(2S)-1-(p-nitrophenyl)-2-phthalimido-2-propen-1-one | 63457-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S)-1-(p-nitrophenyl)-2-phthalimido-2-propen-1-one
• 英文别名: 2-[3-(4-Nitrophenyl)-3-oxoprop-1-en-2-yl]-1H-isoindole-1,3(2H)-dione；2-[3-(4-nitrophenyl)-3-oxoprop-1-en-2-yl]isoindole-1,3-dione
• CAS: 63457-11-4
• 化学式: C₁₇H₁₀N₂O₅
• 分子量: 322.277
• InChiKey: PNGRNZQABTVHDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1-(p-nitrophenyl)-2-phthalimido-2-propen-1-one 在 potassium permanganate 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 以0.11 g的产率得到1-(p-nitrophenyl)-2,3-di(phthalimido)-propanone
  参考文献：
  名称：

  2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones

  摘要：

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00483-3
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 在 2,4,6-三甲基吡啶 、 jones reagent 、 三乙胺 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (2S)-1-(p-nitrophenyl)-2-phthalimido-2-propen-1-one
  参考文献：
  名称：

  2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones

  摘要：

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00483-3

文献信息

• Derivatives of Ribosome-Inhibiting Antibiotic Chloramphenicol Inhibit the Biosynthesis of Bacterial Cell Wall
  作者：Sivan Louzoun Zada、Keith D. Green、Sanjib K. Shrestha、Ido M. Herzog、Sylvie Garneau-Tsodikova、Micha Fridman

  DOI：10.1021/acsinfecdis.8b00078

  日期：2018.7.13

  evidence and metabolic labeling of a cell wall peptidoglycan suggested that compounds 1 and 4 caused extensive damage to the envelope of Staphylococcus aureus cells by inhibition of the early stage of cell wall peptidoglycan biosynthesis. Unlike the effect of membrane-disrupting antimicrobial cationic amphiphiles, these compounds did not rapidly permeabilize the bacterial membrane. Like the parent antibiotic

  在这里，我们描述了细菌翻译抑制抗生素氯霉素（CAM）的α，β-不饱和羰基衍生物的制备和评价。与母体抗生素相比，两种含有α，β-不饱和酮的化合物（1和4）对一组革兰氏阳性病原体表现出更广谱的活性，其最低抑菌浓度范围为2–32μg/ mL。有趣的是，与母体CAM不同，这些化合物不会抑制细菌的翻译。显微镜证据和细胞壁肽聚糖的代谢标记表明化合物1和4对金黄色葡萄球菌的包膜造成了广泛破坏通过抑制细胞壁肽聚糖生物合成的早期来抑制细胞的生长。与破坏膜的阳离子阳离子两亲物的作用不同，这些化合物不能迅速渗透细菌膜。像母体抗生素CAM一样，化合物1和4对金黄色葡萄球菌具有抑菌作用。化合物1和4对永生化的有核哺乳动物细胞都具有细胞毒性。但是，它们都没有对哺乳动物的红细胞造成可测量的膜损伤。这些数据表明，所报道的源自CAM的抗微生物剂为开发新型细菌细胞壁生物合成抑制性抗生素提供了新的分子支架。
• 2-Amino-1-phenyl-propan-1,3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones
  作者：Tamas E Gunda、Ferenc Sztaricskai

  DOI：10.1016/s0040-4020(97)00483-3

  日期：1997.6

  3,4-cis-1-N-(1'-phenyl-1',3'-dihydroxy-2'-propyl)-3 -phthalimido-4-styrylazetidinones were obtained in optically pure form by chiral Staudinger reaction. The cis-alpha/beta-ratio could be influenced by: the protective groups of the diol moiety. Removal of the chiral auxiliarity could be accomplished by direct oxidation, or by previous double bond formation, thus the 2-amino-1-phenyl-propan-1,3-diol can be regarded to a generally useful chiral auxiliary. (C) 1997 Elsevier Science Ltd.