3,11-Bis-(2-nitro-benzenesulfonyl)-4-oxa-3,8,11,17-tetraaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-8-carboxylic acid tert-butyl ester | 182576-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,11-Bis-(2-nitro-benzenesulfonyl)-4-oxa-3,8,11,17-tetraaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-8-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3,11-bis[(2-nitrophenyl)sulfonyl]-4-oxa-3,8,11,17-tetrazabicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-8-carboxylate
• CAS: 182576-32-5
• 化学式: C₂₉H₃₄N₆O₁₁S₂
• 分子量: 706.755
• InChiKey: JFADQQAKUJEVEP-UHFFFAOYSA-N

物化性质

• 沸点：
  836.0±75.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,11-Bis-(2-nitro-benzenesulfonyl)-4-oxa-3,8,11,17-tetraaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-8-carboxylic acid tert-butyl ester 在 sodium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以97%的产率得到8-(tert-butoxycarbonyl)-4-oxa-3,8,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene
  参考文献：
  名称：

  溶液相组合化学I.聚氮杂环烷骨架和叔胺文库的合成

  摘要：

  通过一种新的环化方法，然后进行选择性脱保护，可以高产率高效地合成了三种新型的非对称多氮杂氮杂环庚烷骨架1-3。通过溶液相的同时添加功能来组合支架2，以提供16个纯叔胺库（总共1600种化合物）。

  DOI：

  10.1016/0040-4039(96)01627-9
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3,11-Bis-(2-nitro-benzenesulfonyl)-4-oxa-3,8,11,17-tetraaza-bicyclo[11.3.1]heptadeca-1(16),13(17),14-triene-8-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  溶液相组合化学I.聚氮杂环烷骨架和叔胺文库的合成

  摘要：

  通过一种新的环化方法，然后进行选择性脱保护，可以高产率高效地合成了三种新型的非对称多氮杂氮杂环庚烷骨架1-3。通过溶液相的同时添加功能来组合支架2，以提供16个纯叔胺库（总共1600种化合物）。

  DOI：

  10.1016/0040-4039(96)01627-9

文献信息

• Solution Phase Combinatorial Chemistry. Discovery of Novel Polyazapyridinophanes with Potent Antibacterial Activity by a Solution Phase Simultaneous Addition of Functionalities Approach
  作者：Haoyun An、Lendell L. Cummins、Richard H. Griffey、Ramesh Bharadwaj、Becky D. Haly、Allister S. Fraser、Laura Wilson-Lingardo、Lisa M. Risen、Jacqueline R. Wyatt、P. Dan Cook

  DOI：10.1021/ja964153r

  日期：1997.4.1

  Chemical modification of pre-formed asymmetric polyazaphane scaffolds by simultaneous addition of Functionality (letters) in solution has been developed for the preparation of tertiary nitrogen-based combinatorial chemistry libraries. This approach has some significant advantages over the more commonly employed solid phase bead splitting/resction/mixing procedures for the preparation of libraries. Three novel, asymmetric polyazaphanes 32, 33, and 37 have been synthesized in high yields by an efficient cyclization of 2,6-bis(bronzomethyl)pyridine (31) with new orthogonally protected triamines 29, 30, and 35, respectively. Selective deprotection of 32, 33, and 37 provided mono-t-Boc-protected scaffolds 1-3 suitable for solution phase, simultaneous addition of functionalities. Model studies of small libraries of scaffold 2 using CZE analyses indicated that simultaneous addition of 10 benzylic bromide alkylating functionalities would result in libraries containing approximately equimolar amounts of all possible compounds. Sixteen purified tertiary amine libraries 4-19 (total complexity of 1600 compounds) were generated by this procedure from scaffold 2. A ''fix-last'' combinatorial method was devised to minimize chemical reactions. Several first-round sublibraries of scaffold 2, containing a mixture of 100 compounds, exhibited potent antimicrobial activities. Twenty single compounds 63-82 with uniform functionalities at the combinatorialized sites were synthesized. Some of these pure compounds were more active, while others were less active, compared with the parent mixtures 5 and 10.