N-benzyl-N-methyl-4-nitrobenzenesulfonamide | 330978-95-5

• 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-benzyl-N-methyl-4-nitrobenzenesulfonamide
• CAS: 330978-95-5
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: LVCHFWNSSFJLTB-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  481.6±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-4-nitrobenzenesulfonamide 在 potassium carbonate 、 巯基乙酸 作用下， 以 甲醇 为溶剂， 以98%的产率得到N-甲基苄胺
  参考文献：
  名称：

  Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor

  摘要：

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

  DOI：

  10.1021/ol4031606
• 作为产物：
  描述：

  N-甲基苄胺 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到N-benzyl-N-methyl-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor

  摘要：

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.

  DOI：

  10.1021/ol4031606

文献信息

• A cautionary note on the use of p-nitrobenzenesulfonamides as protecting groups
  作者：Peter G.M. Wuts、Jill M. Northuis

  DOI：10.1016/s0040-4039(98)00684-4

  日期：1998.6

  regioselectivity. Cleavage requires addition of thiolate at the sulfonamide carbon, but some addition occurs at the nitro carbon resulting in simple displacement of the nitro group rather than sulfonamide cleavage. The side reaction is most prevalent with cyclic amines and steric effects play only a limited role. This lack of regioselectivity is not observed for o-nitrobenzenesulfonamides.

  发现使用硫醇盐裂解对硝基苯磺酰胺的区域选择性差。裂解需要在磺酰胺碳上添加硫醇盐，但是在硝基碳上发生一些加成，导致硝基的简单置换而不是磺酰胺裂解。副反应在环胺中最为普遍，且空间效应仅发挥有限的作用。对于邻硝基苯磺酰胺没有观察到区域选择性的缺乏。
• Oxidative Debenzylation of <i>N</i>-Benzyl Amides and <i>O</i>-Benzyl Ethers Using Alkali Metal Bromide
  作者：Katsuhiko Moriyama、Yu Nakamura、Hideo Togo

  DOI：10.1021/ol501703y

  日期：2014.7.18

  The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.
• Practical and Cost-Effective Manufacturing Route for the Synthesis of a β-Lactamase Inhibitor
  作者：Steven P. Miller、Yong-Li Zhong、Zhijian Liu、Michael Simeone、Nobuyoshi Yasuda、John Limanto、Zheng Chen、Joseph Lynch、Vincent Capodanno

  DOI：10.1021/ol4031606

  日期：2014.1.3

  Compound 1, a potent and irreversible inhibitor of beta-lactamases, is in clinical trials with beta-lactam antibiotics for the treatment of serious and antibiotic-resistant bacterial infections. A short, scalable, and cost-effective route for the production of this densely functionalized polycyclic molecule is described.