(2-methoxybenzyl)(2-nitrobenzenesulfonyl)amine | 349099-29-2

• 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: (2-methoxybenzyl)(2-nitrobenzenesulfonyl)amine
• 英文别名: N-(2-methoxybenzyl)-2-nitrobenzenesulfonamide；N-[(2-methoxyphenyl)methyl]-2-nitrobenzenesulfonamide
• CAS: 349099-29-2
• 化学式: C₁₄H₁₄N₂O₅S
• 分子量: 322.342
• InChiKey: LRQUIWFKZCMXKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-methoxybenzyl)(2-nitrobenzenesulfonyl)amine 在 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 2-{[2-(2-Methoxy-benzylsulfamoyl)-phenylamino]-methylene}-malonic acid diethyl ester
  参考文献：
  名称：

  Sulfamoyl-4-oxoquinoline-3-carboxamides: Novel potentiators of defective ΔF508-cystic fibrosis transmembrane conductance regulator chloride channel gating

  摘要：

  The synthesis of a small collection of sulfamoyl-4-oxoquinoline-3-carboxamides is described for use as correctors of defective gating of the Delta F508-cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. Several compounds with submicromolar potency were obtained. N-Ethyl 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (7b) was found to be the most effective sulfonamide corrector of defective Delta F508-CFTR gating. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.050
• 作为产物：
  描述：

  邻甲氧基苄胺 、 邻硝基苯磺酰氯 在 TEA 作用下， 反应 1.0h， 生成 (2-methoxybenzyl)(2-nitrobenzenesulfonyl)amine
  参考文献：
  名称：

  Sulfamoyl-4-oxoquinoline-3-carboxamides: Novel potentiators of defective ΔF508-cystic fibrosis transmembrane conductance regulator chloride channel gating

  摘要：

  The synthesis of a small collection of sulfamoyl-4-oxoquinoline-3-carboxamides is described for use as correctors of defective gating of the Delta F508-cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. Several compounds with submicromolar potency were obtained. N-Ethyl 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (7b) was found to be the most effective sulfonamide corrector of defective Delta F508-CFTR gating. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.050
• 作为试剂：
  描述：

  (2R,3S)-1-(tert-butyloxycarbonyl)-3-hydroxy-2-phenylpiperidine 在 (2-methoxybenzyl)(2-nitrobenzenesulfonyl)amine 、 吡啶 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 6-phenyl-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  小号Ñ 2 2-取代的3-哌啶醇甲磺酸酯与结构的保留的反应：应用到（2的不对称合成- [R，3小号）-CP-99,994

  摘要：

  从受保护的（S）-3-羟基戊二酰亚胺2a开始，实现了（2 R，3 S）-CP-99,994 8的不对称合成。关键步骤是导致邻吡咯烷基-叠氮鎓中间体25和随后的区域选择性开环反应的邻近基团参与。在不涉及邻组参与的情况下，仅获得淘汰产品15。

  DOI：

  10.1016/j.tetasy.2006.12.009

文献信息

• Sulfamoyl-4-oxoquinoline-3-carboxamides: Novel potentiators of defective ΔF508-cystic fibrosis transmembrane conductance regulator chloride channel gating
  作者：Yat Fan Suen、Lori Robins、Baoxue Yang、A.S. Verkman、Michael H. Nantz、Mark J. Kurth

  DOI：10.1016/j.bmcl.2005.10.050

  日期：2006.2

  The synthesis of a small collection of sulfamoyl-4-oxoquinoline-3-carboxamides is described for use as correctors of defective gating of the Delta F508-cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. Several compounds with submicromolar potency were obtained. N-Ethyl 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (7b) was found to be the most effective sulfonamide corrector of defective Delta F508-CFTR gating. (c) 2005 Elsevier Ltd. All rights reserved.
• SN2 reaction of 2-substituted 3-piperidinol mesylate with retention of configuration: application to the asymmetric synthesis of (2R,3S)-CP-99,994
  作者：Liang-Xian Liu、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2006.12.009

  日期：2006.12

  Starting from protected (S)-3-hydroxyglutarimide 2a, the asymmetric synthesis of (2R,3S)-CP-99,994 8 was achieved. The crucial steps were a neighboring group participation leading to pyrrolidino-aziridinium intermediate 25 and the subsequent regioselective ring-opening reaction. In the case where neighboring group participation was not involved, only the eliminated product 15 was obtained.

  从受保护的（S）-3-羟基戊二酰亚胺2a开始，实现了（2 R，3 S）-CP-99,994 8的不对称合成。关键步骤是导致邻吡咯烷基-叠氮鎓中间体25和随后的区域选择性开环反应的邻近基团参与。在不涉及邻组参与的情况下，仅获得淘汰产品15。