tert-butyl 4-(4-nitro-benzoylamino)benzoate | 1255217-85-6

• 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: tert-butyl 4-(4-nitro-benzoylamino)benzoate
• 英文别名: tert-butyl 4-(4-nitrobenzamido)benzoate
• CAS: 1255217-85-6
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: LRTUVBWNIRRSQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-nitro-benzoylamino)benzoate 在 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 苯胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.08h， 生成 4-(4-(4-((2S,3R)-4-amino-3-methoxy-2-(4-(4-nitrobenzamido)benzamido)-4-oxobutanamido)benzamido)-2-hydroxy-3-isopropoxybenzamido)benzoic acid
  参考文献：
  名称：

  Scalable Syntheses of Methoxyaspartate and Preparation of the Antibiotic Cystobactamid 861-2 and Highly Potent Derivatives

  摘要：

  An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861-2, whose antibacterial properties are determined and compared. The cyano derivative of cystobactamide 861-2 shows superior antibacterial activity against Gram-negative bacteria to any natural cystobactamide tested so far.

  DOI：

  10.1021/acs.orglett.9b03143
• 作为产物：
  描述：

  4-氨基苯甲酸叔丁酯 、 4-硝基苯甲酰氯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以80%的产率得到tert-butyl 4-(4-nitro-benzoylamino)benzoate
  参考文献：
  名称：

  Scalable Syntheses of Methoxyaspartate and Preparation of the Antibiotic Cystobactamid 861-2 and Highly Potent Derivatives

  摘要：

  An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861-2, whose antibacterial properties are determined and compared. The cyano derivative of cystobactamide 861-2 shows superior antibacterial activity against Gram-negative bacteria to any natural cystobactamide tested so far.

  DOI：

  10.1021/acs.orglett.9b03143

文献信息

• Conformational studies of tertiary oligo-m-benzanilides and oligo-p-benzanilides in solution
  作者：Laurent Chabaud、Jonathan Clayden、Madeleine Helliwell、Abigail Page、James Raftery、Lluís Vallverdú

  DOI：10.1016/j.tet.2010.06.037

  日期：2010.8

  A series of oligo-m- and p-benzanilides were made and their conformations in solution were studied by NMR. In most cases, conformational mixtures were observed as soon as three or more monomers were incorporated into the oligomer. Some crystal structures were obtained, which indicated that helical conformations were adopted in the solid state. (C) 2010 Elsevier Ltd. All rights reserved.