2-bromo-N-[(4-methylphenyl)sulfonyl]acetylamide | 156878-95-4

• 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: 2-bromo-N-[(4-methylphenyl)sulfonyl]acetylamide
• 英文别名: 2-bromo-N-[(tosyl)sulfonyl]acetamide；2-bromo-N-tosylethanamide；2-bromo-N-tosylacetamide；2-bromo-N-(4-methylphenyl)sulfonylacetamide
• CAS: 156878-95-4
• 化学式: C₉H₁₀BrNO₃S
• 分子量: 292.153
• InChiKey: CADLGHOSMGRYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-[(4-methylphenyl)sulfonyl]acetylamide 在 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 10-{2-{[(4-methylphenyl)sulfonyl]amino}-2-oxoethyl}-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid
  参考文献：
  名称：

  ta衍生的N-磺酰基乙酰胺（H 4（dota-NHSO 2 R）= 10- {2-[（R）磺酰基氨基] -2-氧乙基} -1,4,7,10-四氮杂环十二烷- 1,4,7-三乙酸）：用于磁共振成像应用的新型松弛剂

  摘要：

  合成了基于H 3 do3a（= 1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸）结构并带有一个N-磺酰基乙酰胺臂的四个镧系离子的新配体，即H 4 dota- NHSO 2 R = 10- {2-[（R）磺酰基氨基] -2-氧代乙基} -1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸1a – e。对一个这样的配体的15 N标记的Eu 3+配合物1d的15 N-NMR研究表明，N-磺酰基乙酰胺臂的配位涉及羰基O原子而不是N原子。相应Gd的弛豫特性研究了3+配合物随pH和温度的变化。这些配合物在20 MHz和25°时具有4.5–5.3 mM -1 s -1范围内的弛豫度，其特征是在其内部配位域中存在单个H 2 O分子。与其他阴离子络合物相比，该分子的平均停留寿命相对较长（500-700 ns）。H 2 O交换的缓慢速度可以通过N-磺酰基乙酰胺臂上负电荷的广泛离域来证明。配位的H 2

  DOI：

  10.1002/hlca.200590041
• 作为产物：
  描述：

  2-溴乙酰胺 、 对甲苯磺酰氯 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到2-bromo-N-[(4-methylphenyl)sulfonyl]acetylamide
  参考文献：
  名称：

  Synthesis, antimicrobial activity and quantum calculations of Novel sulphonamide derivatives

  摘要：

  THE reactivity of 2-bromo-N-(phenylsulfonyl) acetamide derivatives 3a-c towards some nitrogen-based nucleophiles was studied in this investigation and gave the corresponding aminothiazole 6a-c, aminooxazole 7a-c, quinazoline-2-yl 10a-c; respectively. Furthermore, the reaction of acetamide derivatives 3a-c with aminopyridine gave pyridine-4-ylamino 12a-c. Reaction of acetamide derivatives 3a-c with benzo-2-thiol derivatives afforded benzo [d]thiazol-2-ylthio 14a-c and 1H-benzo[d]imidazol-2-yl) thio derivatives 16a-c; respectively. The synthesized compounds displayed good antimicrobial activity. Additionally, compounds 12a and 14a exhibited high activity towards most of the strains. The computational calculations for 12a and 14a were carried out via HF/6-31G(d) and DFT B3LYP/6-31G(d) basis sets and the corresponding results of HOMO-LUMO energy gap and Mulliken atomic charges were tabulated. This correlation between experimental and theoretical calculations provided a good confirmation for anticipated new compounds.

  DOI：

  10.21608/ejchem.2019.6870.1575

文献信息

• Synthesis of N-(tosyl)azetidin-2-imines
  作者：A Van Camp、D Goossens、M Moya-Portuguez、J Marchand-Brynaert、L Ghosez

  DOI：10.1016/s0040-4039(00)77413-2

  日期：1980.1

  A synthetic route for N-(tosyl)azetidin-2-imines 6, a novel class of derivatives of β-lactams, has been developed. The procedure is applicable to the synthesis of azetidin-2-imines related to penicillins and cephalosporins.

