methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate | 345891-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate
• CAS: 345891-27-2
• 化学式: C₇H₅Br₃O₃
• 分子量: 376.827
• InChiKey: JBQCDOKUUNNZKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate 在 吡啶 、 水 作用下， 反应 1.33h， 以87%的产率得到methyl 2-bromo-5-formylfuran-4-carboxylate
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.030
• 作为产物：
  描述：

  2-甲基-3-糠酸甲酯 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， 以72%的产率得到methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate
  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
• gem-Dibromomethylarenes as Aldehyde Surrogates in the Pictet-Spengler Synthesis of Tetrahydroisoquinolines and Isoindoloisoquinolones
  作者：John Augustine、Nagaraja Chowdappa、Bailur Sherigara、Kummara Areppa、Ashis Mandal

  DOI：10.1055/s-0030-1258137

  日期：2010.9

  A new variant of the Pictet-Spengler reaction has been developed using gem-dibromomethylarenes as aldehyde surrogates to afford a variety of tetrahydroisoquinoline and isoindoloisoquinolone ring systems in good yields. These systems comprise important motifs in naturally occurring bioactive substances.

  使用偕二溴甲基芳烃作为醛替代物开发了一种新的 Pictet-Spengler 反应变体，以良好的产率提供各种四氢异喹啉和异吲哚并异喹诺酮环系统。这些系统包含天然存在的生物活性物质中的重要基序。
• On the bromination of methyl 2-methyl-3-furoate
  作者：Haripada Khatuya

  DOI：10.1016/s0040-4039(01)00275-1

  日期：2001.4

  Methyl 2-methyl-3-furoate was subjected to bromination with N-bromosuccinimide (NBS), a milder brominating reagent, under different reaction conditions to obtain a variety of selective brominated products.

  用较温和的溴化试剂N-溴琥珀酰亚胺（NBS）在不同的反应条件下对2-糠酸3-甲基糠酯进行溴化反应，得到各种选择性的溴化产物。
• A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes
  作者：John Kallikat Augustine、Y. Arthoba Naik、Ashis Baran Mandal、Nagaraja Chowdappa、Vinuthan B. Praveen

  DOI：10.1016/j.tet.2007.11.030

  日期：2008.1

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.
• <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.