2-吡啶基硫醚 | 4262-06-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-吡啶基硫醚
• 中文别名: 2-吡啶硫化物
• 英文名称: di-2-pyridyl sulfide
• 英文别名: di(pyridin-2-yl)sulfane；2,2'-Thiodipyridine；2-pyridin-2-ylsulfanylpyridine
• CAS: 4262-06-0
• 化学式: C₁₀H₈N₂S
• mdl: MFCD09032910
• 分子量: 188.253
• InChiKey: AQYNZOSCOWGGTP-UHFFFAOYSA-N

物化性质

• LogP：
  2.570 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-吡啶基硫醚 在 potassium tert-butylate 作用下， 以 丙醇 为溶剂， 反应 1.5h， 生成 2-(p-tolylthio)pyridine
  参考文献：
  名称：

  Inoue, Shordoh, Phosphorus and Sulfur and the Related Elements, 1985, vol. 22, p. 141 - 144

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯吡啶 在 二硫化碳 、 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以80%的产率得到2-吡啶基硫醚
  参考文献：
  名称：

  在 [DBUH] + [OAc]存在下，由芳基卤化物和二硫化碳在微波辅助下、无金属和无溶剂合成二芳基硫醚–

  摘要：

  已开发出离子液体 [DBUH]+[OAc]−（DBU = 1,8-二氮杂双环-[5.4.0] undec-7-ene）中芳基卤化物和二硫化碳之间的微波辅助直接偶联。该反应非常有效，以中等至高产率提供相应的二芳基硫醚。芳基氯也可以使用该协议与二硫化碳反应。此外，[DBUH]+[OAc]- 可以很容易地回收并重复使用几次。

  DOI：

  10.3184/174751916x14605556925623
• 作为试剂：
  描述：

  Hoechst acid 、 [3-(吖啶-9-基氨基)-5-氨基苯基]甲醇 在 2-吡啶基硫醚 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以72%的产率得到2'-[4-[3-(9-acridinylamino)-5-hydroxymethylanilino]carbonylpropoxyphenyl]-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole
  参考文献：
  名称：

  Antitumor AHMA Linked to DNA Minor Groove Binding Agents:  Synthesis and Biological Evaluation

  摘要：

  DNA minor groove binder hybrid molecules, netropsin derivatives such as N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide (MePy) or its derivatives containing two units of N-methylpyrrolecarboxamide (diMePy) and bisbenzimidazole (Ho33258), were linked to the NH2 function of AHMA or to the CH2OH group of AHMA-ethylcarbamate to form AHMA-N-netropsins (13-16) and AHMA-ethylcarbamate-O-netropsins (19-22), and AHMA-bis-benzimidazole (AHMA-Ho33258, 25), respectively. These conjugates' in vitro antitumor activity, inhibition of a variety of human tumor cell growth, revealed that AHMA-ethylcarbamate-O-netropsin derivatives were more cytotoxic than AHMA-N-netropsin compounds. In the same studies, all compounds bearing MePy were more potent than those compounds linked with diMePy. Moreover, AHMA-netropsin derivatives bearing a succinyl chain as the linking spacer were more potent than those compounds having a glutaryl bridge. Among these hybrid molecules, AHMA-ethylcarbamate-O-succinyl-MePy (19) was 2- to 6-fold more cytotoxic than the parent compound AHMA (5) in various cell lines, whereas compound 25 had very poor solubility and was inactive. Studies on the inhibitory effect against topoisomerase II (Topo II) and DNA interaction of these conjugates showed no correlation between the potency of DNA binding and inhibitory activity against Topo II.

  DOI：

  10.1021/jm0200714

文献信息

• Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study
  作者：Hsing-Ying Chen、Wei-Te Peng、Ying-Hsien Lee、Yu-Lun Chang、Yen-Jen Chen、Yi-Chun Lai、Nai-Yuan Jheng、Hsuan-Ying Chen

  DOI：10.1021/om400784w

  日期：2013.10.14

  Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be

  先前的研究报道，当前体包括硫粉和使用CuI作为催化剂的芳基卤化物时，S-芳基化反应将生成二芳基二硫化物。但是，我们的研究表明，在上述S-芳基化过程中使用不同的碱会导致联产二芳基硫烷和二芳基二硫烷。另外，我们证明了可以通过选择碱的碱度来控制两种产物的比例。1个1 H NMR谱表明，二芳基二硫醚是第一产物，通过CuI催化与芳基卤化物反应生成二芳基硫烷成为试剂。使用各种不同的碱，对各种芳基卤化物进行了测试，以提高二芳基硫烷和二芳基二硫烷之间的选择性，从而得出以下原理。弱碱，例如金属碳酸盐或乙酸盐，只会产生二芳基二硫醚；强碱（例如金属氢氧化物）会同时生成二芳基二硫烷和二芳基硫烷。根据DFT计算，氢氧根离子被碘离子交换并与铜键合，从而更强烈地影响铜电子以还原二芳基二硫化物。
• Cu-Catalyzed Synthesis of Diaryl Thioethers and <i>S</i>-Cycles by Reaction of Aryl Iodides with Carbon Disulfide in the Presence of DBU
  作者：Peng Zhao、Hang Yin、Hongxin Gao、Chanjuan Xi

  DOI：10.1021/jo400709s

  日期：2013.5.17

  Diaryl thioethers and S-cycles were obtained on the basis of the copper-catalyzed reaction of carbon disulfide and aryl iodides in the presence of DBU. This reaction enables the one-pot synthesis of diaryl thioethers by employing cheap, available, and easy-to-handle carbon disulfide with aryl iodides. The reaction was successfully employed in the construction of sulfur-containing cyclic molecules.

