3-乙基-5-[(3-乙基-(3H)-苯并恶唑-2-亚基)亚乙基]-2-硫酮噻唑烷-4-酮 | 25962-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑啉
• 中文名称: 3-乙基-5-[(3-乙基-(3H)-苯并恶唑-2-亚基)亚乙基]-2-硫酮噻唑烷-4-酮
• 英文名称: 3-ethyl-5-[2-(3-ethyl-3H-benzooxazol-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one
• 英文别名: 3-ethyl-5-[(3-ethyl-3H-benzoxazol-2-yliden)-ethylidene]-2-thioxo-thiazolidin-4-one；3-Aethyl-5-[(3-aethyl-3H-benzoxazol-2-yliden)-aethyliden]-2-thioxo-thiazolidin-4-on；3-ethyl-5-[(3-ethyl-(3H)-benzoxazol-2-ylidene)ethylidene]-2-thioxothiazolidin-4-one；3-Ethyl-5-[2-(3-ethyl-1,3-benzoxazol-2-ylidene)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 25962-05-4
• 化学式: C₁₆H₁₆N₂O₂S₂
• 分子量: 332.447
• InChiKey: YAORVROFPFPJJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-乙基-5-[(3-乙基-(3H)-苯并恶唑-2-亚基)亚乙基]-2-硫酮噻唑烷-4-酮 在 alkyl- 作用下， 生成 {3-ethyl-5-[(3-ethyl-3H-benzoxazol-2-yliden)-ethyliden]-4-oxo-4,5-dihydro-thiazol-2-yl}-(1,3,3-trimethyl-3H-indol-2-yl)-methinium ; iodide
  参考文献：
  名称：

  930.有机化合物的颜色。第七部分 复杂的花青和花青

  摘要：

  DOI：

  10.1039/jr9520004762
• 作为产物：
  描述：

  3-乙基-2-硫代-4-噻唑烷二酮 、 2-[2-(乙酰基苯基氨基)乙烯基]-3-乙基苯并恶唑鎓碘化物 在 乙醇 、 三乙胺 作用下， 生成 3-乙基-5-[(3-乙基-(3H)-苯并恶唑-2-亚基)亚乙基]-2-硫酮噻唑烷-4-酮
  参考文献：
  名称：

