11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine | 199486-38-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine
• 英文别名: (11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide；(11R,14S)-N-[(3-fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.13,7]henicosa-1(18),3,5,7(21),16,19-hexaene-14-carboxamide
• CAS: 199486-38-9
• 化学式: C₃₂H₂₇FN₄O₇
• 分子量: 598.587
• InChiKey: WNMODHTWYADFER-BHBYDHKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine 在 18-冠醚-6 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到(1S,16R)-23-nitro-7,21-dioxa-15,28,30-triazahexacyclo[14.13.2.23,6.217,20.18,12.122,26]heptatriaconta-3(37),4,6(36),8,10,12(35),17(34),18,20(33),22,24,26(32)-dodecaene-14,29,31-trione
  参考文献：
  名称：

  Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin

  摘要：

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00171-4
• 作为产物：
  描述：

  (RS)-N-trifluoroacetyl-4-fluoro-3-nitrophenylalanine methyl ester 在 palladium on activated charcoal lithium hydroxide 、 氯化亚砜 、 亚硝酸特丁酯 、 18-crown-ether 、 protease type VIII-A from Bacillus licheniformis 、 氢气 、 1-羟基苯并三唑 、 potassium hydrogencarbonate 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine
  参考文献：
  名称：

  The first synthesis of 16+15-membered bicyclic polypeptide model of A-O-C-B-O-D rings of kistamicin

  摘要：

  A 16+15 membered bicyclic polypeptide containing biaryl ether bonds, model of A-O-C-B-O-D rings of kistamicin has been synthesized by sequential intramolecular SNAr reactions. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10217-9

文献信息

• Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin
  作者：René Beugelmans、Georges Roussi、Eduardo González Zamora、Annie-Claude Carbonnelle

  DOI：10.1016/s0040-4020(99)00171-4

  日期：1999.4

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.
• The first synthesis of 16+15-membered bicyclic polypeptide model of A-O-C-B-O-D rings of kistamicin
  作者：René Beugelmans、Eduardo González Zamora、Georges Roussi

  DOI：10.1016/s0040-4039(97)10217-9

  日期：1997.11

  A 16+15 membered bicyclic polypeptide containing biaryl ether bonds, model of A-O-C-B-O-D rings of kistamicin has been synthesized by sequential intramolecular SNAr reactions. (C) 1997 Published by Elsevier Science Ltd.