3-ethyl-2-(2-acetanilidovinyl)benzothiazolium iodide | 35080-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ethyl-2-(2-acetanilidovinyl)benzothiazolium iodide
• 英文别名: 2-<ω-Acetanilido-vinyl>-benzthiazol-ethoiodid；2-<ω-Acetanilido-vinyl>-benzthiazol-ethoiodid, 3-Ethyl-2-<2-(N-Acetyl-anilino)-vinyl>-benzothiazolium-iodid；2-<ω-Acetanilido-vinyl>-benzthiazol-ethoiodid, 3-Ethyl-2-(β-acetanilidovinyl)-benzthiazolium-iodid；2-ω-Acetanilinovinyl-3-aethyl-benzthiazolium-jodid；3-Aethyl-2-<2-(N-phenyl-acetamino)-vinyl>-benzothiazolium-jodid；2-<ω-Acetanilido-vinyl>-benzthiazol-ethoiodid, 3-Ethyl-2-<2-(N-phenyl-acetamido)-vinyl>-benzthiazoliumiodid；2-<2-Acetanilido-vinyl>-3-aethyl-benzothiazolium-jodid；N-[2-(3-ethyl-1,3-benzothiazol-3-ium-2-yl)ethenyl]-N-phenylacetamide;iodide
• CAS: 35080-47-8
• 化学式: C₁₉H₁₉N₂OS*I
• 分子量: 450.343
• InChiKey: MNJURKTVDAMYOT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-ethyl-2-(2-acetanilidovinyl)benzothiazolium iodide 在 tetraphosphorus decasulfide 、 三乙胺 作用下， 生成 2-Thiazolidinone,3-ethyl-5-[(3-ethyl-2(3H)-benzothiazolylidene)ethylidene]-4-thioxo-
  参考文献：
  名称：

  Nys, Ind. chim. belge Sonderband 27. Congr. int. Chim. ind. Bruessel 1954, Bd. 3, S. 635, 636

  摘要：

  DOI：
• 作为产物：
  描述：

  [(3-ethyl-3H-benzothiazol-2-yliden)-ethyliden]-aniline; hydriodide 、 乙酸酐 生成 3-ethyl-2-(2-acetanilidovinyl)benzothiazolium iodide
  参考文献：
  名称：

  Sugimoto, Kagaku Kenkyusho Hokoku, 1949, vol. 25, p. 265,271

  摘要：

  DOI：

文献信息

• Synthesis and spectral properties of malononitrile-based merocyanine dyes
  作者：A. V. Kulinich、N. A. Derevyanko、A. A. Ishchenko

  DOI：10.1007/s11172-006-0196-0

  日期：2005.12

  Di-, tetra-, and hexamethine merocyanines derived from malononitrile and heterocycles with moderate (dyes 1–6), strong (7–9), and weak (10 and 11) electron-releasing ability were synthesized. The electronic structures of merocyanines 10 and 11 are similar to the neutral polyene state, whereas those of 7–9 are similar to the ideal polymethine state. These tendencies become more pronounced with increasing length of the polymethine chain. The merocyanines derived from heterocyclic residues with weak or moderate electron-releasing ability exhibit a positive solvatochromism, whereas those with strong electron-releasing ability show a negative solvatochromism. An increase in the polarity of the solvent makes the former compounds more similar to polymethines, whereas the latter become more similar to polyenes bearing opposite charges on the end groups. The nature of the factors (nonspecific solvation, specific nucleophilic and electrophilic solvation, and vibronic interactions) responsible for the observed characteristic features was analyzed.

  合成了由美克腈和具有中等（染料1-6）、强（染料7-9）及弱（染料10和11）电子供给能力的杂环衍生的二甲、四甲和六甲美克腈。美克腈10和11的电子结构类似于中性聚烯状态，而7-9的电子结构则更接近理想的聚美烯状态。随着聚美烯链长的增加，这些趋势变得更加明显。由具有弱或中等电子供给能力的杂环残基衍生的美克腈表现出正溶剂色变，而那些具有强电子供给能力的则表现出负溶剂色变。溶剂极性的增加使得前者的化合物更类似于聚美烯，而后者则更类似于在末端基团带有相反电荷的聚烯。对导致观察到的特征特性的因素（非特异性溶剂化、特异性亲核和亲电子溶剂化以及振动耦合效应）进行了分析。
• α-Polymethine-Substituted Boron Dipyrromethenes - BODIPY-Based NIR Cyanine-Like Dyes
  作者：Mykola P. Shandura、Viktor P. Yakubovskyi、Andriy O. Gerasov、Olexiy D. Kachkovsky、Yevgen M. Poronik、Yuriy P. Kovtun

