benzyl 6-isocyanohexanoate | 244221-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 6-isocyanohexanoate
• CAS: 244221-07-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: PMEWCSIUDOWHBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 6-isocyanohexanoate 、 、 2-(((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid 以 甲醇 为溶剂， 生成 2,3,4,6-tetra-O-acetyl-N-((1R,S)-2-{[6-(benzyloxy)-6-oxohexyl]amino}-2-oxo-1-{[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]methyl}ethyl)-N-{[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]acetyl}-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of multivalent aminoglycoside mimics via the Ugi multicomponent reaction

  摘要：

  使用灵活的Ugi多组分方法合成与2,6-二氨基-2,6-脱氧葡萄糖的多价新寡糖共轭物，从而得到单价、二价和三价的糖类簇。

  DOI：

  10.1039/b501028d

文献信息

• Direct synthesis of sensitive selenocysteine peptides by the Ugi reaction
  作者：Muhammad Abbas、Ludger A. Wessjohann

  DOI：10.1039/c2ob26552d

  日期：——

  Ammonia and selenoaldehydes are both problematic components in Ugi reactions. Here we report the efficient direct multicomponent synthesis of sensitive selenocysteine peptides without the use of convertible (protected) primary amines, including suitable deprotection protocols for selenols.

  氨和硒醛都是 Ugi 反应中的问题成分。在此，我们报告了在不使用可转化（保护）伯胺的情况下直接多组分合成敏感硒半胱氨酸肽的高效方法，包括硒醇的合适脱保护方案。
• One pot synthesis of selenocysteine containing peptoid libraries by Ugi multicomponent reactions in water
  作者：Muhammad Abbas、John Bethke、Ludger A. Wessjohann

  DOI：10.1039/b514597j

  日期：——

  Selenocysteine containing peptoids and peptide–peptoid conjugates were synthesized by combinatorial Ugi-MCRs (multicomponent reactions) in water: for the first time, an acetal (selenoacetal 2a) was used in Ugi-MCR to furnish selenocysteine peptoids in one step as model compounds for selenocysteine peptides and proteins.

  在水中通过组合式 Ugi-MCR（多组分反应）合成了含硒半胱氨酸的类肽和肽-类肽结合物：首次在 Ugi-MCR 中使用缩醛（硒乙缩醛 2a），一步生成硒半胱氨酸类肽，作为硒半胱氨酸肽和蛋白质的模型化合物。
• Multicomponent reactions for the synthesis of multifunctional agents with activity against cancer cells
  作者：Saad Shabaan、Lalla A. Ba、Muhammad Abbas、Torsten Burkholz、Annika Denkert、André Gohr、Ludger A. Wessjohann、Florenz Sasse、Wolfgang Weber、Claus Jacob

  DOI：10.1039/b823149d

  日期：——

  Multicomponent Passerini and Ugi reactions enable the fast and efficient synthesis of redox-active multifunctional selenium and tellurium compounds, of which some show considerable cytotoxicity against specific cancer cells.

  多组分 Passerini 和 Ugi 反应能够快速高效地合成具有氧化还原作用的多功能硒和碲化合物，其中一些化合物对特定癌细胞具有相当强的细胞毒性。
• Novel peptidomimetic compounds containing redox active chalcogens and quinones as potential anticancer agents
  作者：Saad Shaaban、Randi Diestel、Bettina Hinkelmann、Yazh Muthukumar、Rajeshwar P. Verma、Florenz Sasse、Claus Jacob

  DOI：10.1016/j.ejmech.2012.09.033

  日期：2012.12

  Many types of cancer cells are associated with a disturbed intracellular redox balance and oxidative stress (OS). Among the various agents employed to modulate the intracellular redox state of cells, certain redox catalysts containing quinone and chalcogen moieties have shown considerable promise. Passerini multicomponent reaction has been developed for the synthesis of agents combining two, three or even four redox centers in one molecule in a good yield. When incubated with cancer cells these agents inhibited cell proliferation and induced apoptotic cell death. Interestingly, some of these redox active compounds exhibited quite low toxicity with normal cells. The cause was obviously OS, which was reflected by significant decrease in reduced glutathione, subsequently cell cycle arrest and induction of apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.
• PIPERAZINES AS INHIBITORS OF FRUCTOSE-1,6-BISPHOSPHATASE (FBPase)
  申请人：Ontogen Corporation

  公开号：EP1070084A1

  公开（公告）日：2001-01-24