(11S)-10,13-Dioxo-2-oxa-18-amino-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene | 160877-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (11S)-10,13-Dioxo-2-oxa-18-amino-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene
• 英文别名: (11S)-18-amino-11-methyl-2-oxa-9,12-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-10,13-dione
• CAS: 160877-46-3
• 化学式: C₁₉H₂₁N₃O₃
• 分子量: 339.394
• InChiKey: ORZXIHMUXCIJJU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11S)-10,13-Dioxo-2-oxa-18-amino-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene 在 亚硝酸特丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 (11S)-10,13-Dioxo-2-oxa-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene 、 (11R)-10,13-Dioxo-2-oxa-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene
  参考文献：
  名称：

  SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models

  摘要：

  The first examples of macrocyclization using the intramolecular SNAr reaction are reported. The method has allowed the efficient preparation of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compound 20 was submitted to the same macrocyclization conditions, two atropisomers 21 and 22 were isolated and characterized.

  DOI：

  10.1021/jo00098a010
• 作为产物：
  描述：

  4-氟-3-硝基苄醇 在 盐酸 、 水 、 三溴化磷 、 铁粉 、 sodium hydride 、 potassium carbonate 、 iron(II) sulfate 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.08h， 生成 (11S)-10,13-Dioxo-2-oxa-18-amino-11-methyl-9,12-diazatricyclo<14.2.2.1^3,7>heneicosa-3,5,7(21),16,18,19-hexaene
  参考文献：
  名称：

  SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models

  摘要：

  The first examples of macrocyclization using the intramolecular SNAr reaction are reported. The method has allowed the efficient preparation of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compound 20 was submitted to the same macrocyclization conditions, two atropisomers 21 and 22 were isolated and characterized.

  DOI：

  10.1021/jo00098a010

文献信息

• SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models
  作者：Rene Beugelmans、Girij Pal Singh、Michele Bois-Choussy、Jacqueline Chastanet、Jieping Zhu

  DOI：10.1021/jo00098a010

  日期：1994.9

  The first examples of macrocyclization using the intramolecular SNAr reaction are reported. The method has allowed the efficient preparation of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compound 20 was submitted to the same macrocyclization conditions, two atropisomers 21 and 22 were isolated and characterized.