1,6-bis(aminooxy)henane | 91219-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-bis(aminooxy)henane
• 英文别名: 1,6-bis(aminooxy)hexane；O,O'-hexane-1,6-diyl-bis-hydroxylamine；1,6-bis-aminooxy-hexane；1,6-Bis-aminooxy-hexan；O.O'-Hexamethylen-dihydroxylamin；Bis-1,6-amino-oxyhexan；O-(6-aminooxyhexyl)hydroxylamine
• CAS: 91219-68-0
• 化学式: C₆H₁₆N₂O₂
• 分子量: 148.205
• InChiKey: PUOHESNZULSWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-bis(aminooxy)henane 在 N,N'-羰基二咪唑 作用下， 反应 1.25h， 生成 2-Amino-N-[6-(2-amino-acetylaminooxy)-hexyloxy]-acetamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Johnson; Boxer; Drummond, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 4, p. 432 - 437

  摘要：

  DOI：
• 作为产物：
  描述：

  1,6-二溴己烷 在 三乙胺 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-bis(aminooxy)henane
  参考文献：
  名称：

  Uracil-Directed Ligand Tethering:  An Efficient Strategy for Uracil DNA Glycosylase (UNG) Inhibitor Development

  摘要：

  Uracil DNA glycosylase (UNG) is an important DNA repair enzyme that recognizes and excises uracil bases in DNA using an extrahelical recognition mechanism. It is emerging as a desirable target for small-molecule inhibitors given its key role in a wide range of biological processes including the generation of antibody diversity, DNA replication in a number of viruses, and the formation of DNA strand breaks during anticancer drug therapy. To accelerate the discovery of inhibitors of UNG we have developed a uracil-directed ligand tethering strategy. In this efficient approach, a uracil aldehyde ligand is tethered via alkyloxyamine linker chemistry to a diverse array of aldehyde binding elements. Thus, the mechanism of extrahelical recognition of the uracil ligand is exploited to target the UNG active site, and alkyloxyamine linker tethering is used to randomly explore peripheral binding pockets. Since no compound purification is required, this approach rapidly identified the first small-molecule inhibitors of human UNG with micromolar to submicromolar binding affinities. In a surprising result, these uracil-based ligands are found not only to bind to the active site but also to bind to a second uncompetitive site. The weaker uncompetitive site suggests the existence of a transient binding site for uracil during the multistep extrahelical recognition mechanism. This very general inhibitor design strategy can be easily adapted to target other enzymes that recognize nucleobases, including other DNA repair enzymes that recognize other types of extrahelical DNA bases.

  DOI：

  10.1021/ja055846n

文献信息

• Synthesis and Characterization of Five Bisoxime-Type Chelating Ligands Based on Bis(aminooxy)alkane and 2-Naphthaldehyde
  作者：Gang Li、Su-Xia Gao、Zong-Li Ren、Na We、Li Wang、Xiu-Yan Dong

  DOI：10.14233/ajchem.2014.17492

  日期：——

  Five bisoxime chelating ligands L1-L5 have been synthesized from 2-naphthaldehyde and 1,2-bis(aminooxy)ethane, 1,3-bis(aminooxy)-propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane and 1,6-bis(aminooxy)hexane in hot ethanolic medium, respectively and characterized by elemental analyses, IR, UV-visible spectra and 1H NMR spectroscopy. The bisoxime chelating ligands L1-L5 may be promising units for the construction of supramolecular metal complexes.

  在热乙醇介质中，以 2-萘甲醛和 1,2-双（氨基氧）乙烷、1,3-双（氨基氧）丙烷、1,4-双（氨基氧）丁烷、1,5-双（氨基氧）戊烷和 1,6-双（氨基氧）己烷为原料，分别合成了五种双肟螯合配体 L1-L5，并通过元素分析、红外光谱、紫外可见光谱和 1H NMR 光谱对其进行了表征。双肟螯合配体 L1-L5 可能是构建超分子金属配合物的有前途的单元。
• Synthesis and Characterization of Bromo-Substituted Salamo-Type Bisoxime Compounds Series
  作者：Li Xu、Na Li、Yang Zhang、Na Wen、Li-Chun Zhu、Xiu-Yan Dong

  DOI：10.14233/ajchem.2014.17398

  日期：——

  Four novel bromo-substituted Salamo-type bisoxime compounds H2L1-H2L4 have been synthesized from 5-bromo-2-hydroxybenzaldehyde and 1,3-bis(aminooxy)propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane or 1,6-bis(aminooxy)henane in hot ethanolic medium, respectively and characterized by elemental analyses, IR, UV-visible spectra and 1H NMR spectroscopy.

