N-methyl-2-[(4-nitrophenyl)sulfonylamino]acetamide | 1448453-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-2-[(4-nitrophenyl)sulfonylamino]acetamide
• CAS: 1448453-30-2
• 化学式: C₉H₁₁N₃O₅S
• 分子量: 273.269
• InChiKey: JREJFZGRVPZWLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methyl-2-[(4-nitrophenyl)sulfonylamino]acetamide 在 水 、 六甲基二硅氮烷 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N,N'-((1,1,3,3-tetramethyldisiloxane-1,3-diyl)bis(methylene))bis(N-methyl-2-((4-nitrophenyl)sulfonamido)acetamide)
  参考文献：
  名称：

  1-Organosulfonyl-2-sila-5-piperazinones: Synthesis, molecular and crystal structure, and chemical transformations into 2-aminoacid derivatives

  摘要：

  The reaction of chloro(chloromethyl)dimethylsilane and hexamethyldisilazane with N-methylamides of N'-organosulfonyl-2-amino acids (1a-e), the derivatives of N-mesylglycine (a), N-tosylglycine (b), N-nosylglycine (c), N-nosylalanine (d) and N-nosylleucine (e), affords new type of silacyclanes, 1-organosulfonyl-2-sila-5-piperazinones 2a-e. The presence of very labile Si-N bonds in compounds 2 can be utilised in a variety of synthetic applications. The hydrolysis of 2a-e yields disiloxanes 3a-e, which can be subsequently transformed into fluorosilanes, such as 4a, by the reaction with boron trifluoride. Ring-opening reactions of piperazinones 2b with 1-chloromethyl-2-pyrrolidone and acetyl bromide lead to previously unknown silyloxonium chloride 6b and silyloxonium bromide 8b, respectively, containing fragments of 2-amino acids as C,O-chelate ligands.Crystal structures of N-methylamide 1b, piperazinones 2a, d, e, disiloxanes 3c, e, fluorosilane 4a, silyloxonium chloride 6b and silyloxonium bromide 8b have been determined by X-ray diffraction study. The silicon atom in piperazinones and disiloxanes is tetracoordinated while compounds 4a, 6b and 8b contain pentacoordinated Si atoms. Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.05.044
• 作为产物：
  描述：

  N-[(4-硝基苯基)磺酰基]甘氨酸 在 氯化亚砜 作用下， 以 正己烷 、 水 为溶剂， 反应 124.0h， 生成 N-methyl-2-[(4-nitrophenyl)sulfonylamino]acetamide
  参考文献：
  名称：

  1-Organosulfonyl-2-sila-5-piperazinones: Synthesis, molecular and crystal structure, and chemical transformations into 2-aminoacid derivatives

  摘要：

  The reaction of chloro(chloromethyl)dimethylsilane and hexamethyldisilazane with N-methylamides of N'-organosulfonyl-2-amino acids (1a-e), the derivatives of N-mesylglycine (a), N-tosylglycine (b), N-nosylglycine (c), N-nosylalanine (d) and N-nosylleucine (e), affords new type of silacyclanes, 1-organosulfonyl-2-sila-5-piperazinones 2a-e. The presence of very labile Si-N bonds in compounds 2 can be utilised in a variety of synthetic applications. The hydrolysis of 2a-e yields disiloxanes 3a-e, which can be subsequently transformed into fluorosilanes, such as 4a, by the reaction with boron trifluoride. Ring-opening reactions of piperazinones 2b with 1-chloromethyl-2-pyrrolidone and acetyl bromide lead to previously unknown silyloxonium chloride 6b and silyloxonium bromide 8b, respectively, containing fragments of 2-amino acids as C,O-chelate ligands.Crystal structures of N-methylamide 1b, piperazinones 2a, d, e, disiloxanes 3c, e, fluorosilane 4a, silyloxonium chloride 6b and silyloxonium bromide 8b have been determined by X-ray diffraction study. The silicon atom in piperazinones and disiloxanes is tetracoordinated while compounds 4a, 6b and 8b contain pentacoordinated Si atoms. Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.05.044

文献信息

• 1-Organosulfonyl-2-sila-5-piperazinones: Synthesis, molecular and crystal structure, and chemical transformations into 2-aminoacid derivatives
  作者：Alexandr G. Shipov、Eugenia P. Kramarova、Huntse Fang、Dmitry E. Arkhipov、Alexey A. Nikolin、Sergey Yu. Bylikin、Vadim V. Negrebetsky、Alexandr A. Korlyukov、Natalia A. Voronina、Alan R. Bassindale、Peter G. Taylor、Yuri I. Baukov

  DOI：10.1016/j.jorganchem.2013.05.044

  日期：2013.10

  The reaction of chloro(chloromethyl)dimethylsilane and hexamethyldisilazane with N-methylamides of N'-organosulfonyl-2-amino acids (1a-e), the derivatives of N-mesylglycine (a), N-tosylglycine (b), N-nosylglycine (c), N-nosylalanine (d) and N-nosylleucine (e), affords new type of silacyclanes, 1-organosulfonyl-2-sila-5-piperazinones 2a-e. The presence of very labile Si-N bonds in compounds 2 can be utilised in a variety of synthetic applications. The hydrolysis of 2a-e yields disiloxanes 3a-e, which can be subsequently transformed into fluorosilanes, such as 4a, by the reaction with boron trifluoride. Ring-opening reactions of piperazinones 2b with 1-chloromethyl-2-pyrrolidone and acetyl bromide lead to previously unknown silyloxonium chloride 6b and silyloxonium bromide 8b, respectively, containing fragments of 2-amino acids as C,O-chelate ligands.Crystal structures of N-methylamide 1b, piperazinones 2a, d, e, disiloxanes 3c, e, fluorosilane 4a, silyloxonium chloride 6b and silyloxonium bromide 8b have been determined by X-ray diffraction study. The silicon atom in piperazinones and disiloxanes is tetracoordinated while compounds 4a, 6b and 8b contain pentacoordinated Si atoms. Crown Copyright (C) 2013 Published by Elsevier B.V. All rights reserved.