1-(2-硝基苯磺酰基)氨基-4-(叔丁氧羰基)氨基丁烷 | 211512-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-硝基苯磺酰基)氨基-4-(叔丁氧羰基)氨基丁烷
• 英文名称: 1-(2-nitrobenzenesulfonyl)amino-4-(tert-butoxycarbonyl)aminobutane
• 英文别名: N-(4-tert-butoxycarbonylaminobutyl)-o-nitrobenzenesulfonamide；tert-butyl (4-((2-nitrophenyl)sulfonamido)butyl)carbamate；N¹-(2-nitrophenylsulfonyl)-N⁴-(tert-butyloxycarbonyl)-1,4-diaminobutane；tert-butyl N-[4-(2-nitrophenylsulfonamido)butyl]carbamate；N-Nosyl-N'-Boc-1,4-diaminobutane, N-(2-Nitrobenzenesulfonyl)-N'-(t-Butyloxycarbonyl)-1,4-diaminobutane；tert-butyl N-[4-[(2-nitrophenyl)sulfonylamino]butyl]carbamate
• CAS: 211512-15-1
• 化学式: C₁₅H₂₃N₃O₆S
• 分子量: 373.43
• InChiKey: WIYYJAZUNHDNBJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-硝基苯磺酰基)氨基-4-(叔丁氧羰基)氨基丁烷 在 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 N¹,N⁵,N¹⁰-tris(2-nitrobenzenesulfonyl)-1,10-diamino-5-azadecane
  参考文献：
  名称：

  Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries

  摘要：

  Six novel, asymmetric, 19- to 26-membered polyazadipyridinocyclophane scaffolds 1-6 have been synthesized in high yields by an efficient cyclization of ditosylate 39 with the appropriate six fully protected triamines 40-45, followed by removing the 2-nitrobenzenesulfonyl protecting groups. intermediate 39 was synthesized by the Mitsunobu reaction of 2-nitrobenzenesulfonamide (37) with 2,6-pyridinedimethanol (36), and a subsequent tosylation of the resulted diol 38. The fully protected asymmetric triamines 41 and 43 were prepared from the corresponding commercially available triamines 52 and 53. A new synthetic route was developed for the synthesis of the protected asymmetric triamines 44 and 45. Ah reactions were carried out at room temperature in high yields. The reaction of t-Boc-protected scaffold 1, having three reactive sites, with nine benzylic bromides and bromoacetonitrile, using a solution phase simultaneous addition of functionalities combinatorial strategy, Save t-Boc-protected library 7 containing 1000 compounds. Deprotection of library 7 generated the intermediate library 8 with one reactive site. Subsequent reactions at the unsubstituted position of 8 with various functionalities by four types of reactions gave sixteen final libraries 9-24. Libraries 7-24 have different functionalities at the fixed position, and each of them contains 1000 compounds. The reaction of scaffold 2, having four reactive sites without protecting groups, with six sets of polar functionalities afforded eleven diverse libraries 25-35 containing 625 compounds in each library. Totally, twenty-nine libraries containing 24875 compounds were obtained. Eight libraries exhibited antibacterial activity against Escherichia coli imp(-) and Streptococcus pyogenes with the MIC's of 2 to 10-50 mu M. Seven libraries disrupted HIV-1 tat/TAR protein-RNA interactions with IC50's as low as 0.08 mu M. (C) 1998 Elsevier Science Ltd.All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00441-4
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(2-硝基苯磺酰基)氨基-4-(叔丁氧羰基)氨基丁烷
  参考文献：
  名称：

  Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries

  摘要：

  Six novel, asymmetric, 19- to 26-membered polyazadipyridinocyclophane scaffolds 1-6 have been synthesized in high yields by an efficient cyclization of ditosylate 39 with the appropriate six fully protected triamines 40-45, followed by removing the 2-nitrobenzenesulfonyl protecting groups. intermediate 39 was synthesized by the Mitsunobu reaction of 2-nitrobenzenesulfonamide (37) with 2,6-pyridinedimethanol (36), and a subsequent tosylation of the resulted diol 38. The fully protected asymmetric triamines 41 and 43 were prepared from the corresponding commercially available triamines 52 and 53. A new synthetic route was developed for the synthesis of the protected asymmetric triamines 44 and 45. Ah reactions were carried out at room temperature in high yields. The reaction of t-Boc-protected scaffold 1, having three reactive sites, with nine benzylic bromides and bromoacetonitrile, using a solution phase simultaneous addition of functionalities combinatorial strategy, Save t-Boc-protected library 7 containing 1000 compounds. Deprotection of library 7 generated the intermediate library 8 with one reactive site. Subsequent reactions at the unsubstituted position of 8 with various functionalities by four types of reactions gave sixteen final libraries 9-24. Libraries 7-24 have different functionalities at the fixed position, and each of them contains 1000 compounds. The reaction of scaffold 2, having four reactive sites without protecting groups, with six sets of polar functionalities afforded eleven diverse libraries 25-35 containing 625 compounds in each library. Totally, twenty-nine libraries containing 24875 compounds were obtained. Eight libraries exhibited antibacterial activity against Escherichia coli imp(-) and Streptococcus pyogenes with the MIC's of 2 to 10-50 mu M. Seven libraries disrupted HIV-1 tat/TAR protein-RNA interactions with IC50's as low as 0.08 mu M. (C) 1998 Elsevier Science Ltd.All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00441-4

文献信息

• Practical and scalable synthesis of orthogonally protected-2-substituted chiral piperazines
  作者：Srinivas Chamakuri、Manuj M. Shah、David C. H. Yang、Conrad Santini、Damian W. Young

  DOI：10.1039/d0ob01713b

  日期：——

  orthogonally protected, enantiomerically pure 2-substituted piperazines is described. Starting from α-amino acids, within four steps chiral 2-substituted piperazines are obtained. The key transformation involves an aza-Michael addition between an orthogonally bis-protected chiral 1,2-diamine and the in situ generated vinyl diphenyl sulfonium salt derived from 2-bromoethyl-diphenylsulfonium triflate

  描述了一种正交保护的、对映体纯的 2-取代哌嗪的合成路线。从 α-氨基酸开始，在四步内获得手性 2-取代哌嗪。关键的转化涉及正交双保护手性 1,2-二胺和原位生成的由 2-溴乙基-二苯基锍三氟甲磺酸盐衍生的乙烯基二苯基锍盐之间的氮杂迈克尔加成。进行了使用不同保护基团的进一步验证以及多克规模的合成。该方法还应用于手性1,4-二氮杂环己烷和1,4-二氮杂环己烷的构建。此外，该方法用于手性米氮平的正式合成。
• Synthesis of 3-Substituted Bicyclic Imidazo[1,2-<i>d</i>][1,2,4]thiadiazoles and Tricyclic Benzo[4,5]imidazo[1,2-<i>d</i>][1,2,4]thiadiazoles
  作者：Regis Leung-Toung、Tim F. Tam、Yanqing Zhao、Craig D. Simpson、Wanren Li、Denis Desilets、Khashayar Karimian

  DOI：10.1021/jo0507486

  日期：2005.8.1

  cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively

  通过前体[1,2,4] thiadiazol-3-（2 H）one衍生物的交换反应（可能为有用的稠合环[1,2,4]噻二唑支架（例如7a和10b）的通用合成路线）（例如，6和9）与适当取代的腈类（例如溴化氰或p温和的条件下对甲苯磺酰氰化物）进行说明。例如，所述三环3-溴- [1,2,4] THD衍生物（图7a）行小号Ñ氩置换与各种亲核试剂，其中包括胺，丙二酸酯和醇。同样，双环3-对甲苯磺酰基[1,2,4] THD（10b）用作与二胺反应的模板，并且将所得的取代的二胺（例如12a或12e）以线性方式进一步选择性地在N1和/或N2位置衍生化。如方案6所示，获得了3-甲基双环[1,2,4] THD（21）的X射线晶体结构，并确认了通过保护-烷基化-脱保护方案在N1位选择性甲基化。或者，由10b反应短暂聚合N1官能化衍生物还开发了具有适当取代的仲胺的共聚物。因此，有利地利用这些合成策略来获得各种多样化衍生的3-取代的稠环[1
• Preparation of <i>N</i>-Substituted <i>N</i>-Arylsulfonylglycines and Their Use in Peptoid Synthesis
  作者：Steve Jobin、Simon Vézina-Dawod、Claire Herby、Antoine Derson、Eric Biron

