N-[(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-dimethylamino]naphthalen-1-sulfonamide | 914311-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-dimethylamino]naphthalen-1-sulfonamide
• 英文别名: N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide；NH2-TTEG-NH-DNS；N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 914311-67-4
• 化学式: C₂₀H₃₁N₃O₅S
• 分子量: 425.549
• InChiKey: ZYIWHRHQRVNEKU-UHFFFAOYSA-N

物化性质

• 沸点：
  590.9±60.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-dimethylamino]naphthalen-1-sulfonamide 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3-(1-(5-(dimethylamino)naphthalene-1-sulfonamido)-13-oxo-3,6,9-trioxa-12-azahexadecanamido)phenyl)boronic acid
  参考文献：
  名称：

  Metabolic alkene labeling and in vitro detection of histone acylation via the aqueous oxidative Heck reaction

  摘要：

  EDTA-Pd(II)作为一种新型催化剂，通过水相氧化Heck反应实现蛋白质标记。

  DOI：

  10.1039/c4ob02502d
• 作为产物：
  描述：

  1-叠氮基-2-{2-[2-(2-叠氮基乙氧基)乙氧基]乙氧基}乙烷 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 N-[(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-5-dimethylamino]naphthalen-1-sulfonamide
  参考文献：
  名称：

  A Convenient Route to Diversely Substituted Icosahedral Closomer Nanoscaffolds

  摘要：

  The design and synthesis of icosahedral polyhedral borane closomer motifs based upon carbonate and carbamate anchoring groups for biomedical applications are described. Dodecacarbamate closomers containing easily accessible groups of interest at their linker termini were synthesized via activation of the B-OH vertices as aryl carbonates and their subsequent reaction with primary amines. Novel dodecacarbonate closomers were successfully synthesized for the first time by reacting [closo-B(12)(OH)(12)](2-) with an excess of respective aryl chloroformates, utilizing relatively short reaction times, mild conditions and simple purification strategies, all of which had previously presented difficulties in closomer chemistry. This methodology for the 12-fold degenerate synthesis of carbonate and carbamate closomers will greatly facilitate further exploration of closomers as monodisperse nanomolecular delivery platforms.

  DOI：

  10.1021/ja204488p

文献信息

• A “Catch-and-Release” Protocol for Alkyne-Tagged Molecules Based on a Resin-Bound Cobalt Complex for Peptide Enrichment in Aqueous Media
  作者：Ayako Miyazaki、Miwako Asanuma、Kosuke Dodo、Hiromichi Egami、Mikiko Sodeoka

  DOI：10.1002/chem.201400056

  日期：2014.6.23

  and mild protocols for the specific enrichment of biomolecules is of significant interest from the perspective of chemical biology. A cobalt–phosphine complex immobilised on a solid‐phase resin has been found to selectively bind to a propargyl carbamate tag, that is, “catch”, under dilute aqueous conditions (pH 7) at 4 °C. Upon acidic treatment of the resulting resin‐bound alkyne–cobalt complex, the Nicholas

  从化学生物学的观点出发，对于生物分子的特异性富集的新的和温和的方案的开发引起了极大的兴趣。已发现固定在固相树脂上的钴膦复合物在4°C的稀水条件（pH 7）下选择性地结合到炔丙基氨基甲酸酯标签上，即“捕获”。在对所得的与树脂结合的炔-钴络合物进行酸性处理后，引发了尼古拉斯反应，以游离胺的形式从树脂中“释放”了炔标记的分子。模型研究表明，可以在4°C的条件下实现对炔烃标记分子的选择性富集。概念验证适用于带有炔烃标记的氨基酸和二肽。使用炔烃标记的二肽进行的研究证明，该方案与在侧链中具有一系列功能的各种氨基酸兼容。此外，在各种肽存在下，选择性富集和检测衍生自炔烃标记的二肽的“捕获和释放”的胺已在高度稀释的条件下完成（如质谱法所测定）。
• Catch and release of alkyne-tagged molecules in water by a polymer-supported cobalt complex
  作者：Hiromichi Egami、Shinji Kamisuki、Kosuke Dodo、Miwako Asanuma、Yoshitaka Hamashima、Mikiko Sodeoka

  DOI：10.1039/c1ob06123b

  日期：——

  A cobalt–phosphine complex supported on PS-PEG beads was found to react with a propargyl carbamate tag, and the tagged molecules immobilized on the beads could be released by acidic treatment through the Nicholas reaction pathway. These reactions work in aqueous media at 4 °C, so that this catch and release procedure is compatible with conditions generally used in biochemical experiments.

  一种以PS-PEG微珠为支撑的钴-膦复合物被发现能够与丙炔基氨基甲酸酯标签反应，固定在微珠上的标记分子可以通过酸性处理通过尼古拉斯反应途径释放。这些反应在4℃的水性介质中进行，因此这一捕获与释放的过程与生化实验中通常使用的条件兼容。
• Synthesis of novel dansyl-labeled Celecoxib derivatives
  作者：Andreas Lill、Klaus Scholich、Holger Stark

  DOI：10.1016/j.tetlet.2013.09.025

  日期：2013.12

  Four novel dansyl-labeled derivatives of Celecoxib, a cyclooxygenase-2 (COX-2) selective inhibitor, were designed and synthesized. To realize the fluorophore-linker-approach divergent and convergent synthetic strategies were applied. Therefore Celecoxib p-benzoic acid, 8, was synthesized in a new and convenient way. The yield and the synthetic route to Celecoxib, 1, its pyrazolylic acid, 7, and its pyrazolylic methyl ester, 6, were improved. Through a convenient synthesis 1,11-diamino-3,6,9-trioxundecane, 19, was obtained in high yield and purity and used as a linker for the dansyl moiety. (C) 2013 Elsevier Ltd. All rights reserved.
• Metabolic alkene labeling and in vitro detection of histone acylation via the aqueous oxidative Heck reaction
  作者：Maria E. Ourailidou、Paul Dockerty、Martin Witte、Gerrit J. Poelarends、Frank J. Dekker

  DOI：10.1039/c4ob02502d

  日期：——

  EDTA-Pd(ii) as a novel catalyst for protein labeling via the aqueous oxidative Heck reaction.

  EDTA-Pd(II)作为一种新型催化剂，通过水相氧化Heck反应实现蛋白质标记。
• A Convenient Route to Diversely Substituted Icosahedral Closomer Nanoscaffolds
  作者：Satish S. Jalisatgi、Vikas S. Kulkarni、Betty Tang、Zachary H. Houston、Mark W. Lee、M. Frederick Hawthorne

  DOI：10.1021/ja204488p

  日期：2011.8.17

  The design and synthesis of icosahedral polyhedral borane closomer motifs based upon carbonate and carbamate anchoring groups for biomedical applications are described. Dodecacarbamate closomers containing easily accessible groups of interest at their linker termini were synthesized via activation of the B-OH vertices as aryl carbonates and their subsequent reaction with primary amines. Novel dodecacarbonate closomers were successfully synthesized for the first time by reacting [closo-B(12)(OH)(12)](2-) with an excess of respective aryl chloroformates, utilizing relatively short reaction times, mild conditions and simple purification strategies, all of which had previously presented difficulties in closomer chemistry. This methodology for the 12-fold degenerate synthesis of carbonate and carbamate closomers will greatly facilitate further exploration of closomers as monodisperse nanomolecular delivery platforms.