  Studies in the Cyanine Dye Series. XI.¹ The Merocyanines

  摘要：

  DOI：

  10.1021/ja01155a095

文献信息

• Rhodanine compounds
  申请人：EASTMAN KODAK CO

  公开号：US02743278A1

  公开（公告）日：1956-04-24

  Compounds of the general formula: <;FORM:0753648/IV(a)/1>; wherein R is methyl or alkoxy and R1 is alkyl, substituted alkyl or alkenyl are prepared by heating together a compound of the general formula CH3.CO.CO.R with a compound of the general formula: <;FORM:0753648/IV(a)/2>; in the presence of zinc chloride under substantially anhydrous conditions. 5-(Butan-3-on-2-ylidene) - 3 - carbethoxyethyl - 2 - thiothiazolid-4-one is prepared by heating together 3-carbethoxymethylrhodanine, diacetyl, powdered anhydrous zinc chloride, and dioxane. 5-(Butan - 3 - on - 2 - ylidene) - 3 - carboxymethyl-2 - thiothiazolid - 4 - one, 5 - (Butan - 3 - on - 2-ylidene) - 3 - carbo n - butoxymethyl - 2 - thiothiazolid-4-one, methyl a -(3-carbomethoxymethyl-4 - keto - 2 - thiothiazolid - 5 - ylidene) - propionate, ethyl a -(3-carbethoxymethyl-4-keto-2-thiothiazolid - 5 - ylidene) - propionate, n - butyl a -(3 - carbo - n - butoxymethyl - 4 - keto - 2 - thiothiazolid - 5 - ylidene) - propionate, and methyl a - (3 - ethyl - 4 - keto - 2 - thiothiazolid - 5 - ylidene)-propionate are similarly prepared.ALSO:Merocyanine dyes of the general formula I <;FORM:0753648/IV(c)/1>; wherein R is methyl or alkoxy, R1 and R2 are alkyl, substituted alkyl or alkenyl, n and d each are 0 and 1, and Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus containing from 5 to 6 atoms in the heterocyclic ring, are prepared by condensing compounds of the general formula II <;FORM:0753648/IV(c)/2>; wherein X represents an acid radical and D an alkylthio, arylthio, or b -aminovinyl (e.g. b -acylarylaminovinyl) group, with compounds of the general formula III <;FORM:0753648/IV(c)/3>; e.g. with heating and in the presence of a diluent and a strongly basic condensing agent. 3-Carbethoxymethyl - 5 - [1 - (3 - ethylbenzthiazolin - 2 - ylidene) - hex - 2 - en - 5 - on - 4 - ylidene] - 2 - thiothiazolid -4- one is prepared by heating together 2-b -acetanilidovinylbenzthiazole ethiodide, 5-(butan - 3 - on - 2 - ylidene)-3-carbethoxyethyl - 2 - thiothiazolid - 4 - one, ethanol, and thiethylamine 3 - Carbethoxymethyl - 5 - [1 - 3 - ethylbenzthiazolin - 2 - ylidene) - butan - 3 - on - 2 - ylidene] - 2 - thiothiazo - lid - 4 - one, 3 - carbethoxymethyl - 5 - [1-(3 - methylthiazolidin - 2 - ylidene) - butan - 3 - on - 2 - ylidene] - 2 - thiothiazolid - 4 - one, and 3-carbomethoxymethyl - 5 - [1-carbomethoxy - 2 - (3-methylthiazolidin - 2 - ylidene) - ethylidene] - 2 - thiothiazolid - 4 - one are similarly prepared. Merocyanine dyes of the general formula IV <;FORM:0753648/IV(c)/4>; wherein L represents a substituted or unsubstituted methine group and R6 an alkyl, substituted alkyl or alkenyl group are prepared by condensing a compound of the general formula V <;FORM:0753648/IV(c)/5>; wherein R7 is alkyl and X, an acid radical, with compounds of the general formula III. Compounds of the general formula V are prepared by heating together with an alkyl ester R7-X1 compounds of the general formula <;FORM:0753648/IV(c)/6>; 2 - [2 - (3 - Carbethoxymethyl - 4 - keto - 2 - thiothiazolidin - 5 - ylidene) - butan - 3 - on - 1 - ylidene] - 3 - ethyl - 5 - (3 - ethylbenzoxazolin - 2 - ylidene - ethylidene) - thiazolid - 4 - one is prepared by fusing together 3 - ethyl - 5 - (3 - ethylbenzoxazolin - 2 - ylidene - ethylidene) - 2 - thiothiazolid - 4 - one and methyl p-toluenesulphonate, adding 5-(butan - 3 - on - 2 - ylidene) - 3 - carbethoxy ethyl - 2 - thiothiazolid - 4 - one, ethanol and triethylamine, and refluxing. 3 - Allyl - 2 - [2 - (3 - carbethoxymethyl - 4 - keto - 2 - thiothiazolidin - 5 - ylidene) - butan - 3 - on - 1 - ylidene] - 5 - [1 - (3 - ethylbenzthiazolin-2 - ylidene) - but - 2 - ylidene] - thiazolid - 4 - one is similarly prepared.