  DOI：10.1021/acs.orglett.5b02862

  日期：2015.11.20

  diversity accessible with peptoids and peptide–peptoid hybrids, N-alkylated arylsulfonamides were used to prepare side chain protected N-substituted glycines compatible with solid-phase synthesis. The described procedures give access to peptoid monomers bearing a wide variety of functional groups from commercially available amines in four straightforward steps. The prepared N-substituted N-arylsulfonylglycines

  为了增加类肽和肽-类肽杂化物可利用的化学多样性，N-烷基化的芳基磺酰胺被用于制备与固相合成兼容的侧链保护的N-取代的甘氨酸。所描述的方法可以通过四个简单的步骤从市售胺中获得带有多种官能团的类肽单体。制备的N-取代的N-芳基磺酰基甘氨酸在固相合成中用作单体，以将相关的官能化侧链引入类肽低聚物和肽-类肽杂化物中。
• Practical Synthesis of Spermine, Thermospermine and Norspermine
  作者：Yuka Kariya、Yuta Asanuma、Makoto Inai、Tomohiro Asakawa、Kyoko Ohashi-Ito、Hiroo Fukuda、Masahiro Egi、Toshiyuki Kan

  DOI：10.1248/cpb.c16-00355

  日期：——

  Polyamines, such as spermine (1), thermospermine (2) and norspermine (3), are widely distributed in nature, and have multiple biological activities. In addition, many of their conjugates have potential for pharmacological use. Here, we present a solid-phase synthesis using our nitrobenzenesulfonyl (Ns) strategy, which can provide 1, 2 and 3 on a gram scale. This approach should be suitable for facile construction of a diverse library of polyamines.

  聚胺类物质，如精胺（1）、热精胺（2）和去甲精胺（3），在自然界中广泛存在，并具有多种生物活性。此外，它们的许多衍生物也具有潜在的药理应用价值。本文中，我们采用硝基苯磺酰（Ns）策略进行固相合成，能够在克级规模上获取化合物1、2和3。这种方法应当适用于便捷构建多样化的聚胺类化合物库。
• Chemical Synthesis and Biological Effect on Xylem Formation of Xylemin and Its Analogues
  作者：Hiroyoshi Takamura、Hiroyasu Motose、Taichi Otsu、Shiori Shinohara、Ryugo Kouno、Isao Kadota、Taku Takahashi

  DOI：10.1002/ejoc.202000322

  日期：2020.5.14

  (6 ) and the analogue N ‐(4‐aminobutyl)cyclopentylamine (21 ) promoted the expression level of thermospermine synthase ACAULIS5 (ACL5 ) and enhanced xylem formation. In addition, xylemin (6 ) was found to significantly promote lateral root formation, whereas xylemin analogues 18 –23 including 21 did not. These results indicate that the analogue 21 has the potential as a novel inhibitor of thermospermine

  Xylemin (6) 及其设计的结构类似物 18-23，N-(4-氨基丁基) 烷基胺，通过 2-硝基苯磺酰胺 (Ns) 策略合成。对 20-23 的改进合成的研究导致从市售的相应酮一步合成这些类似物的发展。合成分子的生物学评估表明，木质素 (6) 和类似物 N-(4-氨基丁基) 环戊胺 (21) 促进了热精胺合酶 ACAULIS5 (ACL5) 的表达水平并增强了木质部的形成。此外，发现木质素 (6) 显着促进侧根形成，而木质素类似物 18 – 23 包括 21 则没有。