  DOI：10.1002/ejoc.201101674

  日期：2012.3

  series of dyes bearing polymethine chromophore units in boron dipyrromethene (BODIPY) α-positions were prepared by condensation of 3,5-dimethyl boron dipyrromethene with various hemicyanines. One or two methyl groups of the starting material can react, yielding the corresponding mono- and disubstituted derivatives. The deeply coloured monosubstituted dyes belong to the family of merocyanine dyes and exhibit

  通过 3,5-二甲基硼二吡咯亚甲基与各种半花青的缩合，制备了一系列在硼二吡咯亚甲基 (BODIPY) α-位上带有聚次甲基发色团单元的染料。起始材料的一个或两个甲基可以反应，产生相应的单和二取代衍生物。深色单取代染料属于部花青染料家族，表现出与介观类似物相似的光谱特性和化学行为。另一方面，与单取代染料相比，双取代染料显示出更复杂的吸收光谱，并且它们的吸收最大值发生红移（高达 970 nm，这是硼二吡咯亚甲基衍生物中已知的最红移的吸收）。光谱方法和量子化学计算表明，在改变外围发色团系统的特征时，长波长电子跃迁从二吡咯亚甲基型到聚甲炔型的演变。已经分析了最高电子跃迁的性质。
• Chxgh
  申请人：——

