N-(thiophen-2-ylmethylene)-benzenesulfonamide

• 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-(thiophen-2-ylmethylene)-benzenesulfonamide
• 英文别名: N-[(E)-thiophen-2-ylmethylidene]benzenesulfonamide；(NE)-N-(thiophen-2-ylmethylidene)benzenesulfonamide
• 化学式: C₁₁H₉NO₂S₂
• 分子量: 251.33
• InChiKey: NGJBTQLCODSBAU-FMIVXFBMSA-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：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(thiophen-2-ylmethylene)-benzenesulfonamide 、 2-丁炔 在 Ir(cod)2BARF 、 三苯基乙酸 氢气 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (E)-N-(2-methyl-1-thiophen-2-yl-but-2-enyl)-benzenesulfonamide 、 (Z)-N-(2-methyl-1-thiophen-2-yl-but-2-enyl)-benzenesulfonamide
  参考文献：
  名称：

  Allylic Amines via Iridium-Catalyzed C−C Bond Forming Hydrogenation:  Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents

  摘要：

  Exposure of aromatic, heteroaromatic, and aliphatic N-arylsulfonyl aldimines 1a-12a in toluene solution at 60 degrees C to 2-butyne and hydrogen at ambient pressure in the presence of a cationic iridium(I) catalyst modified by BIPHEP enables formation of reductive coupling products, allylic amines 1b-12b, in good isolated yields as single geometrical isomers (> 95:5, E:Z). The nonsymmetric alkynes 4-methyl-2-pentyne couple to imines 1b-12b under standard conditions with complete levels of regioselection. Hydrogenative coupling of 2-hexyne to imines 6a, 12a, and 13a delivers allylic amines 15b, 16b, and 18b in 10:1 regioisomeric ratios in each case. As revealed by H-2 NMR analysis, reductive coupling of 2-butyne to imine 2a under an atmosphere of elemental deuterium provides deuterio-2b, which incorporates deuterium at the vinylic position (83% H-2) and at the allylic methyl groups (5% H-2). An equal distribution of deuterium at the allylic methyl groups suggests H-D exchange at the propargylic positions of 2-butyne in advance of C-C coupling.

  DOI：

  10.1021/ja073018j
• 作为产物：
  描述：

  苯磺酰胺 在 potassium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.0h， 生成 N-(thiophen-2-ylmethylene)-benzenesulfonamide
  参考文献：
  名称：

  通过机械化学从苯甲醇衍生物和亚氨基碘烷中无金属合成 N-磺酰亚胺

  摘要：

  据报道，通过在球磨设备 (RETSCH 400™) 中使亚氨基碘与大量芳基/杂芳基苯甲醇在 5 mL 的球磨设备 (RETSCH 400™) 中反应，实现了芳基/杂芳基 N-磺酰亚胺的方便且操作方便的机械化学合成。不锈钢（SS）反应罐。CHCl 3 ( η = 0.2–0.4 μL mg -1 ) 用作液体辅助研磨（LAG）辅助剂。这种使用标称量溶剂（如 LAG）的无金属催化剂和无碱合成证明了亚氨基碘烷的有效N-磺酰基转移反应，以中等至良好的产率提供所需的化合物。取代N-磺酰亚胺作为独立的天然产物结构单元和药物中间体以及磺酰胺的前体至关重要，磺酰胺已参与许多治疗计划中潜在的小分子治疗。基于控制反应和 DFT 计算讨论了假定的转化机制。

  DOI：

  10.1039/d3ob00791j

文献信息

• Eco-friendly and efficient catalyst-free synthesis of <i>N</i>-sulfonylimines from sulfonamides and aldehydes: crucial role of Al₂O₃ as a reusable dehydrating agent
  作者：Zaineb Litim、Hanen Slimi、Thierry Ollevier、Jamil Kraïem

  DOI：10.1039/d2ra08304c

  日期：——

  A green synthesis of N-sulfonylimines was developed involving the straightforward condensation of sulfonamides with aldehydes under green and catalyst-free conditions, mediated by neutral Al₂O₃ as an efficient and reusable dehydrating agent.

  开发了一种绿色合成N-磺酰亚胺的方法，该方法涉及在无催化剂的条件下，通过中性Al2O3作为高效和可重复使用的脱水剂，直接将磺酰胺与醛缩合。
• Allylic Amines via Iridium-Catalyzed C−C Bond Forming Hydrogenation:  Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents
  作者：Andriy Barchuk、Ming-Yu Ngai、Michael J. Krische

  DOI：10.1021/ja073018j

  日期：2007.7.1

  Exposure of aromatic, heteroaromatic, and aliphatic N-arylsulfonyl aldimines 1a-12a in toluene solution at 60 degrees C to 2-butyne and hydrogen at ambient pressure in the presence of a cationic iridium(I) catalyst modified by BIPHEP enables formation of reductive coupling products, allylic amines 1b-12b, in good isolated yields as single geometrical isomers (> 95:5, E:Z). The nonsymmetric alkynes 4-methyl-2-pentyne couple to imines 1b-12b under standard conditions with complete levels of regioselection. Hydrogenative coupling of 2-hexyne to imines 6a, 12a, and 13a delivers allylic amines 15b, 16b, and 18b in 10:1 regioisomeric ratios in each case. As revealed by H-2 NMR analysis, reductive coupling of 2-butyne to imine 2a under an atmosphere of elemental deuterium provides deuterio-2b, which incorporates deuterium at the vinylic position (83% H-2) and at the allylic methyl groups (5% H-2). An equal distribution of deuterium at the allylic methyl groups suggests H-D exchange at the propargylic positions of 2-butyne in advance of C-C coupling.
• Metal-free synthesis of <i>N</i>-sulfonyl imines from benzyl alcohol derivatives and iminoiodinanes <i>via</i> mechanochemistry
  作者：Souvik Guha、Ritwik Bhattacharya、Jesni Jacob、Mahesh Ravva、Subhabrata Sen

  DOI：10.1039/d3ob00791j

  日期：——

  mechanochemical synthesis of aryl/heteroaryl N-sulfonyl imines is reported by reacting iminoiodinanes with numerous aryl/heteroaryl benzyl alcohols in ball milling apparatus (RETSCH 400™) with three 5 mm stainless steel (ss) balls in a 5 mL stainless steel (ss) reaction jar. CHCl3 (η = 0.2–0.4 μL mg−1) was used as a liquid assisted grinding (LAG) auxiliary. This metal catalyst- and base- free synthesis with nominal

  据报道，通过在球磨设备 (RETSCH 400™) 中使亚氨基碘与大量芳基/杂芳基苯甲醇在 5 mL 的球磨设备 (RETSCH 400™) 中反应，实现了芳基/杂芳基 N-磺酰亚胺的方便且操作方便的机械化学合成。不锈钢（SS）反应罐。CHCl 3 ( η = 0.2–0.4 μL mg -1 ) 用作液体辅助研磨（LAG）辅助剂。这种使用标称量溶剂（如 LAG）的无金属催化剂和无碱合成证明了亚氨基碘烷的有效N-磺酰基转移反应，以中等至良好的产率提供所需的化合物。取代N-磺酰亚胺作为独立的天然产物结构单元和药物中间体以及磺酰胺的前体至关重要，磺酰胺已参与许多治疗计划中潜在的小分子治疗。基于控制反应和 DFT 计算讨论了假定的转化机制。