4,4'-二硫代二丁烷-1-醇 | 30453-20-4

• 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: 4,4'-二硫代二丁烷-1-醇
• 英文名称: 4,4'-dithiodibutanol
• 英文别名: 4,4'-Dithiobisbutan-1-ol；4-(4-hydroxybutyldisulfanyl)butan-1-ol
• CAS: 30453-20-4
• 化学式: C₈H₁₈O₂S₂
• 分子量: 210.362
• InChiKey: RUCLWVAQWOEEPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  9
• 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

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4,4'-二硫代二丁烷-1-醇 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到1-Bromo-4-(4-bromo-butyldisulfanyl)-butane
  参考文献：
  名称：

  Design and synthesis of an aminobenzo-15-crown-5-labeled estradiol tethered with disulfide linkage

  摘要：

  A novel measuring method (electroimmunoassay) of 17beta-estradiol (E,) in urine or blood was proposed on the basis of a competition between E-2 and a labeled E-2 against an immobilizing antibody. To evaluate the principle, 3-{4-[17beta-hydroxy-1,3,5(10)-estratrien-3-yloxy]butyldisulfanyl}-N-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl) succinamic acid (1) was designed and synthesized as a novel aminobenzo-15-crown-5-containing E-2 tethered with disultide linkage. Two thiol-intermediates 5b and 19c were efficiently synthesized from mercaptosuccinic acid 7 and 4,4-dithiodibutyric acid 12, respectively. Formations of disulfide linkages from less reactive thiols were examined and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) could be employed for the formation of an unsymmetrical disulfide 20c from 5b and 19c. Then, removal of TMS- and allyl-protecting groups in 20c successfully afforded the crown ether-containing E-2 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.109
• 作为产物：
  描述：

  4-氯丁醇 在 sodium thiosulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 55.2h， 以5%的产率得到4,4'-二硫代二丁烷-1-醇
  参考文献：
  名称：

  Kinetics of the aqueous periodate oxidation of aliphatic disulfides and thioethers

  摘要：

  DOI：

  10.1021/jo00296a009

文献信息

• Efficient synthesis of unsymmetrical disulfides
  作者：Jaya Kishore Vandavasi、Wan-Ping Hu、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1016/j.tet.2011.09.071

  日期：2011.11

  A novel way of synthesizing unsymmetrical disulfides from thiols with DDQ is presented here. This procedure ran in a straightforward manner to give high product yields. Unsymmetrical disulfides were directly synthesized from the corresponding mixture of thiols in equimolar amounts under mild conditions.

  本文介绍了一种用DDQ从硫醇合成不对称二硫键的新方法。该过程以直接的方式进行以提供高产品收率。在温和条件下，由等摩尔量的相应硫醇混合物直接合成不对称二硫键。
• 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。
• Twisted Push-Pull Probes with Turn-On Sulfide Donors
  作者：Quentin Verolet、Marta Dal Molin、Adai Colom、Aurélien Roux、Laure Guénée、Naomi Sakai、Stefan Matile

  DOI：10.1002/hlca.201600328

  日期：2017.2

  According to Hammett constants, we thought that sulfides could provide access to such a conceptually innovative donor‐acceptor switch. To elaborate on this hypothesis, we here describe the design, synthesis and evaluation of a comprehensive series of twisted push‐pull probes with turn‐on sulfide donors. Their planarization is explored in lipid bilayer membranes of different thickness and fluidity from liquid‐disordered

  可平面化和可极化的二噻吩并[3,2- b ; 2'，3'- d ]噻吩（DTT）二聚体最近作为荧光探针被报道，该荧光探针报道了膜流动性随激发红移，即。在基态平面化。在这项研究中，我们详细阐述了以下假设：在一个非正统取代基的情况下，扭曲推挽式探针可能会发挥最佳性能，该取代基可充当富电子的弱受体和贫电子的芳族化合物的强供体。根据哈米特常数，我们认为硫化物可以为这种概念上创新的供体-受体转换提供途径。为了详细说明这一假设，我们在此描述具有开启的硫化物供体的一系列全面的扭曲推挽式探针的设计，合成和评估。在不同厚度和流动性的脂双层膜中研究了它们的平面化，从液乱相到液序相和固序相。将膜的结果与不同直径的晶体，蛋白质和环糊精大环中的开启机制的平面化进行比较。
• Rhodium-catalyzed phosphorylation reaction of water-soluble disulfides using hypodiphosphoric acid tetraalkyl esters in water
  作者：Mieko Arisawa、Kohei Fukumoto、Masahiko Yamaguchi

  DOI：10.1039/d0ra02377a

  日期：——

  RhCl3 catalyzed the exchange reaction of disulfides and hypodiphosphoric acid tetraalkyl esters in water under homogeneous conditions, which indicated the hypodiphosphoric acid tetraalkyl esters to be novel and efficient phosphorylation reagents in water. The reaction was used in the phosphorylation of unprotected glutathione disulfide.

  RhCl 3在均相条件下催化二硫化物和次磷酸四烷基酯在水中的交换反应，表明次磷酸四烷基酯是一种新型高效的水中磷酸化试剂。该反应用于未保护的谷胱甘肽二硫化物的磷酸化。
• PRODUCTION OF POLYMER HYDROXYLATED AT BOTH TERMINALS, COMPOSITION CONTAINING SAID POLYMER AND ITS USE, AND POLYMER DERIVED FROM SAID COMPOSITION AND ITS USE
  申请人：NIPPON SHOKUBAI CO., LTD.

  公开号：EP0552376A1

  公开（公告）日：1993-07-28

  A process for efficiently producing a polymer hydroxylated at both terminals from a variety of vinyl monomers readily at a low cost, which comprises polymerizing a vinyl monomer (b) by using a radical polymerization initiator (c) in the presence of a compound (a) represented by the general formula HO-A-(S)x-B-OH in such a manner that the reaction system is substantially free from any reactants other than the components (a), (b) and (c), and the amount of the component (a) present in the reaction vessel is at least 50 times by mole as large as that of the component (c) throughout the reaction.

  一种利用各种乙烯基单体以低成本高效生产两端羟基化的聚合物的工艺，该工艺包括在通式 HO-A-(S)x-B-OH 所代表的化合物(a)存在下，通过使用自由基聚合引发剂(c)使乙烯基单体(b)聚合，反应体系中除组分(a)、(b)和(c)外基本上不含任何反应物，并且在整个反应过程中，反应容器中组分(a)的存在量至少是组分(c)的 50 倍（摩尔）、(b)和(c)以外的任何反应物，并且在整个反应过程中，反应容器中存在的组分(a)的量至少是组分(c)的 50 倍（按摩尔计）。