4-methyl-N-(3-methylbut-2-enyl)-N-phenylbenzenesulfonamide | 132704-03-1

• 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: 4-methyl-N-(3-methylbut-2-enyl)-N-phenylbenzenesulfonamide
• 英文别名: 4-methyl-N-(3-methylbut-2-enyl)l-N-penylbenzenesulfonamide；N-(3-methyl-but-2-enyl)-toluene-4-sulfonanilide；N-(3-Methyl-but-2-enyl)-toluol-4-sulfonanilid；4-Methyl-N-(3-methylbut-2-en-1-yl)-N-phenylbenzene-1-sulfonamide
• CAS: 132704-03-1
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: UZXKKLDGMFYUKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3-methylbut-2-enyl)-N-phenylbenzenesulfonamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到对甲苯硫酰苯胺
  参考文献：
  名称：

  Methylprenyl and Prenyl Protection for Sulfonamides

  摘要：

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.

  DOI：

  10.1055/s-0034-1379428
• 作为产物：
  描述：

  对甲苯硫酰苯胺 、 1-溴-3-甲基-2-丁烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以61%的产率得到4-methyl-N-(3-methylbut-2-enyl)-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Methylprenyl and Prenyl Protection for Sulfonamides

  摘要：

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.

  DOI：

  10.1055/s-0034-1379428

文献信息

• Development, Synthesis, and in silico Investigations of Novel Acyclic Allyl Fluoride Derivatives
  作者：Vaneet Saini、Nishita Chauhan、Harjinder Singh、Kamal Nain Singh、Jeffrey M. McKenna

  DOI：10.1055/a-1961-8013

  日期：2023.3

  A one step electrophilic fluorination of alkenes is reported, which furnishes the products in a highly regioselective manner via allylic rearrangement. The reaction proceeds efficiently under mild conditions with the use of trisubstituted alkenes as olefin partner and Selectfluor as an electrophilic fluorinating agent without the need of any transition metal catalyst or pre-functionalized substrates

  报道了烯烃的一步亲电氟化，通过烯丙基重排以高度区域选择性的方式提供产品。该反应在温和条件下有效进行，使用三取代烯烃作为烯烃伙伴，使用 Selectfluor 作为亲电氟化剂，无需任何过渡金属催化剂或预官能化底物。新合成化合物的虚拟筛选显示了它们通过抑制原卟啉原氧化酶 (PPO) 作为除草剂的潜在应用。
• Muehlstaedt, Manfred; Hollmann, Kerstin; Franke, Heike, Zeitschrift fur Chemie, 1990, vol. 30, # 8, p. 282 - 283
  作者：Muehlstaedt, Manfred、Hollmann, Kerstin、Franke, Heike

  DOI：——

  日期：——
• MUHLSTADT, MANFRED;HOLLMANN, KERSTIN;FRANKE, HEIKE, Z. CHEM., 30,(1990) N, C. 282-283
  作者：MUHLSTADT, MANFRED、HOLLMANN, KERSTIN、FRANKE, HEIKE

  DOI：——

  日期：——
• Methylprenyl and Prenyl Protection for Sulfonamides
  作者：Aigars Jirgensons、Anna Nikitjuka、Aleksandra Nekrasova

  DOI：10.1055/s-0034-1379428

  日期：——

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.