  已经开发出N-（甲苯磺酰基）氮杂环丁烷-2-亚胺6的合成路线，这是一类新型的β-内酰胺衍生物。该方法适用于与青霉素和头孢菌素有关的氮杂环丁烷-2-亚胺的合成。
• Coupling of α-bromoamides and unactivated alkenes to form γ-lactams through EDA and photocatalysis
  作者：Sean M. Treacy、Daniel R. Vaz、Syed Noman、Cédric Tard、Tomislav Rovis

  DOI：10.1039/d2sc05973h

  日期：——

  methods for the synthesis of this valuable motif, previous redox approaches to γ-lactam synthesis from α-haloamides and olefins require additional electron withdrawing functionality as well as N-aryl substitution to promote electrophilicity of the intermediate radical and prevent competitive O-nucleophilicity about the amide. Using α-bromo imides and α-olefins, our strategy enables the synthesis of monosubstituted

  γ-内酰胺在小分子药物中很普遍，并为高度取代的吡咯烷提供有用的前体。尽管有许多方法可以合成这一有价值的基序，但以前从 α- 卤代酰胺和烯烃合成 γ-内酰胺的氧化还原方法需要额外的吸电子功能以及N-芳基取代以促进中间基团的亲电性并防止关于酰胺的竞争性O-亲核性。使用 α-溴酰亚胺和 α-烯烃，我们的策略能够以正式的 [3 + 2] 方式合成单取代保护的 γ-内酰胺。这些物种准备进一步衍生成更复杂的杂环支架，以补充现有方法。C-Br 键断裂通过两种互补的方法发生，在溴酰亚胺和含氮碱基之间形成电子供体-受体复合物，该复合物经历光诱导电子转移，或用光催化剂进行三重态敏化，以提供亲电碳中心自由基。路易斯酸的加入允许进一步增加中间体碳中心自由基的亲电性，
• Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂
  作者：Rob C. Oslund、Nathan Cermak、Michael H. Gelb

  DOI：10.1021/jm800422v

  日期：2008.8.1

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.
• Synthesis, structure and coordination properties of three cyclam-based ligands bearing one scorpionate arm
  作者：Ramu Kannappan、Yoann Rousselin、Rim Zaari Jabri、Christine Goze、Stéphane Brandès、Roger Guilard、Abdellah Zrineh、Franck Denat

  DOI：10.1016/j.ica.2011.04.013

  日期：2011.7

  In this work, three new cyclam-based ligands L-1, L-2 and L-3 bearing N-sulfonylacetamide pendant arm and their Cu(II), Zn(II), Cd(II) and Pb(II) complexes were synthesized and characterized by mass spectrometry, NMR, infrared and UV-Vis spectroscopies. The ligands present an original zwitterionic form in which the nitrogen atom of the sulfonylacetamide is deprotonated and one nitrogen of the macrocycle is protonated. This observation was confirmed by X-ray crystallography. The infrared spectra of the ligands revealed very low CO vibrational band values which can be explained by the fact that the oxygen atom is involved in some hydrogen bonds. The amidate form of the sulfonylacetamide arm is maintained upon complexation. Infrared data revealed a probable different coordination mode for Pb(II) than for the other three cations. Some additional studies by UV-Vis and EPR spectroscopies were performed for the Cu(II) complexes. Finally, the geometry coordination of the Cu(II) L-3, Zn(II) L-3 and Cd(II) L-3 complexes in the solid state was studied by X-ray crystallography. (C) 2011 Elsevier B. V. All rights reserved.
• CAMP A. VAN; GROSSENS D.; MOYA-PORTUGUEZ M.; MARCHAND-BRYNAERT J.; GHOSEZ+, TETRAHEDRON LETT., 1980, 21, NO 32, 3081-3084
  作者：CAMP A. VAN、 GROSSENS D.、 MOYA-PORTUGUEZ M.、 MARCHAND-BRYNAERT J.、 GHOSEZ+

  DOI：——

  日期：——