N-苄基-5-溴-2-糠酰胺 | 117845-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-苄基-5-溴-2-糠酰胺
• 英文名称: 5-bromofuran-2-carboxylic acid benzylamide
• 英文别名: N-benzyl-5-bromofuran-2-carboxamide
• CAS: 117845-23-5
• 化学式: C₁₂H₁₀BrNO₂
• mdl: MFCD00454467
• 分子量: 280.121
• InChiKey: DUZGNGADSRKPPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苄基-5-溴-2-糠酰胺 在 sodium hydroxide 、 (n-Bu₄)HSO₄ 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 61.0h， 生成 3-benzyl-7-bromo-5-methyl-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-en-2-one
  参考文献：
  名称：

  Intramolecular Cyclization Reactions of 5-Halo- and 5-Nitro-Substituted Furans

  摘要：

  [GRAPHICS]Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro-substituted furfuryl amide 33b underwent an unusual isomerization-cyclization reaction under microwave conditions to provide 1,4-dihydro-2H-benzo[4,5]furo[2,3-c]pyridin-3-one 34.

  DOI：

  10.1021/ol035233k
• 作为产物：
  描述：

  5-溴-2-糠酸 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-苄基-5-溴-2-糠酰胺
  参考文献：
  名称：

  Intramolecular Cyclization Reactions of 5-Halo- and 5-Nitro-Substituted Furans

  摘要：

  [GRAPHICS]Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro-substituted furfuryl amide 33b underwent an unusual isomerization-cyclization reaction under microwave conditions to provide 1,4-dihydro-2H-benzo[4,5]furo[2,3-c]pyridin-3-one 34.

  DOI：

  10.1021/ol035233k

文献信息

• High-Load, Soluble Oligomeric Carbodiimide:  Synthesis and Application in Coupling Reactions
  作者：Mianji Zhang、Punitha Vedantham、Daniel L. Flynn、Paul R. Hanson

  DOI：10.1021/jo048870c

  日期：2004.11.1

  A facile preparation of a high-load, soluble oligomeric alkyl cyclohexylcarbodiimide (OACC) reagent via ROM polymerization from commercially available starting materials is described. This reagent is exploited as a coupling reagent for esterification, amidation, and dehydration of carboxylic acids (aliphatic and aromatic) with an assortment of alcohols (aliphatic primary, secondary, and benzylic),

  描述了通过ROM聚合由市售的起始原料容易地制备高负荷的可溶性低聚烷基环己基碳二亚胺（OACC）试剂的方法。该试剂被用作偶联试剂，用于将羧酸（脂族和芳族）与各种醇（脂族伯，仲和苄基），硫醇，酚和胺（脂族伯，仲，分别是苄基和芳族/苯胺）。偶合事件发生后，用适当的溶剂（Et 2 O，MeOH或EtOAc）沉淀，然后通过SPE过滤，可提供具有极佳收率和纯度的产物。
• [EN] HETEROCYCLIC COMPOUNDS USEFUL AS MK2 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILES COMME INHIBITEURS DE MK2
  申请人：NOVARTIS AG

  公开号：WO2009010488A1

  公开（公告）日：2009-01-22

  The present invention describes tetracyclic compounds of formula (IA) or (IB), wherein the symbols R, X, A, Y, R2, R3 and D are as defined in the specification, their use in the treatment of certain diseases, e.g. depending on MK-2 or TNF activity, and ways of manufacturing them.

  本发明描述了式（IA）或（IB）的四环化合物，其中符号R、X、A、Y、R2、R3和D如规范中所定义，它们在治疗某些疾病中的用途，例如取决于MK-2或TNF活性，并制造它们的方法。
• Halo Substituent Effects on Intramolecular Cycloadditions Involving Furanyl Amides
  作者：Albert Padwa、Kenneth R. Crawford、Christopher S. Straub、Susan N. Pieniazek、K. N. Houk

  DOI：10.1021/jo0602322

  日期：2006.7.1

  Intramolecular Diels−Alder reactions involving a series of N-alkenyl-substituted furanyl amides were investigated. Stable functionalized oxanorbornenes were formed in high yield upon heating at 80−110 °C. The cycloaddition reactions include several bromo-substituted furanyl amides, and these systems were found to proceed at a much faster rate and in higher yield than without substitution. This effect

  涉及一系列N的分子内Diels-Alder反应研究了-烯基取代的呋喃酰胺。在80-110°C加热时，高产率形成稳定的官能化氧杂降冰片烯。环加成反应包括几种溴取代的呋喃酰胺，与未取代的反应相比，发现这些系统以更快的速率和更高的收率进行反应。通过在呋喃环的3或5位掺入卤素可以观察到这种效果，并且这种效果很普遍。已经用量子力学计算研究了卤素取代的呋喃的环加成率增加的原因。这些反应的成功归因于反应放热的增加。这既降低了活化焓，又增加了逆向加成的障碍。呋喃上的卤素取代会增加反应物能量并稳定产品，
• Tetracyclic Lactame Derivatives
  申请人：Schlapbach Achim

  公开号：US20090098218A1

  公开（公告）日：2009-04-16

  The present invention describes tetracyclic compounds of formula (IA) or (IB), wherein the symbols R, X, A, Y, R2, R3 and D are as defined in the specification, their use in the treatment of certain diseases, e.g. depending on MK-2 or TNF activity, and ways of manufacturing them.

  本发明描述了式（IA）或（IB）的四环化合物，其中符号R，X，A，Y，R2，R3和D如规范所定义，在治疗某些疾病（例如，取决于MK-2或TNF活性）中使用它们，并制造它们的方法。
• Rai, Usha Kumari; Mishra, S K; Shanker, Brija, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 618 - 623
  作者：Rai, Usha Kumari、Mishra, S K、Shanker, Brija、Singh, Sujan、Rao, R Balaji

  DOI：——

  日期：——