18-Nitro-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione | 163395-21-9

• 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: 18-Nitro-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione
• CAS: 163395-21-9
• 化学式: C₁₇H₁₅N₃O₅
• 分子量: 341.323
• InChiKey: ULVORXNRMMYYSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  18-Nitro-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione 在 铁粉 、 iron(II) sulfate 作用下， 以 水 为溶剂， 反应 3.0h， 以84%的产率得到18-Amino-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione
  参考文献：
  名称：

  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

  摘要：

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

  DOI：

  10.1021/jo00125a026
• 作为产物：
  描述：

  3-氰基苯酚 在 盐酸 、 甲醇 、 硼烷四氢呋喃络合物 、 氯甲酸乙酯 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 18-Nitro-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-10,13-dione
  参考文献：
  名称：

  14元大环的新途径：替考拉宁模型FOG环的合成

  摘要：

  为合成14元大环化合物，开发了一种基于分子内S N Ar反应的新策略。容易进行大环化的原因已经得到了先进的研究，并得到了计算研究的支持。

  DOI：

  10.1016/0040-4039(95)00015-5

文献信息

• A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
  作者：Jieping Zhu、Rene Beugelmans、Sebastien Bourdet、Jacqueline Chastanet、George Roussi

  DOI：10.1021/jo00125a026

  日期：1995.10

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.
• A new access to 14-membered macrocycle: Synthesis of model F-O-G ring of teicoplanin
  作者：René Beugelmans、Sebastien Bourdet、Jieping Zhu

  DOI：10.1016/0040-4039(95)00015-5

  日期：1995.2

  A new strategy based upon the intramolecular SNAr reaction was developped for the synthesis of 14-membered macrocycle. The reason for the easy macrocyclisation was advanced and supported by computational studies.

  为合成14元大环化合物，开发了一种基于分子内S N Ar反应的新策略。容易进行大环化的原因已经得到了先进的研究，并得到了计算研究的支持。