2-benzothiazolyl benzyl disulfide | 27639-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-benzothiazolyl benzyl disulfide
• 英文别名: 2-(benzyldisulfanyl)benzo[d]thiazole；2-(Benzyldisulfanyl)-1,3-benzothiazole
• CAS: 27639-57-2
• 化学式: C₁₄H₁₁NS₃
• 分子量: 289.446
• InChiKey: ZHRUTKMJRWNGFI-UHFFFAOYSA-N

物化性质

• 沸点：
  456.0±38.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-iodobenzyl thioalcohol 、 2-benzothiazolyl benzyl disulfide 以 氯仿 为溶剂， 反应 4.0h， 生成 1-[(Benzyldisulfanyl)methyl]-4-iodobenzene
  参考文献：
  名称：

  Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

  摘要：

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.002
• 作为产物：
  描述：

  2-(p-tolyldisulfanyl)benzo[d]thiazole 在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2-benzothiazolyl benzyl disulfide
  参考文献：
  名称：

  PdCl 2 / DMSO催化的巯基-二硫键交换：不对称二硫键的合成

  摘要：

  通过使用简单的PdCl 2 / DMSO催化系统与对称的二硫化物进行硫醇交换，可以有效地制备不对称的二硫化物。给定的方法具有出色的官能团耐受性，广泛的底物范围和操作简便性。该反应对于诸如肽和药物之类的生物活性支架的后期功能化特别有用。还已经制备了含二硫化物的有机染料。这种转化可以扩展到硫醇-二硒化物或硫醇-二碲化物交换，从而提供RS-SeR'或RS-TeR'。

  DOI：

  10.1021/acs.orglett.1c00858

文献信息

• Direct Allylic C(sp³)–H Thiolation with Disulfides via Visible Light Photoredox Catalysis
  作者：Jungwon Kim、Byungjoon Kang、Soon Hyeok Hong

  DOI：10.1021/acscatal.0c01232

  日期：2020.6.5

  direct allylic C(sp3)–H thiolation mediated by visible light photoredox catalysis. The use of in situ-generated thiyl radical from disulfide as a hydrogen atom transfer (HAT) reagent and a coupling partner enabled selective cleavage of the allylic C(sp3)–H bond followed by C(sp3)–S bond formation. The undesired hydrothiolation, a prevalent reaction from facile thiyl radical addition to olefins, was prevented

  尽管烯丙基硫醚的用途广泛，但直接催化的烯丙基C（sp 3）–H硫醇化仍然难以实现。在这里，我们报告由可见光光氧化还原催化介导的直接烯丙基C（sp 3）–H巯基化作用。使用二硫化物原位生成的硫氢自由基作为氢原子转移（HAT）试剂和偶联伙伴，可以选择性裂解烯丙基C（sp 3）–H键，然后裂解C（sp 3）-S键的形成。通过在碱性条件下立即使巯基去质子化，防止了不希望的加氢硫醇化反应，这是由于容易的巯基自由基加成到烯烃中而引起的普遍反应。各种各样的二芳基二硫化物和烯烃参与了反应，从而高效地生产了烯丙基硫醚。机理研究表明，光催化剂作为氧化还原介体参与其中，这对于将烯丙基从自由基转化为烯丙基阳离子以及进一步的离子偶联过程至关重要。基于提出的机理，通过合理设计的更易还原的不对称二硫化物解决了烷基烯丙基硫醚合成的局限性，从而使所需的催化循环有效。
• Copper(I) Iodide Catalyzed 3-Sulfenylation of Indoles with Unsymmetric Benzothiazolyl-Containing Disulfides at Room Temperature
  作者：Yunyang Wei、Wenlei Ge

  DOI：10.1055/s-0031-1289705

  日期：2012.3

  A highly efficient protocol for the synthesis of 3-sulfenylindoles in moderate to excellent yields via the reaction of indoles with unsymmetric benzothiazolyl-containing disulfides is described. Copper(I) iodide is used as the catalyst and the reactions take place at room temperature. The by-product, 2-mercaptobenzothiazole, can be easily recovered and reused.

  描述了一种高效的合成3-硫烯基吲哚的协议，该方法通过吲哚与不对称的苯并噻唑基二硫化物反应，获得中等到优良的产率。氯化铜(I)被用作催化剂，反应在室温下进行。副产物二巯基苯并噻唑可以被轻松回收和再利用。
• Synthesis of Unsymmetric Trisulfides from 9-Fluorenylmethyl Disulfides
  作者：Shi Xu、Yingying Wang、Miles N. Radford、Aaron J. Ferrell、Ming Xian

  DOI：10.1021/acs.orglett.7b03846

  日期：2018.1.19

  A convenient method for the preparation of unsymmetrical trisulfides using 9-fluorenylmethyl (Fm) disulfide as the precursors is reported. This method gives the desired trisulfides in good yields under mild conditions.

  报道了一种使用9-芴基甲基（Fm）二硫化物作为前体制备不对称三硫化物的简便方法。该方法在温和的条件下以良好的收率得到所需的三硫化物。
• Visible-Light-Driven Iodine-Catalyzed Synthesis of Unsymmetrical Disulfides via Oxidative Coupling
  作者：Ming-Zhe Ren、Yan-Jun Fu、Zheng-Jun Quan、Xi-Cun Wang、Bo-Sheng Zhang

  DOI：10.1055/s-0042-1751433

  日期：——

  Herein, a facile and environmentally friendly oxidative coupling reaction to obtain unsymmetrical disulfide compounds, without using metal or organic dyes as photocatalyst and only using a catalytic amount of iodine, was developed. Oxygen is used as oxidant in the reaction and the substrate scope is wide. A gram-scale synthesis also highlights the synthetic practicality of this photochemical strategy

  在此，开发了一种简便且环境友好的氧化偶联反应，无需使用金属或有机染料作为光催化剂，仅使用催化量的碘即可获得不对称二硫化物。反应以氧为氧化剂，底物范围广。克级合成也突出了这种光化学策略的合成实用性。此外，我们的机理研究支持通过自由基偶联形成二硫化物产物。
• Disulfides. 1. Syntheses Using 2,2'-Dithiobis(benzothiazole)
  作者：Ewa Brzezinska、Andrew L. Ternay

  DOI：10.1021/jo00105a048

  日期：1994.12

  2,2'-Dithiobis(benzothiazole) produces unsymmetric disulfides containing the 2-benzothiazolyl fragment in both high yield and purity when reacted with 1 equiv of a variety of alkane and arene thiols under mild conditions. In turn, these unsymmetric disulfides react with a variety of thiols to produce either symmetric disulfides or new unsymmetric disulfides in excellent yields. At room temperature, 2 equiv of most thiols are oxidized essentially quantitatively to the corresponding symmetric disulfide by 2,2'-dithiobis(benzothiazole). Thiols employed at various stages include 1-propanethiol, 2-propanethiol, 2-methyl-2-propanethiol, phenylmethanethiol, 2-mercaptoethanol, 2-mercaptoethylamine (MEA) hydrochloride, 2-methoxybenzenethiol, 4-methoxybenzenethiol, 4-aminobenzenethiol, 4-acetamidobenzenethiol, 4-bromobenzenethiol , 4-methylbenzenethiol, N-acetyl-L-cysteine, and sodium 2-mercaptoethanesulfonate (MESNA). Various disulfides were inactive in vivo against cyanide poisoning.