N-(furan-2-ylmethyl)benzenesulfonamide | 4392-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(furan-2-ylmethyl)benzenesulfonamide
• 英文别名: N-(2-furylmethyl)benzenesulfonamide
• CAS: 4392-53-4
• 化学式: C₁₁H₁₁NO₃S
• mdl: MFCD00686902
• 分子量: 237.279
• InChiKey: XBKYSJYBCSCYCW-UHFFFAOYSA-N

物化性质

• 沸点：
  389.8±44.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(furan-2-ylmethyl)benzenesulfonamide 在 甲醇 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 N-(furan-2-ylmethyl)-N-(2-hydroxy-2-phenylbut-3-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles

  摘要：

  一种由金催化的呋喃底物1,2-酰氧迁移/分子内环丙烷化/环扩大级联反应提供了一种新的高效程序，用于形成十元环和十一元环化合物。报道了一种由金催化剂催化的分子间呋喃化合物的新转化类型。

  DOI：

  10.1039/c5cc05808b
• 作为产物：
  描述：

  苯磺酰胺 在 sodium tetrahydroborate 、 硅酸四乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 N-(furan-2-ylmethyl)benzenesulfonamide
  参考文献：
  名称：

  A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles

  摘要：

  一种由金催化的呋喃底物1,2-酰氧迁移/分子内环丙烷化/环扩大级联反应提供了一种新的高效程序，用于形成十元环和十一元环化合物。报道了一种由金催化剂催化的分子间呋喃化合物的新转化类型。

  DOI：

  10.1039/c5cc05808b

文献信息

• Steric promotion of cyclization reactions: Substituent effect studies in the furan intramolecular diels-alder reaction
  作者：Brian J. Mcnelis、Jeremy T. Starr、Hung Dang

  DOI：10.1002/jhet.5570350649

  日期：1998.11

  ide compounds have been synthesized and their rates of cyclization and equilibrium product concentrations determined. Increased steric bulk on the sulfonamide substituent has been shown to increase both the rate of cyclization and yields of these reactions. A three-fold increase in rate and 15% increase in yield was observed as the substituent was varied from methyl to triisopropylbenzene.

  已经合成了七个烷基和芳基取代的N-烯丙基-N-（甲基呋喃）-磺酰胺化合物，并确定了它们的环化速率和平衡产物浓度。磺酰胺取代基上增加的空间体积已显示出增加了这些反应的环化速率和产率。当取代基从甲基变为三异丙基苯时，观察到速率提高了三倍，收率提高了15％。
• Efficient and Practical Synthesis of Sulfonamides Utilizing SO₂ Gas Generated On Demand
  作者：Gulice Yiu Chung Leung、Balamurugan Ramalingam、Gabriel Loh、Anqi Chen

  DOI：10.1021/acs.oprd.9b00552

  日期：2020.4.17

  A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.
• Palladium catalysed synthesis of spiroindolines.
  作者：Ronald Grigg、Paul Fretwell、Clive Meerholtz、Visuvanathar Sridharan

  DOI：10.1016/s0040-4020(01)80760-2

  日期：1994.1

  A series of palladium catalysed consecutive bis(5-exo trig)-, 5-exo trig-6-exo trig-, and 5-exo trig-7-endo trig-cyclisations via an alkene relay onto benzene or a wide range of heterocycles (pyrrole, furan, thiophen, indole, pyridine, pyridones) generates 5,5-, 5,6- and 5,7-spiroindolines in good yield.
• Synthesis of <i>N</i>-Acyl-5-aminopenta-2,4-dienals via Base-Induced Ring-Opening of <i>N</i>-Acylated Furfurylamines: Scope and Limitations
  作者：Cécile Ouairy、Patrick Michel、Bernard Delpech、David Crich、Christian Marazano

  DOI：10.1021/jo100634z

  日期：2010.6.18

  N-Acylation of furfurylamines provided 1, which on double deprotonation with LDA led to the formation of N-acyl-5-aminopenta-2,4-dienals 2 via an isomerization involving opening of the furan ring. The scope and limitations of the procedure were examined by considering the influence of substituents on the carbonyl group and also on the heterocycle moiety. The efficacy of the reaction was shown to be very dependent on the nature of these groups.
• A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles
  作者：Yin-Wei Sun、Xiang-Ying Tang、Min Shi

  DOI：10.1039/c5cc05808b

  日期：——

  A gold catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade of furan substrates provides a new highly efficient procedure for the formation of ten and eleven-membered ring compounds. A new transformation type of intermolecular furan compound catalyzed by a gold catalyst was reported.

  一种由金催化的呋喃底物1,2-酰氧迁移/分子内环丙烷化/环扩大级联反应提供了一种新的高效程序，用于形成十元环和十一元环化合物。报道了一种由金催化剂催化的分子间呋喃化合物的新转化类型。