  以5-溴-2-羟基苯甲醛和1,3-双(氨氧基)丙烷、1,4-双(氨氧基)丁烷、1,5-双为原料合成了四种新型溴取代Salamo型双肟化合物H2L1-H2L4分别在热乙醇介质中的（氨基氧基）戊烷或 1,6-双（氨基氧基）己烷，并通过元素分析、红外、紫外-可见光谱和 1H NMR 光谱进行表征。
• Synthesis and Characterization of Methoxy-Substituted Salamo-Type Bisoximes Based on Bis(aminooxy)alkane and 3-Methoxy-2-hydroxybenzaldehyde
  作者：Zong-Li Ren、Su-Xia Gao、Yang Zhang、Li Wang、Xiu-Yan Dong

  DOI：10.14233/ajchem.2014.17468

  日期：——

  Four new methoxy-substituted Salamo-type bisoxime compounds 6,6-dimethoxy-2,2-[(propylene-1,3-diyldioxy)bis(nitrilo-methylidyne)]diphenol (H2L1), 6,6-dimethoxy-2,2-[(butylene-1,4-diyldioxy)bis(nitrilomethylidyne)]diphenol (H2L2), 6,6-dimethoxy-2,2-[(propane-1,5-diyldioxy)bis(nitrilome-thylidyne)]diphenol (HH2L3) and 6,6-dimethoxy-2,2-[(hexane-1,6-diyldioxy)bis(nitrilo-methylidyne)]diphenol (H2L4) have been synthesized through condensation reactions under hot ethanol medium, respectively and characterized by elemental analyses, IR, UV-visible and 1H NMR spectra.

  四种新的甲氧基取代的萨拉莫型双肟化合物6,6-二甲氧基-2,2-[(丙烯-1,3-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L1)、6,6-二甲氧基-2、 2-[(丁烯-1,4-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L2)、6,6-二甲氧基-2,2-[(丙烷-1,5-二基二氧基)双(次氮基亚甲基)]联苯酚(HH2L3)和6,6-二甲氧基-2,2-[(己烷-1,6-二基二氧基)双(次氮基亚甲基)]联苯酚(H2L4)分别在热乙醇介质下通过缩合反应合成，并表征为元素分析、红外光谱、紫外-可见光谱和 1H NMR 光谱。
• Synthesis and Characterization of Salamo-type Bisoximes Based on 3-Ethoxysalicyladehyde and Bis(aminooxy)alkane
  作者：Gang Li、Jian-Chun Ma、Zong-Li Ren、Wei-Min Zhou、Li Wang、Na Wen

  DOI：10.14233/ajchem.2015.17557

  日期：——

  A series of ethoxy-substituted Salamo-type bisoximes H2L1-H2L4 have been synthesized from 3-ethoxysalicyladehyde and 1,3-bis(aminooxy)propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane or 1,6-bis(aminooxy)hexane in hot ethanol medium, respectively and characterized by elemental analyses, IR, UV-visible spectra and 1H NMR spectroscopy. Salamo-type compounds are conducive to coordinate experiments and construct supramolecular complexes.

  在热乙醇介质中，分别从 3-乙氧基水杨醛和 1,3-双（氨基氧基）丙烷、1,4-双（氨基氧基）丁烷、1,5-双（氨基氧基）戊烷或 1,6-双（氨基氧基）己烷合成了一系列乙氧基取代的萨拉莫型双肟 H2L1-H2L4，并通过元素分析、红外光谱、紫外可见光谱和 1H NMR 光谱进行了表征。萨拉莫类化合物有利于进行配位实验和构建超分子复合物。
• Synthesis and Characterization of Multihalogen Substituted Salamo-Type Bisoximes
  作者：Yu-Hua Yang、Xiu-Yan Dong、Yu-Jie Zhang、Gang Li、Meng-Meng Zhao

  DOI：10.14233/ajchem.2014.15925

  日期：——

  Four tetrahalogen substituted Salamo-type bisoximes H2L1-H2L4 have been synthesized from 3-bromo-5-chloro-2-hydroxybenzaldehyde and 1,3-bis(aminooxy)propane, 1,4-bis(aminooxy)butane, 1,5-bis(aminooxy)pentane or 1,6-bis(aminooxy)hexane in ethanol solution, respectively and characterized by elemental analyses as well as IR, UV-visible and 1H NMR spectroscopy.

  四种四卤素取代的萨拉莫型双氧肟 H2L1-H2L4 分别由 3-溴-5-氯-2-羟基苯甲醛和乙醇溶液中的 1,3-双（氨基氧基）丙烷、1,4-双（氨基氧基）丁烷、1,5-双（氨基氧基）戊烷或 1,6-双（氨基氧基）己烷合成，并通过元素分析以及红外光谱、紫外可见光谱和 1H NMR 光谱进行了表征。