  公开号：US02734900A1

  公开（公告）日：1956-02-14

  The invention comprises compounds of the formula <;FORM:0774780/IV(b)/1>; or of the formula <;FORM:0774780/IV(b)/2>; wherein R is an alkyl, substituted alkyl, aralkyl or alkenyl group, R1 is a phenanthryl, naphthyl or a 2-thienyl group, R2 is a hydrogen atom or a methyl group, R3 is a hydrogen atom or an alkyl, substituted alkyl, aralkyl, phenyl or substituted phenyl or furyl group, X is an anion and Z represents the non-metallic atoms to complete a heterocylic nucleus of the thiazole, benzthiazole, naphthathiazole benzoxazole, naphthoxazole, benzselenazole napthaselenazole or thiazoline series, which nuclei may be substituted, e.g. by alkyl, aryl, thienyl, halogen, hydroxy or alkoxy atoms or groups ; it also comprises the process for the preparation of the above compounds and also the broader class of compounds of the formula I wherein R1 may be any carbocyclic aromatic group or thienyl group, wherein a compound of the formula <;FORM:0774780/IV(b)/3>; is condensed with a ketone of the formula or <;FORM:0774780/IV(b)/4>; The quaternary salt of the formula III may be formed in situ by using the free base together with a compound of the formula R-X. In the above general formul R may suitably be a saturated alkyl group of 1-4 carbon atoms or a b -hydroxyethyl, carboxymethyl, carbethoxymethyl, methoxyethyl, benzyl or allyl group ; X may suitably be a chloride, bromide, iodide, perchlorate, thiocyanate, acetate, methylsulphate, ethylsulphate, benzenesulphonate or toluenesulphonate anion ; Z may suitably be the atoms necessary to complete a thiazole, benzthiazole, naphthathiazole, benzoxazole, naphthoxazole, benzselenazole, naphthaselenazole or thiazoline ring which may be substituted for example by methyl, phenyl, chlorine, bromine, iodine, methoxy, hydroxy, methylenedioxy or ethoxy atoms or groups ; R1 may suitably be a phenyl, tolyl, chlorophenyl, hydroxyphenyl, methoxyphenyl, naphthyl, di-methylphenyl, p - dimethylaminophenyl, p - diethylaminophenyl, 9 - phenanthryl or 2 - thienyl group and R3 may suitably be a saturated alkyl group of 1-4 carbon atoms or a benzyl, phenyl, tolyl, b -methoxyphenyl or furyl group. Suitable ketones of the formul IV and V are 1-acetonaphthone, acetophenone, isophorone, methyl - 2 - thienylketone, p - dimethylamino-acetophenone, 9 - acetylphenanthnene, 3 : 5 - dimethyl - 2 - cyclohexene - 1 - one, 5 - ethyl - 3 - methyl - 2 - cyclohexene - 1 - one, 5 - furyl 3 - methyl - 2 - cyclohexene - 1 - one and 3 - methyl - 5 - phenyl - 2 - cyclohexene - 1 - one. In examples there are prepared by the above process, (1) 3 - ethyl - 2 - (2 - a - naphthylpropenyl) benzthiazolium iodide ; (2) 3-ethyl-2 - (2 - phenyl)propenyl - benzthiazolium - p - toluene sulphonate ; (3) 3 - ethyl - 2 - (1 : 5 : 5-trimethyl - 3 - cyclohexenylidene) methylbenzthiazolium iodide ; (4) 3 - ethyl - 2 - (2 - (2 - thienyl) propenyl) benzthiazolium p - toluene-sulphonate ; (5) 1-ethyl-2-(2-(2-thienyl) propenyl) naphtha [1 : 2] - thiazolium iodide ; (6) 3 - ethyl - 2 - (2 - (p - dimethylaminophenyl) propenyl) benzthiazolium iodide ; (7) 3 - ethyl-2 - [2 - (2 : 5 - dimethylphenyl) propenyl) benzthiazolium iodide ; (8) 3 - ethyl - 2 - (2 - (9 - phenanthryl) propenyl) benzthiazolium iodide ; (9) 1 - ethyl - 2 - (2 - p - hydroxyphenyl) propenyl - naphtha [1 : 2] - thiazolium iodide ; (10) 1 - methyl - 2 - (2 - (1 - naphthyl) propenyl) naphtha [1 : 2] - thiazolium iodide ; (11) 5 - chloro - 3 - ethyl - 2 - (1 : 5 : 5 - trimethyl - 3 - cyclohexenylidene) - methylbenzthiazolium p - toluene sulphonate ; (12) 3-ethyl-2-(1 : 5 : 5-trimethyl - 3 - cyclohexenylidene) - methylbenzoxazolium iodide ; (13) 3-ethyl-2-(1 : 5 : 5-trimethyl - 3 - cyclohexenylidene) methyl benzselenazolium iodide ; (14) 2-(1 : 5-dimethyl-3-cyclohexenylidene) methyl - 3 - ethyl - benzthiazolium iodide ; (15) 1-ethyl-2-(1 : 5 : 5-trimethyl - 3 - cyclohexenylidene) methyl naphtha [1 : 2] - thiazolium iodide and (16) 3-ethyl - 2 - (1 : 5 : 5 - trimethylcyclohexenylidene) methylnaphtha : [2 : 1] - thiazolium iodide. Specifications 344,409 [Group IV], 637,039, 669,174 and 774,779 [all in Group IV (c), are referred to.

