2,2,5,5-tetraethyl-3,4-dithiahexane-1,6-dial | 51043-01-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: 2,2,5,5-tetraethyl-3,4-dithiahexane-1,6-dial
• 英文别名: ethyl-2-(1-ethyl-1-formyl-propyldisulfanyl)-butyraldehyde；2,2'-disulfanediylbis(2-ethylbutanal)；2,2'-diethyl-2,2'-disulfanediyl-bis-butyraldehyde；2,2'-Dithio-bis (2-ethyl-bu-tanal)；2-ethyl-2-(3-formylpentan-3-yldisulfanyl)butanal
• CAS: 51043-01-7
• 化学式: C₁₂H₂₂O₂S₂
• 分子量: 262.437
• InChiKey: ZPQXGWMOPHGNSC-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  320.7±27.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetraethyl-3,4-dithiahexane-1,6-dial 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 84.0h， 生成 {2-[1-ethyl-1-(1-ethyl-1-formyl-propyldisulfanyl)-propyl]-3-methoxy-4-oxo-azetidin-1-yl}-acetic acid ethyl ester
  参考文献：
  名称：

  C4-Alkylthiols with activity against Moraxella catarrhalis and Mycobacterium tuberculosis

  摘要：

  Antimicrobial resistance represents a global threat to healthcare. The ability to adequately treat infectious diseases is increasingly under siege due to the emergence of drug-resistant microorganisms. New approaches to drug development are especially needed to target organisms that exhibit broad antibiotic resistance due to expression of beta-lactamases which is the most common mechanism by which bacteria become resistant to beta-lactam antibiotics. We designed and synthesized 20 novel monocyclic beta-lactams with alkyl-and aryl-thio moieties at C4, and subsequently tested these for antibacterial activity. These compounds demonstrated intrinsic activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 6) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.030
• 作为产物：
  描述：

  4-(2-乙基丁-1-烯基)吗啉 在 二氯化二硫 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,5,5-tetraethyl-3,4-dithiahexane-1,6-dial
  参考文献：
  名称：

  Muehlstaedt,M. et al., Journal fur praktische Chemie (Leipzig 1954), 1973, vol. 315, p. 935 - 939

  摘要：

  DOI：

文献信息

• Nitrosothiol Esters of Diclofenac:  Synthesis and Pharmacological Characterization as Gastrointestinal-Sparing Prodrugs^,
  作者：Upul K. Bandarage、Liqing Chen、Xinqin Fang、David S. Garvey、Alicia Glavin、David R. Janero、L. Gordon Letts、Gregory J. Mercer、Joy K. Saha、Joseph D. Schroeder、Matthew J. Shumway、S. William Tam

  DOI：10.1021/jm000178w

  日期：2000.10.1

  irritation. All S-NO-diclofenac derivatives acted as orally bioavailable prodrugs, producing significant levels of diclofenac in plasma within 15 min after oral administration to mice. At equimolar oral doses, S-NO-diclofenac derivatives (20a-21b) displayed rat antiinflammatory and analgesic activities comparable to those of diclofenac in the carrageenan-induced paw edema test and the mouse phenylbenzoquinone-induced

  尽管其广泛使用，双氯芬酸仍具有非甾体抗炎药（NSAIDs）常见的胃肠道疾病，可通过同时服用胃肠道细胞保护剂（如一氧化氮（NO））来减轻。已合成了一系列含有亚硝基硫醇（-S-NO）部分作为NO供体官能团的新型双氯芬酸酯，并在体内对其生物利用度，药理活性和胃刺激性进行了评估。所有S-NO-双氯芬酸衍生物均作为口服生物可利用的前药，对小鼠口服后15分钟内在血浆中产生大量的双氯芬酸。在等摩尔口服剂量下，S-NO-双氯芬酸衍生物（20a-21b）在角叉菜胶诱发的爪水肿试验和小鼠苯基苯醌诱发的扭体试验中显示出与双氯芬酸相当的大鼠抗炎和镇痛活性。所有测试的S-NO-双氯芬酸衍生物（20a-21b）都是保胃的，与大鼠中等摩尔剂量的双氯芬酸引起的胃损害相比，它们引起的胃损害明显更少。双氯芬酸的亚硝基硫醇酯包含一类新的NO供体化合物，具有作为非甾体类抗炎药的治疗潜力，具有增强的胃安全性。所有测试的S-NO-双
• First Examples of Oxidizing Aldehydes to Carboxylic Acids in the Presence of a Tertiary Disulfide Functional Group: Synthesis of Novel Diacid-disulfides
  作者：Xinqin Fang、Upul K. Bandarage、Tiansheng Wang、Joseph D. Schroeder、David S. Garvey

  DOI：10.1055/s-2003-37518

  日期：——

  The disulfide functionality exists in numerous organic compounds of interest in both chemistry and biology. In view of the fact that the disulfide function is highly susceptible to further oxidation by a broad range of agents, conducting a chemoselective oxidation without further oxidizing the disulfide group poses a synthetic challenge. Disclosed herein are the first examples of such an oxidation in which a series of aldehyde disulfides (1a-e) were converted to the corresponding symmetrical carboxylic acid disulfides (2a-e), utilizing sodium chlorite as the oxidant, and dimethyl sulf­oxide as both a reaction solvent and an efficient hypochlorous acid scavenger.

  二硫官能团存在于化学和生物学领域中许多令人感兴趣的有机化合物中。鉴于二硫功能极易被多种介质进一步氧化，在不进一步氧化二硫基团的情况下进行化学选择性氧化是一项合成挑战。本文公开了此类氧化的首个实例，利用亚氯酸钠作为氧化剂，二甲亚砜作为反应溶剂和有效的次氯酸清除剂，将一系列醛二硫化物（1a-e）转化为相应的对称羧酸二硫化物（2a-e）。
• Muehlstaedt, Manfred; Meinhold, Hansjuergen; Martinetz, Dieter, Journal fur praktische Chemie (Leipzig 1954), 1982, vol. 324, # 4, p. 631 - 638
  作者：Muehlstaedt, Manfred、Meinhold, Hansjuergen、Martinetz, Dieter、Neumann, Eberhard

  DOI：——

  日期：——
• Enantioselective Organocatalytic Oxidation of Functionalized Sterically Hindered Disulfides
  作者：Noureddine Khiar、Siham Mallouk、Victoria Valdivia、Khalid Bougrin、Mohammed Soufiaoui、Inmaculada Fernández

  DOI：10.1021/ol070056z

  日期：2007.3.1

  The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm vanadium catalyst in terms of chemical yield and enantioselectivity. Whereas the latter system afforded mostly racemic thiosulfinates in low to moderate yields, the former one afforded thiosulfinates with up to 96% ee.
• Transannular cyclizations of 1,2-dithia-5,8-diazacyclodeca-4,8-dienes during borohydride reduction
  作者：Alummoottil V. Joshua、John R. Scott、Sham M. Sondhi、Richard G. Ball、J. William Lown

  DOI：10.1021/jo00388a020

  日期：1987.6