4-ethylbis[1,2]dithiolo[3,4-b:4′,3′-e][1,4]thiazin-3,5-dithione | 188535-13-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-ethylbis[1,2]dithiolo[3,4-b:4′,3′-e][1,4]thiazin-3,5-dithione
• 英文别名: 4-ethyl-3H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5(4H)-dithione；4-ethylbis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5-dithione；4H-Bis(1,2-dithiole[3,4-b:4,3-E])[1,4]-thiazine-3,5-dithione, 4-ethyl-；8-ethyl-2,4,5,11,12-pentathia-8-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-diene-6,10-dithione
• CAS: 188535-13-9
• 化学式: C₈H₅NS₇
• 分子量: 339.596
• InChiKey: RCWAGLKJZYEJAS-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C (decomp)
• 沸点：
  436.8±55.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  194
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-ethylbis[1,2]dithiolo[3,4-b:4′,3′-e][1,4]thiazin-3,5-dithione 在 三乙胺 、 氯代肟基乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到4-Ethylbis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5(4H)-dione
  参考文献：
  名称：

  From Hünig's Base to Bis([1,2]dithiolo)-[1,4]thiazines in One Pot: The Fast Route to Highly Sulfurated Heterocycles

  摘要：

  DOI：

  10.1002/anie.199702811
• 作为产物：
  描述：

  4-ethyl-3-oxobis[1,2]dithiolo[3,4:4',3'-e][1,4]thiazine-5-thione 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以70%的产率得到4-ethylbis[1,2]dithiolo[3,4-b:4′,3′-e][1,4]thiazin-3,5-dithione
  参考文献：
  名称：

  Selective Syntheses of Bis[1,2]dithiolo[1,4]thiazines and Bis[1,2]dithiolopyrroles from Hünig's Base

  摘要：

  The reaction of N,N-diisopropylethylamine (Hunig's base) and disulfur dichloride in 1,2-dichloroethane, in the presence of DABCO, gives 4-ethylbis[1,2]dithiolo[5,4-b][4',5'-e][1,4]thiazinine-3,5-dithione (1), or, by addition of oxygen donors, the 3-oxo-5-thione 2 or 3,5-dione 3 derivatives are selectively obtained. When the first reaction is performed in boiling chlorobenzene, 4-ethylbis[1,2]dithiolo[4,5-b][5',4'-d]pyrrole-3,5-dithione (4) is obtained by sulfur extrusion from 1, and in the presence of oxygen donors, the 3-oxo-5-thione 5 or 3,5-dione 6 derivatives are selectively obtained. Some interconversions of compounds 1-6 are described, and a coherent set of reaction pathways for the formation of all six products is proposed. X-ray diffraction shows that the new bis-dithiolothiazine ring system of 1-3 is folded out-of planarity about the thiazine N-S vector, with the N-ethyl group folded back over the thiazine ring in a scorpion-like conformation. The new bis-dithiolopyrrole ring system of 4-6 is planar and extensively delocalized.

  DOI：

  10.1021/jo971864e

文献信息

• Synthesis and thermal stability of imino-1,3-dithietanes. Influence of structural factors
  作者：V. A. Ogurtsov、Yu. V. Karpychev、P. A. Belyakov、Yu. V. Nelyubina、K. A. Lyssenko、O. A. Rakitin

  DOI：10.1007/s11172-010-0028-0

  日期：2009.2

  The reaction of 1,2-dithiol-3-thiones with isonitriles at room temperature affords imino-1,3-dithietanes. The reaction is reversible. According to 1H NMR spectroscopy, the rise of the temperature shifts the equilibrium to the starting compounds. The structure of one of the imino-1,3-dithietanes was established by X-ray diffraction.

  在室温下，1,2-二硫醇-3-硫酮与异氰酸酯反应生成亚胺-1,3-二硫杂环丁烷。该反应是可逆的。根据氢核磁共振（¹H NMR）波谱分析，温度的升高使平衡向起始化合物方向偏移。其中一种亚胺-1,3-二硫杂环丁烷的结构通过X射线衍射确定。
• Transformations of N-ethylamines into amide derivatives under the action of sulfur monochloride
  作者：L. S. Konstantinova、A. A. Berezin、O. A. Rakitin

  DOI：10.1007/s11172-007-0179-9

  日期：2007.6

  Tertiary N-ethylamines were converted into amide derivatives by reactions with sulfur monochloride and DABCO at 0 °C. Depending on the nature of the substituents in the amine, the reaction can be accompanied by unexpected transformations.