  该发明涉及公式为<;FORM:0774780/IV(b)/1>;或公式为<;FORM:0774780/IV(b)/2>;的化合物，其中R是烷基，取代烷基，芳基烷基或烯基基团，R1是菲烯基，萘基或2-噻吩基团，R2是氢原子或甲基基团，R3是氢原子或烷基，取代烷基，芳基烷基，苯基或取代苯基或呋喃基团，X是阴离子，Z代表非金属原子，以完成噻唑，苯并噻唑，萘并噻唑，苯并噁唑，萘并噁唑，苯并硒唑，萘并硒唑或噻唑环的杂环核，这些核可以被取代，例如通过烷基，芳基，噻吩基，卤素，羟基或烷氧基原子或基团取代。它还包括制备上述化合物的过程，以及公式I的更广泛的化合物类，其中R1可以是任何碳环芳香基团或噻吩基团，其中公式<;FORM:0774780/IV(b)/3>;的化合物与公式或<;FORM:0774780/IV(b)/4>;的酮缩合。III式的季铵盐可以通过将自由碱与公式R-X的化合物一起使用来原位形成。在上述一般公式中，R可以适当是1-4个碳原子的饱和烷基基团或β-羟乙基，羧甲基，羧乙氧甲基，甲氧基乙基，苄基或烯丙基基团；X可以适当是氯化物，溴化物，碘化物，高氯酸盐，硫氰酸盐，乙酸盐，甲基磺酸盐，乙基磺酸盐，苯磺酸盐或甲苯磺酸盐阴离子；Z可以适当是必要的原子来完成噻唑，苯并噻唑，萘并噻唑，苯并噁唑，萘并噁唑，苯并硒唑，萘并硒唑或噻唑环，可以通过甲基，苯基，氯，溴，碘，甲氧基，羟基，亚甲二氧基或乙氧基原子或基团取代；R1可以适当是苯基，甲苯基，氯苯基，羟基苯基，甲氧基苯基，萘基，二甲基苯基，对-二甲基氨基苯基，对-二乙基氨基苯基，9-菲烯基或2-噻吩基团，R3可以适当是1-4个碳原子的饱和烷基基团或苄基，苯基，甲苯基，β-甲氧基苯基或呋喃基团。适用于公式IV和V的合适的酮包括1-乙酰基萘酮，苯乙酮，异佛农，甲基-2-噻吩酮，对-二甲基氨基苯乙酮，9-乙酰基菲并[1，2]噻唑，3:5-二甲基-2-环己烯-1-酮，5-乙基-3-甲基-2-环己烯-1-酮，5-呋喃基3-甲基-2-环己烯-1-酮和3-甲基-5-苯基-2-环己烯-1-酮。在示例中，通过上述过程制备了（1）3-乙基-2-（2-a-萘基丙烯基）苯并噻唑盐酸盐；（2）3-乙基-2-（2-苯基）丙烯基-苯并噻唑-p-甲苯磺酸盐；（3）3-乙基-2-（1:5:5-三甲基-3-环己烯基）甲基苯并噻唑盐酸盐；（4）3-乙基-2-（2-（2-噻吩）丙烯基）苯并噻唑-p-甲苯磺酸盐；（5）1-乙基-2-（2-（2-噻吩）丙烯基）萘并[1:2]-噻唑盐酸盐；（6）3-乙基-2-（2-（对-二甲基氨基苯基）丙烯基）苯并噻唑盐酸盐；（7）3-乙基-2-[2-（2:5-二甲基苯基）丙烯基）苯并噻唑盐酸盐；（8）3-乙基-2-（2-（9-菲烯基）丙烯基）苯并噻唑盐酸盐；（9）1-乙基-2-（2-对-羟基苯基）丙烯基-萘并[1：2]-噻唑盐酸盐；（10）1-甲基-2-（2-（1-萘基）丙烯基）萘并[1：2]-噻唑盐酸盐；（11）5-氯-3-乙基-2-（1:5:5-三甲基-3-环己烯基）-甲基苯并噻唑-p-甲苯磺酸盐；（12）3-乙基-2-（1:5:5-三甲基-3-环己烯基）-甲基苯并噁唑盐酸盐；（13）3-乙基-2-（1:5:5-三甲基-3-环己烯基）甲基苯并硒唑盐酸盐；（14）2-（1:5-二甲基-3-环己烯基）甲基-3-乙基-苯并噻唑盐酸盐；（15）1-乙基-2-（1:5:5-三甲基-3-环己烯基）甲基萘并[1：2]-噻唑盐酸盐和（16）3-乙基-2-（1:5:5-三甲基环己烯基）甲基萘并[2：1]-噻唑盐酸盐。规格344,409 [IV组]，637,039，669,174和774,779 [均在IV（c）组中]。
• Novel polymethine dyes and imaging compositions
  申请人：Eastman Kodak Company

  公开号：US04855213A1

  公开（公告）日：1989-08-08

  Polymethine dyes are disclosed containing an acidic electron accepting terminal nucleus comprised of an isocyano group. The dyes are useful as spectral sensitizers in ultravioilet responsive imaging compositions.

  披草聚合物染料是含有酸性电子受体末端核心的染料，该核心包括异氰基。这些染料可用作紫外响应成像组合物中的光谱增感剂。
• Photographically useful chalcogenazolylidene and chalcogenazolium dyes and methods for their preparation
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0136847A2

  公开（公告）日：1985-04-10

  Novel aromatic chalcogenazolylidene and chalcogenazolium nucleus containing dyes and methods and intermediates for their preparation are disclosed.

  本发明公开了新型芳香缩醛唑亚基和缩醛唑鎓含核染料及其制备方法和中间体。