  在DBU存在下，基于二硫化碳和芳基碘化物的铜催化反应，获得了二芳基硫醚和S-环。通过使用廉价，易得且易于处理的二硫化碳与芳基碘化物，该反应能够一锅合成二芳基硫醚。该反应成功地用于构建含硫的环状分子。
• Synthesis of diaryl thioethers from aryl halides and potassium thiocyanate
  作者：Abdol R. Hajipour、Raheleh Pourkaveh、Hirbod Karimi

  DOI：10.1002/aoc.3230

  日期：2014.12

  synthesis of diaryl sufides. A variety of diaryl thioethers were synthesized under relatively mild reaction conditions. This protocol avoids foul‐smelling thiols via cross‐coupling of aryl halides with potassium thiocyanate and all substrates give the corresponding products in good to excellent yields in the presence of low amounts of the catalyst. Copyright © 2014 John Wiley & Sons, Ltd.

  使用尼古丁，苄基氯和氯化钯合成了一种有效的钯催化剂。表征了该催化剂的结构，然后将其用于合成二芳基硫化物。在相对温和的反应条件下合成了多种二芳基硫醚。该方案通过芳基卤化物与硫氰酸钾的交叉偶联避免了难闻的硫醇，并且在存在少量催化剂的情况下，所有底物都能以高至优异的产率获得相应的产物。版权所有©2014 John Wiley＆Sons，Ltd.
• WT1 ANTIGEN PEPTIDE CONJUGATE VACCINE
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：US20150238587A1

  公开（公告）日：2015-08-27

  A compound represented by the formula (1): wherein X a and Y a are each a single bond and the like, cancer antigen peptide A is an MHC class I-restricted WT1 peptide consisting of 7-30 amino acid residues, R 1 is a hydrogen atom, a group represented by the formula (2): wherein X b and Y b are each a single bond and the like, cancer antigen peptide B has a sequence different from that of the cancer antigen peptide A, and is an MHC class I-restricted WT1 peptide consisting of 7-30 amino acid residues, or cancer antigen peptide C, and cancer antigen peptide C has a sequence different from that of the cancer antigen peptide A, and is an MHC class I-restricted WT1 peptide or an MHC class II-restricted WT1 peptide, consisting of 7-30 amino acid residues containing one cysteine residue, or a salt thereof, and the like.

  由公式（1）表示的化合物： 其中Xa和Ya都是单一键等，癌抗原肽A是一种由7-30个氨基酸残基组成的MHC I类限制性WT1肽，R1是一个氢原子，由公式（2）表示的基团： 其中Xb和Yb都是单一键等，癌抗原肽B具有与癌抗原肽A不同的序列，并且是一种由7-30个氨基酸残基组成的MHC I类限制性WT1肽，或者癌抗原肽C，癌抗原肽C具有与癌抗原肽A不同的序列，是一种由7-30个氨基酸残基组成的MHC I类限制性WT1肽或MHC II类限制性WT1肽，含有一个半胱氨酸残基，或其盐类等。
• NiFe₂ O₄ as a magnetically recoverable nanocatalyst for odourless C-S bond formation via the cleavage of C-O bond in the presence of S₈ under mild and green conditions
  作者：Bahareh Atashkar、Amin Rostami、Abed Rostami、Mohammad Ali Zolfigol

  DOI：10.1002/aoc.4691

  日期：2019.3

  nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically

  我们介绍了使用NiFe 2 O 4磁性纳米粒子作为可重复使用的多相纳米催化剂，通过C- O键活化一锅无味地合成不对称和对称二芳基硫化物的绿色方法。不对称硫化物的合成是在碱金属和NiFe 2 O 4磁性纳米粒子存在下，使用酚酸酯（如乙酸酯，三氟甲磺酸酯和甲苯磺酸酯）与芳基硼酸/ S 8或三苯基氯化锡/ S 8作为硫醇化剂的交叉偶联反应进行的作为催化剂，在60-85°C的聚乙二醇溶剂中。同样，使用S 8从酚类化合物合成对称的二芳基硫醚描述了在120℃下在二甲基甲酰胺中作为硫源的NiFe 2 O 4和作为催化剂的NiFe 2 O 4。使用这些方案，由于使用了可磁重复使用的双金属纳米催化剂，并且避免了使用硫醇和芳基卤化物，各种不对称和对称硫化物的合成比使用可用方案更容易。

表征谱图