1,6-bis(p-toluenesulfonyloxy)hexane | 4672-50-8

• 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: 1,6-bis(p-toluenesulfonyloxy)hexane
• 英文别名: hexane-1,6-diyl bis(4-methylbenzenesulfonate)；1,6-di(p-toluenesulfonyloxy)hexane；6-(4-methylphenyl)sulfonyloxyhexyl 4-methylbenzenesulfonate
• CAS: 4672-50-8
• 化学式: C₂₀H₂₆O₆S₂
• 分子量: 426.555
• InChiKey: YZYYIAXSSKVOGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-bis(p-toluenesulfonyloxy)hexane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1,6-diazidohexane
  参考文献：
  名称：

  Reduction-Degradable Linear Cationic Polymers as Gene Carriers Prepared by Cu(I)-Catalyzed Azide−Alkyne Cycloaddition

  摘要：

  Linear reduction-degradable cationic polymers with different secondary amine densities (S2 and S3) and their nonreducible counterparts (C2 and C3) were synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) step-growth polymerization of the dialkyne-oligoamine monomers and the diazide monomers. These polymers were studied with a goal of developing a set of new gene carriers. The buffering capacity and DNA binding ability of these polymers were evaluated by acid base titration, gel retardation, and ethidium bromide (EB) exclusion assay. The polymers with lower amine density exhibit a weaker DNA-binding ability but a stronger buffering capacity in the range of pH 5.1 and 7.4. Particle size and zeta-potential measurements demonstrate that the polymers with higher amine density condense pDNA to form polyplexes with smaller sizes, while the disulfide bond in the backbone shows a negative effect on the condensing capability of the polymers, resulting in the formation of polyplexes with large size and nearly neutral surface. The reduction-sensitive polyplexes formed by polymer S2 of S3 can be disrupted by dithiothreitol (DTT) to release free DNA, which has been proven by the combination of gel retardation, EB exclusion assay, particles sizing, and zeta potential measurements. Cell viability measurements by MTT assay demonstrate that the reduction-degradable polymers (S2 and S3) have little cytotoxicity while the nonreducible polymers (C2 and C3) show obvious cytotoxicity, in particular, at high N/P ratios. In vitro transfection efficiencies of these polymers were evaluated using EGFP and luciferase plasmids as the reporter genes. Polymers S3 and S2 show much higher efficiencies than the nonreducible polymers C3 and C2 in the absence of 10% serum; unexpectedly, the lowest transfection efficiency has been observed for polymer S3 in the presence of serum.

  DOI：

  10.1021/bm101005j
• 作为产物：
  描述：

  1,6-己二醇 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 3.0h， 以80%的产率得到1,6-bis(p-toluenesulfonyloxy)hexane
  参考文献：
  名称：

  正电子发射断层成像法合成[ 18 F]标签的（6-氟己基）三苯基phosph阳离子作为心肌成像的潜在剂

  摘要：

  亲脂性阳离子（例如phospho盐）会穿透质膜和线粒体膜的疏水性屏障，并在线粒体内积聚，以响应内部跨膜电位的下降。因此，作为新开发的非侵入性成像剂，[ 18 F]标记的salts盐可以用作分子“电压传感器”探针，以研究线粒体的作用，尤其是在心肌疾病中。本研究报告了通过使用正电子发射断层显像（PET）放射性合成（6-氟己基）三苯基phosph盐（3）作为心肌成像的潜在剂。（6- [ 18 F]氟己基）三苯基phosph盐的参考化合物（[ 18 F] 3通过三步亲核取代反应以74％的收率合成）。在Kryptofix 2.2.2和K 2存在的情况下，通过不加载体的[ 18 F]氟化物与前体己烷-1,6-二烷基双（4-甲基苯磺酸盐）的两步亲核取代反应，对参考化合物进行了放射性标记。CO 3。放射性标记的化合物的合成产率为15–20％。通过分析型HPLC测得的放射化学纯度> 98％，比活度> 6.10–6

  DOI：

  10.1021/bc2004439

文献信息

• Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity
  作者：Fabien Stauffert、Jenny Serra-Vinardell、Marta Gómez-Grau、Helen Michelakakis、Irene Mavridou、Daniel Grinberg、Lluïsa Vilageliu、Josefina Casas、Anne Bodlenner、Antonio Delgado、Philippe Compain

  DOI：10.1039/c7ob00443e

  日期：——

  A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (−)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition

  已经合成了2- O-烷基化的亚氨木糖醇衍生物的两个对映异构体的二聚体和异二聚体文库，并在β-葡萄糖脑苷脂酶（GCase）上进行了评估，该酶是引起高雪氏病（GD）的酶。尽管目的是同时靶向葡糖苷酶的活性位点和次级结合位点，但（-）-2-亚氨基羟醇部分似乎对伊美苷酶抑制有害，并且在G202R，N370S和L444P成纤维细胞中未获得明显的增强。但是，所有具有至少一种（+）-2- O-烷基亚氨木糖醇的化合物都是纳摩尔范围内的GCase抑制剂，并且在G202R纤维刀片中是显着的GCase活性增强剂，这已通过糖基神经酰胺水平的降低和共定位研究得到证实。 。
• Silver(I) Oxide Mediated Highly Selective Monotosylation of Symmetrical Diols. Application to the Synthesis of Polysubstituted Cyclic Ethers
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1021/ol020071y

