4-ethyl-3-oxobis[1,2]dithiolo[3,4:4',3'-e][1,4]thiazine-5-thione | 188535-15-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-ethyl-3-oxobis[1,2]dithiolo[3,4:4',3'-e][1,4]thiazine-5-thione
• 英文别名: 4-Ethyl-3-oxo-3H,4H,5H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-5-thione；4-ethylbis[1,2]dithiolo[3,4-b:4′,3′-e][1,4]thiazin-3-oxo-5-thione；4-ethyl-5-thioxo-3H,4H,5H-bis([1,2]dithiolo)-[3,4-b:4',3'-e][1,4]-thiazin-3-one；4-ethyl-5-thioxo-4,5-dihydro-3H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazin-3-one；(C6S5N)SOEt；8-Ethyl-10-sulfanylidene-2,4,5,11,12-pentathia-8-azatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-dien-6-one
• CAS: 188535-15-1
• 化学式: C₈H₅NOS₆
• 分子量: 323.53
• InChiKey: QXMPBUYKBUOHGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  179
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N,N-二异丙基乙胺 在 二氯化二硫 、 环戊-1-烯-1-乙酸 作用下， 以 四氢呋喃 为溶剂， 以0.45 g的产率得到4-ethyl-3-oxobis[1,2]dithiolo[3,4:4',3'-e][1,4]thiazine-5-thione
  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 of 6,7-Dihydropyrrolo[2,1-<i>c</i> ][1,3]thiazino[3,2-<i>a</i> ]pyrazine-4(11b<i>H</i> )-(thi)ones from 1,2-Dithiolo-3-(thi)ones
  作者：Vladimir A. Ogurtsov、Yury V. Karpychev、Yulia V. Nelyubina、Petr V. Primakov、Panayiotis A. Koutentis、Oleg A. Rakitin

  DOI：10.1002/ejoc.201900142

  日期：2019.7.14

  Both monocyclic and fused 1,2‐di‐thiolo‐3‐(thi)ones underwent addition of 3,4‐dihydropyrrolo[1,2‐a]pyrazine with selective extrusion of S2 atom and formation of 6,7‐dihydropyrrolo[2,1‐c][1,3]thi‐azino[3,2‐a]pyrazine‐4(11bH)‐(thi)ones. 1,2‐Dithiolo‐3‐one moiety was found more reactive than the corresponding 1,2‐dithiole‐3‐thione one.

  单环和稠合的1,2-二硫代3-（thi）酮都加入了3,4-二氢吡咯并[1,2- a ]吡嗪，并选择性挤出了S2原子并形成了6,7-二氢吡咯并[2] ，1‐ c ] [1,3]噻嗪[3,2‐ a ]吡嗪‐4（11b H）‐（噻吩）酮。发现1,2-二硫代-3-酮比相应的1,2-二硫代-3-硫酮具有更高的反应活性。
• 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 [1,3]Dithiole and Spiro[1,3]dithiole Thiopyran Derivatives of the [1,2]Dithiolo[1,4]thiazine Ring System
  作者：Susana Barriga、Pedro Fuertes、Carlos F. Marcos、Oleg A. Rakitin、Tomás Torroba

  DOI：10.1021/jo020015a

  日期：2002.9.1

  polysulfur-nitrogen heterocycles by cycloaddition reactions to readily available tricyclic condensed 1,2-dithiole-3-thiones. Thus, treatment of bis[1,2]dithiolopyrrole ketothione 1 with diacyl acetylenes gave the bis-aducts 2a-d. On the other hand, cycloaddition of bis[1,2]dithiolo[1,4]thiazine ketothione 3 with 1 equiv of acyl or diacyl acetylenes gave [1,3]dithiolylidenyl[1,2]dithiolo[1,4]thiazines 4a-f in fair

  我们报告了通过环加成反应可容易获得的三环缩合的1,2-二硫代3-硫酮的一些新的多硫-氮杂环的合成。因此，用二酰基乙炔处理双[1,2]二硫代吡咯酮酮噻酮1，得到双加合物2a-d。另一方面，双[1,2]二硫代[1,4]噻嗪酮噻酮3与1当量的酰基或二酰基乙炔的环加成反应得到[1,3]二硫代烯基[1,2]二硫代[1,4]噻嗪4a -f中等至高产。在反应中使用三氟甲磺酸催化反应，表明反应活性较低。用2当量的DBA处理3，得到双加合物5a，并且4c与DMAD的反应得到混合的双加合物5b。