6,6'-二硫烷二基二(1-己醇) | 80901-86-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 中文名称: 6,6'-二硫烷二基二(1-己醇)
• 英文名称: 6,6'-disulfanediyldihexan-1-ol
• 英文别名: 6,6'-disulfanediylbis(hexan-1-ol)；bis(6-hydroxyhexyl) disulfide；Bis(6-hydroxyhexyl)disulfide；6-(6-hydroxyhexyldisulfanyl)hexan-1-ol
• CAS: 80901-86-6
• 化学式: C₁₂H₂₆O₂S₂
• 分子量: 266.469
• InChiKey: HPKCPHUCATZKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6'-二硫烷二基二(1-己醇) 在 三苯基膦 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成 1,2'-bis (6-bromohexyl)disulfan
  参考文献：
  名称：

  Rational size control of gold nanoparticles employing an organometallic precursor [Au-C≡C- t-Bu]₄ and tunable thiolate-functionalized ionic liquids in organic medium

  摘要：

  用有六种不同硫醇功能化离子液体（TFILs）稳定的金纳米颗粒（Au NPs）在有机溶剂中合成。通过改变TFIL稳定的Au NPs的N-烷基链长度和（或）TFIL稳定配体的对阴离子，可以合理控制其大小和光学性质。Au NPs是通过在不同二硫化物前体存在下，用NaBH₄还原金前体（HAuCl₄或[Au-C≡C-t-Bu]₄）制备的。基于Israelachvili理论提出了一个模型，用于解释NP大小与N-烷基链长度和表面活性剂类TFIL稳定剂的对阴离子依赖性。

  DOI：

  10.1139/v11-146
• 作为产物：
  描述：

  6-溴正己醇 在 碘 、 硫脲 作用下， 以 乙醇 为溶剂， 生成 6,6'-二硫烷二基二(1-己醇)
  参考文献：
  名称：

  Rational size control of gold nanoparticles employing an organometallic precursor [Au-C≡C- t-Bu]₄ and tunable thiolate-functionalized ionic liquids in organic medium

  摘要：

  用有六种不同硫醇功能化离子液体（TFILs）稳定的金纳米颗粒（Au NPs）在有机溶剂中合成。通过改变TFIL稳定的Au NPs的N-烷基链长度和（或）TFIL稳定配体的对阴离子，可以合理控制其大小和光学性质。Au NPs是通过在不同二硫化物前体存在下，用NaBH₄还原金前体（HAuCl₄或[Au-C≡C-t-Bu]₄）制备的。基于Israelachvili理论提出了一个模型，用于解释NP大小与N-烷基链长度和表面活性剂类TFIL稳定剂的对阴离子依赖性。

  DOI：

  10.1139/v11-146

文献信息

• Hypervalent Iodine(III)-Promoted Metal-Free S-H Activation: An Approach for the Construction of S-S, S-N, and S-C Bonds
  作者：Eakkaphon Rattanangkool、Watanya Krailat、Tirayut Vilaivan、Preecha Phuwapraisirisan、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1002/ejoc.201402180

  日期：2014.8

  thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75–95 %) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides

  在对称二硫化物和次磺酰胺的制备中，已经探索了用（二乙酰氧基碘）苯 (DIB) 活化硫醇的硫原子。用 DIB 处理硫醇后，二硫化物可以以极好的收率 (75–95%) 产生。在室温下反应在不到五分钟内完成。脂肪族、芳香族和杂芳香族硫醇与这种转化相容。此外，从杂芳族硫醇获得的杂芳族二硫化物在碱存在下进一步与亲核胺反应，以一锅法以相当到良好的产率（43-90%）提供相应的次磺酰胺。该方法成功地扩展到吲哚作为一种代表性的富电子芳香化合物，从而可以在一锅中成功构建 S-C 键。
• Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis
  作者：Hiroki Iida、Marina Oka、Ryo Kozako

  DOI：10.1055/a-1520-9916

  日期：2021.7

  molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.

  使用核黄素衍生的有机催化剂和分子碘的耦合催化成功地促进了硫醇在无金属温和条件下有氧氧化成二硫化物。通过将电子从碘催化剂转移到仿生黄素催化剂，分子氧的活化在室温下顺利发生，形成了硫醇绿色氧化合成二硫化物的基础。
• Reversibility of the thia-Michael reaction of cytotoxic C₅-curcuminoid and structure–activity relationship of bis-thiol-adducts thereof
  作者：Aki Kohyama、Michihiro Fukuda、Shunsuke Sugiyama、Hiroyuki Yamakoshi、Naoki Kanoh、Chikashi Ishioka、Hiroyuki Shibata、Yoshiharu Iwabuchi

  DOI：10.1039/c6ob01771a

  日期：——

  investigated the reversibility of the thia-Michael reaction of 1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one, named GO-Y030 which is the most potent cytotoxic C5-curcuminoid, using spectroscopic methods. A panel of GO-Y030-bis-thiol-adducts were synthesized and the structure–reactivity relationship regarding the retro thia-Michael reaction as well as the cell growth inhibitory activity against

