N-(4-nitrophenylsulfonyl)glycinoyl chloride | 106148-57-6

• 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-(4-nitrophenylsulfonyl)glycinoyl chloride
• 英文别名: N-(4-nitrophenylsulfonyl)glycine acid chloride；2-[(4-Nitrophenyl)sulfonylamino]acetyl chloride
• CAS: 106148-57-6
• 化学式: C₈H₇ClN₂O₅S
• 分子量: 278.673
• InChiKey: NBNRVZCXNRJVEE-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±55.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenylsulfonyl)glycinoyl chloride 在 水 、 六甲基二硅氮烷 作用下， 以 乙醇 、 正己烷 、 水 为溶剂， 反应 144.0h， 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 五氯化磷 作用下， 以 乙酸乙酯 为溶剂， 以70%的产率得到N-(4-nitrophenylsulfonyl)glycinoyl chloride
  参考文献：
  名称：

  R22(8) 氢键二聚体基序的模拟物：合成及对磺胺噻唑和磺胺吡啶结晶的影响

  摘要：

  双 [4-(羟基氨基) 苯基磺酰基] 哌嗪 5、二酮哌嗪 10 和苯 14 被合成为 R2/2(8) 母题的模拟物，它出现在磺胺噻唑的一种晶体多晶型和磺胺吡啶的几种多晶型中。当存在于磺胺噻唑和磺胺吡啶的结晶中时，发现这些模拟物在有利于形成不含 R2/2(8) 基序的多晶型物的结晶条件下几乎没有影响。然而，发现模拟物在磺胺噻唑从 1-丙醇结晶中完全或部分抑制了形式 I 磺胺噻唑的形成，其中含有 R2/2(8) 二聚体。在磺胺吡啶的结晶中，发现模拟物促进了不包含 R2/2(8) 基序的 III 型的形成。因此，这些化合物似乎是“量身定制的”

  DOI：

  10.1002/ejoc.200901042

文献信息

• New lactam-containing benzenesulfonamides: design, synthesis, and in silico and in vitro studies
  作者：A. D. Shagina、E. P. Kramarova、D. V. Tarasenko、D. I. Gonchar、D. N. Lyakhman、A. A. Lagunin、K. A. Sobyanin、T. A. Shmigol’、Yu. I. Baukov、Vad. V. Negrebetsky

  DOI：10.1007/s11172-021-3112-8

  日期：2021.3

  spectroscopy, NMR spectroscopy, and elemental analysis data. According to the results of studies in vitro, compounds 1a–d and 2a–d efficiently suppress the growth of S. aureus. Lactam-containing benzenesulfonamides bearing the bromine atom or methyl or nitro group at position 4 manifested the most pronounced activity.

  使用结构活性计算机模型（网络服务PASS Online，AntiBac-Pred和GUSAR急性毒性）设计和分析了一组新的含芳基磺酰基甘氨酸1a-d和2a-d的内酰胺的衍生物。对于这些衍生物，预测了其对金黄色葡萄球菌的抗菌活性以及低毒性。化合物1a-d和2a-d是通过N-三甲基甲硅烷基内酰胺与4-取代的[（苯基）磺酰基]氨基乙酰氯的反应合成的。通过IR光谱，NMR光谱和元素分析数据确认了新化合物的结构。根据体外研究结果，化合物1a–d和2a–d有效抑制金黄色葡萄球菌的生长。在位置4处带有溴原子或甲基或硝基的含内酰胺的苯磺酰胺表现出最明显的活性。
• Sipyagin, A. M.; Kartsev, V. G., Journal of Organic Chemistry USSR (English Translation), 1986, p. 353 - 361
  作者：Sipyagin, A. M.、Kartsev, V. G.

  DOI：——

  日期：——
• SIPYAGIN, A. M.;KARTSEV, V. G., ZH. ORGAN. XIMII, 1986, 22, N 2, 401-409
  作者：SIPYAGIN, A. M.、KARTSEV, V. G.

  DOI：——

  日期：——
• 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.
• Mimics of a R22(8) Hydrogen-Bond Dimer Motif: Synthesis and Influence on the Crystallisation of Sulfathiazole and Sulfapyridine
  作者：Simon E. Lawrence、Marie T. McAuliffe、Humphrey A. Moynihan

  DOI：10.1002/ejoc.200901042

  日期：2010.2

  synthesised as mimics of an R2/2(8) motif, which occurs in one crystal polymorph of sulfathiazole and in several polymorphs of sulfapyridine. When present in crystallisations of sulfathiazole and sulfapyridine, these mimics were found to have little or no effect under crystallisation conditions that favour the formation of polymorphs not containing R2/2(8) motifs. However, the mimics were found to completely

  双 [4-(羟基氨基) 苯基磺酰基] 哌嗪 5、二酮哌嗪 10 和苯 14 被合成为 R2/2(8) 母题的模拟物，它出现在磺胺噻唑的一种晶体多晶型和磺胺吡啶的几种多晶型中。当存在于磺胺噻唑和磺胺吡啶的结晶中时，发现这些模拟物在有利于形成不含 R2/2(8) 基序的多晶型物的结晶条件下几乎没有影响。然而，发现模拟物在磺胺噻唑从 1-丙醇结晶中完全或部分抑制了形式 I 磺胺噻唑的形成，其中含有 R2/2(8) 二聚体。在磺胺吡啶的结晶中，发现模拟物促进了不包含 R2/2(8) 基序的 III 型的形成。因此，这些化合物似乎是“量身定制的”