7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene | 182576-19-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene
• 英文别名: Tert-butyl 3,7,12,18-tetrazabicyclo[12.3.1]octadeca-1(17),14(18),15-triene-7-carboxylate
• CAS: 182576-19-8
• 化学式: C₁₉H₃₂N₄O₂
• 分子量: 348.489
• InChiKey: SWDFKNZSEMTTLT-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene 在 potassium carbonate 、 三氟乙酸 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 4.0h， 生成 3,12-Bis-(3-bromo-benzyl)-3,7,12,18-tetraaza-bicyclo[12.3.1]octadeca-1(18),14,16-triene
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Discovery of Novel Polyazapyridinophanes with Potent Antibacterial Activity by a Solution Phase Simultaneous Addition of Functionalities Approach

  摘要：

  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.

  DOI：

  10.1021/ja964153r
• 作为产物：
  描述：

  亚精胺 在 ammonium hydroxide 、 水 、 potassium carbonate 、 caesium carbonate 、 苯硫酚 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 47.0h， 生成 7-(tert-butoxycarbonyl)-3,7,12,18-tetraazabicyclo[12.3.1]octadeca-1(18),14,16-triene
  参考文献：
  名称：

  Solution Phase Combinatorial Chemistry. Discovery of Novel Polyazapyridinophanes with Potent Antibacterial Activity by a Solution Phase Simultaneous Addition of Functionalities Approach

  摘要：

  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.

  DOI：

  10.1021/ja964153r

文献信息

• Solution phase combinatorial chemistry I. synthesis of polyazacyclophane scaffolds and tertiary amine libraries
  作者：Haoyun An、P.Dan Cook

  DOI：10.1016/0040-4039(96)01627-9

  日期：1996.9

  Three novel unsymmetrical polyazacyclophane scaffolds 1–3 were efficiently synthesized in high yields by a new cyclization method followed by selective deprotection. Scaffold 2 was combinatorialized by solution phase simultaneous addition of functionalities to provide 16 pure tertiary amine libraries (total 1600 compounds).

  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）。