  通过在 0 °C 下与一氯化硫和 DABCO 反应，将叔 N-乙胺转化为酰胺衍生物。根据胺中取代基的性质，该反应可能伴随着意想不到的转变。
• Synthesis of bis[1,2]dithiolo[1,4]thiazine imines from Hünig's base
  作者：Stanislav A. Amelichev、Susana Barriga、Lidia S. Konstantinova、Tatjana B. Markova、Oleg A. Rakitin、Charles W. Rees、Tomás Torroba

  DOI：10.1039/b105243h

  日期：——

  N-Ethyldiisopropylamine, S2Cl2 and DABCO in chloroform at room temperature form intermediate salts which react with nucleophiles to give tricyclic bis[1,2]dithiolo[1,4]thiazine derivatives. The reactions of some representative amino compounds as the nucleophiles are now described. With arenesulfonamides 1a,b and their N,N-dichloro derivatives 2a,b, the N,N′-bis(arylsulfonyl)dithiolothiazinediimines 3a,b are formed in modest yields. With toluene-p-sulfonohydrazide and aniline the more complex reactions give only the monohydrazone 7 and the bicyclic anilino derivative 8, respectively, in very low yields. The diimines 3a,b are also produced, in better yield, from the bis(1,2-dithiole-3-thione) 4 with chloramine B and T; similarly the analogous monothione 12 gives the monoimines 13a,b. The reaction rates and yields (up to 93%) in the conversion of 12 to 13 are greatly increased by scandium triflate. Possible reaction mechanisms are considered.

  N-乙基二异丙胺、二氯化硫（S2Cl2）和DABCO在室温下在氯仿中形成中间盐，这些中间盐与亲核试剂反应，生成三环双[1,2]二硫杂噻嗪衍生物。现在描述一些代表性氨基化合物作为亲核试剂的反应。与芳基磺酸酰胺1a、b及其N,N-二氯衍生物2a、b反应，产生N,N′-双（芳基磺酰）二硫噻嗪双亚胺3a、b，收率适中。与对苯磺酰肼和苯胺的反应较复杂，仅分别生成单肼素7和双环苯胺衍生物8，收率非常低。从双（1,2-二噻唑-3-硫酮）4与氯胺B和T反应时，二亚胺3a、b也以更好的收率生成；类似地，类似的单硫酮12生成单亚胺13a、b。12转化为13的反应速率和收率（高达93%）在三氟化钪的作用下大大提高。考虑了可能的反应机制。
• Synthesis of Highly Branched Sulfur−Nitrogen Heterocycles by Cascade Cycloadditions of [1,2]Dithiolo[1,4]thiazines and [1,2]Dithiolopyrroles
  作者：Susana Barriga、Pedro Fuertes、Carlos F. Marcos、Tomás Torroba

  DOI：10.1021/jo035748p

  日期：2004.5.1

  same dipolarophiles gave the 1:2, 1:3, or 1:4 adducts 5a−c, 6a, 7a, 8a, 9a, and 10a,c,d selectively in fair to high yields. Reaction conditions were crucial for achievement of selectivity in thermal reactions. Catalysis by scandium triflate was used in the reaction of 4a and 2 equiv of DMAD. Treatment of the [1,2]dithiolo[1,4]thiazine dithione 11 with DBA gave the 1:2, 1:3 (two isomers), and 1:4 adducts

  我们报告了通过级联环加成到容易获得的多环1,2-二硫代3-硫酮上的一些新的多硫-氮杂环的合成。因此，用乙炔二羧酸二甲酯（DMAD）或二苯甲酰基乙炔（DBA）处理双[1,2]二硫代吡咯并二硫酮1，得到1：4加合物2a，b和3a。另一方面，双[1,2]二硫代[1,4]噻嗪二硫酮4a - d与相同的双亲性化合物环加成后，可得到1：2、1：3或1：4加合物5a - c，6a，7a，8a，9a和10a，c，d有选择地以中等至高产。反应条件对于实现热反应的选择性至关重要。三氟甲磺酸scan的催化用于4a和2当量的DMAD的反应。的[1,2] dithiolo [1,4]噻嗪二硫酮治疗11具有DBA得到1：2,1：3（两种异构体），和1：4分的加合物12 - 14和15A - d选择性。所选实施例的循环伏安法显示出不可逆过程，不受与杂环系统键合的外围基团的影响。
• Synthesis of Pyrrolidine-Fused 1,3-Dithiolane Oligomers by the Cycloaddition of Polycyclic Dithiolethiones to Maleimides and Evaluation as Mercury(II) Indicators
  作者：Pedro Fuertes、María García-Valverde、José V. Cuevas、Borja Díaz de Greñu、Teresa Rodríguez、Josefa Rojo、Tomás Torroba

  DOI：10.1021/jo500076c

  日期：2014.3.7

  The scandium triflate-catalyzed cycloaddition reaction of polycyclic 1,2-dithiolethiones to maleimides is described. The reaction constitutes an easy approach to linear as well as branched oligomeric cis-fused dihydro[1,3]dithiolo[4,5-c]pyrrole-4,6-dione rings interconnected by 3,5-diylidenethiomorpholine-2,6-dithione or ylidene-6-thioxo[1,2]dithiolo[3,4-b][1,4]thiazin-3-one groups. The presence of

  描述了三氟甲磺酸scan催化的多环1，2-二硫代硫酮与马来酰亚胺的环加成反应。该反应构成了由3,5-二亚甲基硫代吗啉-2,6-相互连接的直链和支链低聚顺式稠合二氢[1,3]二硫代[4,5 - c ]吡咯-4,6-二酮环的简便方法二硫酮或亚烷基-6-硫代[1,2]二硫代[3,4- b ] [1,4]噻嗪-3-一个基团。结构中存在高度着色，高度极化的推挽式α，β-不饱和硫酮基使这些化合物对有机或混合有机/水溶剂中汞（II）阳离子的存在敏感。