages of this procedure. (C) 2011 Published by Elsevier Ltd.
• <i>gem</i>-Dibromomethylarenes:  A Convenient Substitute for Noncommercial Aldehydes in the Knoevenagel−Doebner Reaction for the Synthesis of α<i>,</i>β-Unsaturated Carboxylic Acids
  作者：John Kallikat Augustine、Yanjerappa Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1021/jo701888m

  日期：2007.12.1

  [Graphics]A facile synthesis of alpha,beta-unsaturated carboxylic acids from gem-dibromomethylarenes is described. gem-Dibromomethylarenes are employed for the first time in the Knoevenagel-Doebner reaction as aldehyde equivalents for the efficient synthesis of alpha,beta-unsaturated carboxylic acids.
• The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates
  作者：Ashis Baran Mandal、John Kallikat Augustine、Anna Quattropani、Agnes Bombrun

  DOI：10.1016/j.tetlet.2005.07.016

  日期：2005.9

  A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized. (c) 2005 Elsevier Ltd. All rights reserved.