118-12-7Relevant articles and documents
A NEW METHOD OF SYNTHESIS OF CONJUGATED SYSTEMS WITH TRIS(FLUOROMETHINE) CHAIN
Pazenok, S. V.,Kovtyukh, I. P.,Yagupolskii, L. M.
, p. 4595 - 4598 (1991)
The interaction of compounds having the active methylene group with perflouroallyliodide leads to the formation of conjugated systems with the tris(fluoromethine) chain.
Crystal and solution structures of photochromic spirobenzothiopyran. First full characterization of the meta-stable colored species
Hirano, Masafumi,Osakada, Kohtaro,Nohira, Hiroyuki,Miyashita, Akira
, p. 533 - 540 (2002)
Full elucidation for stable, colorless, and meta-stable colored structures of a new spirobenzothiopyran has been achieved both in the solid state and in a solution. 1′,3′,3′-Trimethyl-6-nitrospiro[(2H)-1-benzothiopyran-2, 2′-indoline] with an ester group as a substituent at the 8-position of 1-sp shows photochromism. The blue-green colored species resulted from UV irradiation (365 nm) in one minute and spontaneously bleaches within one minute in acetone and methanol at 27 °C. UV exposure (365 nm) of 1-sp in methanol for 3 h at room temperature results in the growth of deep blue needlelike single crystals of the open form of spirobenzothiopyran, photomerocyanine 1-pmc, whose structures in the solid state and in solution were obtained unambiguously. The X-ray structural analysis of 1-pmc revealed the molecular structure of the zwitterionic photomerocyanine with s-trans,s-trans conformation. 1-pmc is soluble to polar solvents and thermally returns to 1-sp. In the DMSO solution, 1-pmc is found to return slowly to 1-sp (1-pmc gave only 18% of 1-sp for 30 min at 22 °C). The detailed NMR studies in DMSO-d6 including COSY and NOE techniques as well as isotope labeling of the compound showed the structure with s-trans,s-cis conformation in a solution.
Structures of Lithium Salts of 2,3,3-Trimethylindolenine and Its 5-Methoxy Derivative in Solution and the Solid State
Jackman, L. M.,Scarmoutzos, L. M.,Smith, B. D.,Williard, Paul G.
, p. 6058 - 6063 (1988)
An X-ray crystal structure of lithium 2,3,3-trimethylindolenide etherate shows it to be a disolvated dimer having a η3-azaallyl-type structure.The structures of the salt in several solvents have been established by studies of 13C chemical shifts, 6Li, 15N spin-spin splitting, 7Li quadrupole splitting constants, and apparent degrees of aggregation determined by vapor pressure barometry.It is the η3-azaallyl dimer disolvate in diethyl ether, a tetrasolvated dimer in dioxolane, a mixture of monomer splitting constants of 230, 156, 180 - 190 (0.27 - 0.75 M), and 217 kHz, respectively.In diethyl ether with 4 equiv of hexamethylphosphoric triamide, the salt is a mixture of monomeric and triple ion species.Lithium 5-methoxy-2,3,3-trimethylindolenide forms similar species except that, in tetrahydrofuran, the tendency for dimer formation is enhanced, which leads to a higher proportion of C- to N-methylation in its reaction with methyl chloride in that solvent.
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Bernauer et al.
, p. 717,723 (1960)
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Method for preparing indoline
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Paragraph 0016; 0018; 0019; 0021; 0024, (2021/01/12)
The invention relates to a method for preparing indoline. The metho is characterized by comprising the following steps of: a, performing condensation and cyclization on phenylhydrazine hydrochloride or substituted phenylhydrazine hydrochloride and a methyl ketone compound in a solvent under a non-catalytic condition to generate C2-methylindole or a derivative thereof, and conducting cooling, salting-out, suction filtration and desolventizing successively; b, subjecting the condensation ring-closing product C2-methylindole or the derivative thereof to reacting with chloromethane under the conditions of pressurization, solvent presence and catalysis to generate corresponding quaternary ammonium salt or quaternary ammonium salt containing substituent groups; and c, dissolving the salt generated in the step b in water, then carrying out alkaline hydrolysis in a solvent and alkali liquor, and successively performing layering, desolvation and distillation to obtain a product, namely 1,3,3-trimethyl-2-methyleneindoline or a derivative thereof. The whole technological process is simple, the amount of three wastes is small, the cost is low, the yield is high, and the method is a green technology suitable for industrial amplification and outstanding in economic benefit.
Method for preparing indoline polymethin dye via one-pot method
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Paragraph 0075; 0077; 0094; 0095; 0097, (2019/01/14)
The invention discloses a method for preparing an indoline polymethin dye via a one-pot method. The method comprises the following steps of: carrying out condensation and ring closing on phenylhydrazine or para-substituted phenylhydrazine hydrochloride and methyl isopropyl ketone in an alcohol solvent under the catalysis of sulfuric acid so as to generate 2,3,3-trimethylindole or a derivative thereof, adding alkali to carry out neutralization, and carrying out filtration to remove salt; adding an appropriate acid-binding agent in the filtrate, dropwise adding dimethyl sulfate to generate 1,3,3-trimethyl-2--methylene indoline or a derivative thereof; and directly adding 1-phenyl-3-methyl-4-formyl-5-pyrazolone, and carrying out acid catalysis and condensation to generate a target dye. The method has the advantages of being easy to operate, high in yield, low in cost and less in wastewater.