  日期：2002.7.1

  symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained

  [反应：见正文]在氧化银（I）和催化量的碘化钾存在下，对称二醇和低聚乙二醇与化学计量的对甲苯磺酰氯反应，选择性地导致单甲苯磺酸酯衍生物高产。在用过量的氧化银处理相应的二醇时，容易获得多取代的环醚。基于分子内氢键键合的两个羟基之间的酸度差异来解释高选择性。
• Ring-closing metathesis reaction-based synthesis of new classes of polyether macrocyclic systems
  作者：Naveen、Srinivasarao Arulananda Babu

  DOI：10.1016/j.tet.2015.06.070

  日期：2015.10

  metathesis (RCM) reactions of suitable substrates having terminal olefins, which are assembled from various linkers and hydroxy benzaldehydes and syntheses of a wide range of 16–30 membered, new crown ether-type polyether, aza-polyether, bis aza-polyether macrocycles and dilactone moiety embedded polyether macrocycles (macrolides) are reported. After the ring-closure reaction, installation of different functional

  合适的具有末端烯烃的底物的闭环易位反应（RCM）反应，该底物由各种连接基和羟基苯甲醛组装而成，并合成各种16-30元的新冠醚型聚醚，氮杂-聚醚，双氮杂-聚醚报道了大环和嵌入二内酯部分的聚醚大环（大环内酯）。闭环反应后，使用基于环氧化，氧化和催化加氢的合成转化，在RCM反应中获得的合成聚醚/冠醚大环的外围安装不同的官能团并进行官能团修饰。沿着这条线，已显示出在外围具有环氧化物或α-羟基酮或1,2-二醇官能团的各种聚醚大环的合成。
• Tethered PProDOTs: conformationally restricted 3,4-propylenedioxythiophene based electroactive polymers
  作者：Ryan M. Walczak、John S. Cowart、John R. Reynolds

  DOI：10.1039/b610232h

  日期：——

  Herein we report a complete family of conformationally restricted PProDOT derivatives with varying alkylene tether lengths. It was found that variation of the tether length and structure of the electropolymerizable monomer was successful in the fine-tuning of the electrochemical and optical properties of the subsequent material. It was found that the band gap of the materials could be varied between 1.94 and 2.26 eV, with the “sweet spot” for obtaining the maximum electronic band gap existing at the n = 6 tether length, while maintaining low redox potentials. It was also found that these polymers exhibited stable electrochromic behavior with colors varying from blue–purple to orange in their neutral states and transmissive in their doped states.

  本文报道了一组构象受限的PProDOT衍生物家族，其烷撑链长度各异。研究发现，通过改变链长及电聚合单体的结构，能够成功微调后续材料的电化学和光学性质。材料的带隙可在1.94至2.26电子伏特之间变化，其中最佳链长n=6时可获得最大电子带隙，同时保持较低的氧化还原电位。这些聚合物还表现出稳定的电致变色行为，它们在中性状态下的颜色从蓝紫色到橙色不等，而在掺杂状态下则呈透明态。
• Synthesis, Modification, and Characterization of a Family of Homologues of <i>e</i><i>xo</i>-Calix[4]arene:  <i>e</i><i>xo</i>-[<i>n</i>.<i>m</i>.<i>n</i>.<i>m</i>]Metacyclophanes, <i>n</i>,<i>m</i> ≥ 3
  作者：Dennis H. Burns、Ho−Kit Chan、Jeffrey D. Miller、Charles L. Jayne、David M. Eichhorn

  DOI：10.1021/jo0003044

  日期：2000.8.1

  ring construction in the final step. The exo-[n.m.n.m]metacyclophane ring is conformationally mobile on the NMR time scale, and X-ray crystallography reveals that exo-[3.3.3.3]metacyclophane 2a assumes a cone conformation, and that exo-[6.6.6.6]metacyclophane 6a assumes a chair conformation. Molecular mechanics calculations show that both conformations for each exo-metacyclophane are very similar in energy

  分6步（从2-溴茴香醚开始）制备exo- [nmnm] metacyclophanes族（n，m>或= 3）的一般策略，该方法利用[2 + 2]方法提供exo-描述了具有良好至中等产率的间环苯环。可溶性铜催化剂[CuBr-LiSPh-LiBr-THF]用于在几个合成步骤中有效地偶联格氏试剂和烷基或醚甲苯磺酸盐试剂，包括最后一步中的环结构。exo- [nmnm] metacyclophane环在NMR时间尺度上是构象可移动的，并且X射线晶体学揭示exo- [3.3.3.3] metacyclophane 2a呈现圆锥构象，exo- [6.6.6.6] metacyclophane 6a呈现圆锥构象。椅子的构造。分子力学计算表明，每个exo-metacyclophane的两个构象在能量上都非常相似。