2,3,5-三硫杂己烷 | 42474-44-2

• 物质功能分类: 香精与香料 - 合成香料 - 硫醚类香料
• 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: 2,3,5-三硫杂己烷
• 英文名称: 2,3,5-trithiahexane
• 英文别名: methyl (methylthio)methyl disulfide；2,3,5-Trithiahexan；(methyldisulfanyl)-methylsulfanylmethane
• CAS: 42474-44-2
• 化学式: C₃H₈S₃
• 分子量: 140.295
• InChiKey: MYIOBINSHMEDEY-UHFFFAOYSA-N

物化性质

• 沸点：
  182℃
• 密度：
  1.169
• 闪点：
  63℃
• LogP：
  2.42
• 物理描述：
  Clear almost colourless liquid; powerful, penetrating aroma, reminiscent of onion
• 溶解度：
  Insoluble in water and heptane; soluble in triacetin
• 折光率：
  1.436-1.444
• 保留指数：
  1106;1097;1094;1104;1109;1110;1139

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  6
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,5-trithiahexane 5-oxide 在 triethyloxonium fluoroborate 、 sodium hydrogensulfite 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,5-三硫杂己烷
  参考文献：
  名称：

  Chemistry of alkyl thiosulfinate esters. VII. Mechanistic studies and synthetic applications

  摘要：

  DOI：

  10.1021/ja00819a034

文献信息

• Novel Disulfides with Antitumour Efficacy and Specificity
  作者：Rebecca Griffiths、W. Wei-Lynn Wong、Stephen P. Fletcher、Linda Z. Penn、Richard F. Langler

  DOI：10.1071/ch03105

  日期：——

  Some disulfides have previously been shown to possess antifungal and/or antileukaemic activity. Importantly, this cytotoxicity can be selective. We have previously shown that a subset of these compounds does not block the proliferative potential of normal, non-transformed cells. Based on these results and proposed mechanisms of action, a new set of structurally modified organosulfur compounds, including α-substituted disulfides and a thiosulfonate ester, have been prepared and evaluated for their potential as antileukaemic agents. Compounds were screened for antiproliferative activity against a panel of human cells derived from acute lymphocytic and acute myelogenous leukaemia, as well as non-transformed cells. We have identified five new disulfides and a thiosulfonate that can trigger tumour cells to undergo cell death by an apoptotic mechanism in a sensitive and specific manner.

  一些二硫化物先前已被证明具有抗真菌和/或抗白血病活性。重要的是，这种细胞毒性具有选择性。我们之前已经证明，这些化合物中的一个子集不会阻碍正常、非转化细胞的增殖潜力。根据这些结果和提出的作用机制，我们制备了一组新的结构修饰型有机硫化合物，包括α-取代二硫化物和硫代磺酸酯，并对其作为抗白血病药物的潜力进行了评估。我们对来自急性淋巴细胞白血病和急性髓性白血病以及非转化细胞的一系列人类细胞进行了化合物抗增殖活性筛选。我们发现了五种新的二硫化物和一种硫代磺酸盐，它们能以敏感而特异的方式引发肿瘤细胞通过凋亡机制死亡。
• Sulfur containing compounds
  申请人：——

  公开号：US20030220524A1

  公开（公告）日：2003-11-27

  This invention is directed to novel and known stufur containing compounds and pharmaceutically acceptable salts thereof that have utility as antifungals and as antiproliferative agents against mammalian cells, in particular cancer cells and most particularly leukemia-derived cells. The invention provides a method for synthesizing certain of the sulfur containing compounds that is more efficient than previously known methods.

  这项发明涉及新颖且已知的含有硫的化合物以及具有抗真菌活性和作为哺乳动物细胞，特别是癌细胞，尤其是白血病来源细胞的抗增殖剂的药用可接受盐。发明提供了一种合成某些含硫化合物的方法，该方法比先前已知的方法更有效。
• Investigation of the Head-Space of Roasted Meat II. Synthesis of substituted 2, 4, 5-trithia-hexanes
  作者：Paul Dubs、Rita Stüssi

  DOI：10.1002/hlca.19780610708

  日期：1978.11.1

  Substituted 2, 4, 5-trithiahexanes 1, a class of substances recently found in roasted meat, have been synthesized via two different routes.

  通过两种不同的途径合成了2、4、5-三硫代己烷1（最近在烤肉中发现的一类物质）。
• Structure - Activity Relationships for Selected Sulfur-Rich Antifungal Compounds
  作者：Felix Jakob Baerlocher、Richard Francis Langler、Mathias Ugelstad Frederiksen、Noni Mandissa Georges、Ross Davidson Witherell

  DOI：10.1071/c98141

  日期：——

  A series of sulfur compounds has been prepared and tested against two kinds of fungi: Aspergillus niger and Aspergillus flavus. Results on various sulfone disulfides and ester disulfides have led to the formulation of a proposed mechanism for fungicidal behaviour that permits one to anticipate which structures will be antifungal.

  我们制备了一系列硫化合物，并对两种真菌进行了测试。 真菌进行了测试：黑曲霉和 黄曲霉。对各种砜类 二硫化物和酯二硫化物的结果，提出了一种拟议的 的杀真菌机制。 结构将具有抗真菌作用。
• Scavenging of Radicals from the Gas Phase by Freezing with Dimethyl Disulfide
  作者：M. Schottler、K. H. Homann

  DOI：10.1002/bbpc.19870910702

  日期：1987.7

  AbstractH and O atoms and methyl radicals produced in microwave discharges of H2/He, O2/He and CH4/He mixtures, respectively, were scavenged by supersonic nozzle probing with subsequent freezing and reaction with dimethyl disulfide on a liquid nitrogen cooled wall. The main reaction products for the three kinds of radicals were CH3SH, CH3S(O)SCH3 and CH3SCH3, respectively. Side products were CH3SCH2SSCH3 and CH3SSSCH3 for H atoms and CH3S(O)2SCH3 for O atoms. – The scavenging efficiencies for the different radicals were determined and measured as a function of the gas phase radical concentration, the flow of scavenger molecules, the pressure in the vacuum chamber, and the conditions of the discharge and the flow through the sampling nozzle. It is concluded that this method is suitable for light radicals with reservations in the case of H atoms and can probably be used with still better success for heavier radicals.

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