benzothiazole-2-sulfonic acid phenylamide | 2743-86-4

• 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: benzothiazole-2-sulfonic acid phenylamide
• 英文别名: N-Phenyl-1,3-benzothiazole-2-sulfonamide；N-phenyl-1,3-benzothiazole-2-sulfonamide
• CAS: 2743-86-4
• 化学式: C₁₃H₁₀N₂O₂S₂
• 分子量: 290.367
• InChiKey: UCBKOOSQMPVLOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzothiazole-2-sulfonic acid phenylamide 、 1-bromo-2,3-dimethyl-2-butene 在 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以44%的产率得到N-(2,3-dimethylbut-2-enyl)l-N-penylbenzo[d]thiazole-2-sulfonamide
  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：

  N-(2,3-dimethylbut-2-enyl)l-N-penylbenzo[d]thiazole-2-sulfonamide 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91%的产率得到benzothiazole-2-sulfonic acid phenylamide
  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

• Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement
  作者：Catherine M. Holden、Shariar M. A. Sohel、Michael F. Greaney

  DOI：10.1002/anie.201510236

  日期：2016.2.12

  A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions

  描述了新的苯并炔转化，其提供通用的联芳基结构，而无需求助于过渡金属催化或化学计量的有机金属结构单元。芳基磺酰胺在氟化物活化后加至苯并，然后进行芳基Truce-Smiles重排，得到具有二氧化硫挤出的联芳基。该反应在简单的反应条件下进行，并且具有空间位阻阻转异构二芳基胺的合成的优异范围。
• Takahashi; Okada, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 277
  作者：Takahashi、Okada

  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.