  通用公式化合物：其中R为甲基或烷氧基，R1为烷基，取代烷基或烯基，通过在基本无水条件下加热通用公式CH3.CO.CO.R的化合物与通用公式的化合物在锌氯化物存在下加热制备：在一起加热3-羧乙氧基甲基罗丹宁，二乙酰，粉末无水氯化锌和二氧六环。 5-（丁酮-3-酮-2-基）-3-羧乙氧基-2-噻唑烷-4-酮通过加热3-羧乙氧基甲基罗丹宁，二乙酰，粉末无水氯化锌和二氧六环一起加热制备。 5-（丁酮-3-酮-2-基）-3-羧甲基-2-噻唑烷-4-酮，5-（丁酮-3-酮-2-基）-3-羧基-丁氧基甲基-2-噻唑烷-4-酮，甲基a-（3-羧甲氧基甲基-4-酮-2-噻唑烷-5-基）-丙酸酯，乙基a-（3-羧乙氧基甲基-4-酮-2-噻唑烷-5-基）-丙酸酯，n-丁基a-（3-羧基-丁氧基甲基-4-酮-2-噻唑烷-5-基）-丙酸酯和甲基a-（3-乙基-4-酮-2-噻唑烷-5-基）-丙酸酯同样制备。另外：通用公式I的梅洛氰染料；其中R为甲基或烷氧基，R1和R2为烷基，取代烷基或烯基，n和d各为0和1，Z代表非金属原子，必要时完成含有5至6个原子的杂环核的杂环核，通过将通用公式II的化合物与通用公式III的化合物缩合制备；其中X代表酸基团，D代表烷硫基，芳基硫基或b-氨基乙烯基（例如b-酰基芳基氨基乙烯基）基团，与加热和存在稀释剂和强碱性缩合剂的情况下制备。 3-羧乙氧基甲基-5-[1-(3-乙基苯并噻唑啉-2-基)-己-2-烯-5-酮-4-基]-2-噻唑烷-4-酮通过将2-乙酰基苯并噻唑乙碘化物，5-（丁酮-3-酮-2-基）-3-羧乙氧基-2-噻唑烷-4-酮，乙醇和硫乙胺一起加热制备。 3-羧乙氧基甲基-5-[1-(3-甲基噻唑啉-2-基)-丁酮-3-酮-2-基]-2-噻唑烷-4-酮和3-羧甲氧基甲基-5-[1-羧甲氧基-2-(3-甲基噻唑啉-2-基)-乙烯基]-2-噻唑烷-4-酮同样制备。通用公式IV的梅洛氰染料；其中L代表取代或未取代的亚甲基基团，R6代表烷基，取代烷基或烯基团，通过将通用公式V的化合物与通用公式III的化合物缩合制备；其中R7为烷基，X为酸基团。通用公式V的化合物通过与烷基酯R7-X1的化合物一起加热制备。 3-烯丙基-2-[2-(3-羧乙氧基甲基-4-酮-2-噻唑啉-5-基)-丁酮-3-酮-1-基]-3-乙基-5-(3-乙基苯并噻唑啉-2-基-乙烯基)-噻唑-4-酮通过将3-乙基-5-(3-乙基苯并噻唑啉-2-基-乙烯基)-2-噻唑烷-4-酮和对甲苯磺酸甲酯熔合，加入5-（丁酮-3-酮-2-基）-3-羧乙氧基-2-噻唑烷-4-酮，乙醇和三乙胺，然后回流制备。 3-烯丙基-2-[2-(3-羧乙氧基甲基-4-酮-2-噻唑啉-5-基)-丁酮-3-酮-1-基]-5-[1-(3-乙基苯并噻唑啉-2-基)-丁-2-基]-噻唑-4-酮同样制备。
• Sytnik,Z.P. et al., Journal of general chemistry of the USSR, 1965, vol. 35, p. 645 - 650
  作者：Sytnik,Z.P. et al.

  DOI：——

  日期：——
• Investigations in the field of polymerocyanines
  作者：L. T. Bogolyubskaya、M. S. Lyubich、V. A. Bogolyubskii、Z. P. Sytnik、N. V. Kudryavskaya、R. V. Timofeeva

  DOI：10.1007/bf00478081

  日期：——
• Studies in the Cyanine Dye Series. XI.¹ The Merocyanines
  作者：L. G. S. Brooker、G. H. Keyes、R. H. Sprague、R. H. VanDyke、E. VanLare、G. VanZandt、F. L. White

  DOI：10.1021/ja01155a095

  日期：1951.11
• Polymethine dyes
  申请人：EASTMAN KODAK CO

  公开号：US02454629A1

  公开（公告）日：1948-11-23