  C 5-姜黄素类[又名双（芳基亚甲基）丙酮]是姜黄素类似物，其具有反应性交联的二烯酮结构，对于引发细胞毒性是必不可少的。为了深入了解C 5-姜黄素的作用方式，我们研究了1,5-双（3,5-双（甲氧基甲氧基）苯基）-1,4-戊二烯-3-的硫-迈克尔反应的可逆性一种，使用光谱学方法命名为GO-Y030，它是最有效的细胞毒性C 5-姜黄素。合成了一组GO-Y030-双-硫醇加合物，并评估了与逆硫-迈克尔反应的结构反应关系以及对人结肠癌HCT116的细胞生长抑制活性。一些C 5-姜黄素硫醇加合物显示出与GO-Y030相当的细胞毒性，证明了它们作为前药的潜在用途。这些结果暗示，C 5-姜黄素类化合物通过可逆的thia-Michael反应与各种生物硫醇共价相互作用而引起细胞毒性。
• Transition Metal-Catalyzed Synthesis of (E)-2-(Alkylthio)alka-1,3-dienes from Allenes and Dialkyl Disulfides with Concomitant Hydride Transfer
  作者：Mieko Arisawa、Atsushi Suwa、Kenji Fujimoto、Masahiko Yamaguchi

  DOI：10.1002/adsc.200303010

  日期：2003.5

  Reaction of dialkyl disulfides or diselenides with allenes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (E)-2-alkylthio(seleno)-1,3-dienes and (E)-2-alkylthio(seleno)-2-alkenes. Unlike the reaction of alkynes, the reaction of allene is accompanied by hydride transfer.

  铑-膦配合物和三氟甲磺酸催化二烷基二硫化物或二硒化物与丙二烯的反应，得到（E）-2-烷基硫代（硒代）-1,3-二烯和（E）-2-烷基硫代（硒代）-2-烯烃。与炔烃的反应不同，丙二烯的反应伴随有氢化物转移。
• Targeting DNA with “light-up” pyrimidine triple-helical forming oligonucleotides conjugated to stabilizing fluorophores (LU-TFOs)
  作者：Brice-Loïc Renard、Rémy Lartia、Ulysse Asseline

  DOI：10.1039/b813289e

  日期：——

  The synthesis of triple-helix-forming oligonucleotides (TFOs) linked to a series of cyanine monomethines has been performed. Eight cyanines including one thiocyanine, four thiazole orange analogues, and three quinocyanines were attached to the 5′-end of 10-mer pyrimidine TFOs. The binding properties of these modified TFOs with their double-stranded DNA target were studied by absorption and steady-state fluorescence spectroscopy. The stability of the triplex structures depended on the cyanine structure and the linker size used to connect both entities. The most efficient cyanines able to stabilize the triplex structures, when attached at the 5′-end of the TFO, have been incorporated at both ends and provided triplex structures with increased stability. Fluorescence studies have shown that for the TFOs involving one cyanine, an important intensity increase (up to 37-fold) in the fluorescent signal was observed upon their hybridization with the double-stranded target, proving hybridization. The conjugates involving thiazole orange attached by the benzothiazole ring provided the most balanced properties in terms of triplex stabilization, fluorescence intensity and fluorescence enhancement upon hybridization with the double-stranded target. In order to test the influence of different parameters such as the TFO sequence and length, thiazole orange was used to label 17-mer TFOs. Hybridizations of these TFOs with different duplexes, designed to study the influence of mismatches at both internal and terminal positions on the triplex structures, confirmed the possibility of triplex formation without loss of specificity together with a strong fluorescence enhancement (up to 13-fold).

  合成了一系列与青烯单甲基化合物连接的三重螺旋形成寡核苷酸（TFOs）。在10个碱基的嘧啶TFO的5'末端连接了八种青烯，包括一种硫氰酸盐、四种噻唑橙类类似物和三种喹啉青烯。通过吸收光谱和稳态荧光光谱研究了这些修饰TFO与其双链DNA靶标的结合特性。三重螺旋结构的稳定性取决于青烯的结构和用于连接两个实体的连接剂尺寸。当青烯附加在TFO的5'末端时，最有效的青烯能够稳定三重螺旋结构，并在两端合并，提高了三重螺旋结构的稳定性。荧光研究表明，对于涉及一种青烯的TFO，在与双链靶标杂交时，荧光信号的重要强度增加（最高可达37倍）表明了杂交的发生。通过苯噻唑环连接的噻唑橙类共轭物在三重螺旋稳定性、荧光强度和与双链靶标杂交时的荧光增强方面提供了最平衡的特性。为了测试不同参数（如TFO序列和长度）的影响，使用噻唑橙对17个碱基的TFO进行标记。这些TFO与不同的双链进行杂交，以研究内部和末端位置错配对三重螺旋结构的影响，证实了在不失去特异性的情况下形成三重螺旋的可能性，同时伴随强烈的荧光增强（最高可达13倍）。