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cis-2-Butene-1,4-diol Sale

(Synonyms: 顺式-1,2-二羟甲基乙烯) 目录号 : GC63629

cis-2-Butene-1,4-diol 是一种用于合成抗病毒药物 oxetanocin A 的化合物。cis-2-Butene-1,4-diol 是研究异构化与氢化和氢解反应的探针。

cis-2-Butene-1,4-diol Chemical Structure

Cas No.:6117-80-2

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500 mg
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产品描述

cis-2-Butene-1,4-diol, an industrial product, can be used for the synthesis of antiviral product oxetanocin A. cis-2-Butene-1,4-diol is a probe for studying isomerization versus hydrogenation and hydrogenolysis reactions[1][2].

[1]. M.G. Musolino, et al, cis-2-Butene-1,4-diol as probe for studying isomerization versus hydrogenation and hydrogenolysis reactions, Applied Catalysis A: General, Volume 243, Issue 2, 2003, Pages 333-346, ISSN 0926-860X.
[2]. Liang Y, et al. Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: a role for neighboring group participation•. J Org Chem. 2011;76(24):9962-9974.

Chemical Properties

Cas No. 6117-80-2 SDF
别名 顺式-1,2-二羟甲基乙烯
分子式 C4H8O2 分子量 88.11
溶解度 储存条件 Store at -20°C
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1 mM 11.3494 mL 56.7472 mL 113.4945 mL
5 mM 2.2699 mL 11.3494 mL 22.6989 mL
10 mM 1.1349 mL 5.6747 mL 11.3494 mL
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Research Update

Polycondensation of butenediol: synthesis of telechelic 2-butene-1,4-diol oligomers

J Am Chem Soc 2011 Oct 19;133(41):16390-3.PMID:21939269DOI:10.1021/ja207465h.

The catalytic condensation of cis-2-Butene-1,4-diol with CpRu(MQA)(C(3)H(5)) (Cp = cyclopentadienyl, MQA = 4-methoxyquinoline-2-carboxylate) generates poly(2-butenediol), an unsaturated telechelic polyether diol with molecular weights between 400 and 4600 g/mol. This Ru(IV) allyl catalyst enchains 2-butene-1,4-diol primarily as the linear trans-2-butenyl ether (92%) along with vinyl branches (8%). These telechelic oligomers are useful chain extenders and macromonomers, as demonstrated by their use in the synthesis of poly(lactide)-b-poly(butenediol)-b-poly(lactide) triblock copolymers. Model studies support a proposed mechanism involving the formation of Ru(IV) allyl intermediates from allylic alcohols and chain growth by selective nucleophilic displacement at the terminus of the Ru(IV) allyl to generate trans-2-butenyl ether linkages.

Selective reactions and adsorption geometries of a multifunctional molecule: cis-2-Butene-1,4-diol on Si(100)-2 x 1

Langmuir 2010 Jan 19;26(2):1019-23.PMID:19788286DOI:10.1021/la902570y.

The adsorption geometry of cis-2-Butene-1,4-diol (BEDO, HOCH(2)CH=CHCH(2)OH) on Si(100)-2 x 1 was studied using scanning tunneling microscopy (STM), high resolution X-ray photoemission spectroscopy (XPS), and near-edge X-ray absorption fine structure (NEXAFS) spectroscopy. Bias-voltage-dependent STM images exhibited features characteristic of two distinct BEDO adsorption geometries. One feature was a bright protrusion located on the center of a single dimer, indicating an on-top configuration. The low bias-voltage STM image clearly showed dark features indicative of the formation of Si-H bonds on adjacent dimers in the same dimer row. The other feature was a bright protrusion bridged on end between two adjacent dimers in the same dimer row, indicating an end-bridge configuration. Accompanying this feature, two dark features attributed to Si-H bonds were observed on opposite positions to the bridged protrusion. From the XPS results, the Si 2p core level spectra revealed that the dimer atoms are involved in the formation of Si-O and Si-H bonds. On the other hand, carbon K-edge NEXAFS spectra showed that the C=C bond does not participate in the adsorption reaction and remains as an unreacted group. Collectively, the experimental results indicate that the adsorption of BEDO on Si(100)-2 x 1 occurs through the formation of two Si-O bonds via nucleophilic reaction between the two OH groups of BEDO and two Si-Si dimers. Importantly, the maintenance of the C=C bond means that the C=C functional group can be utilized as a new reaction site for further surface chemical reactions.

Ruthenium-Catalyzed Dehydrogenative Functionalization of Alcohols to Pyrroles: A Comparison between Metal-Ligand Cooperative and Non-cooperative Approaches

J Org Chem 2022 Jun 3;87(11):7106-7123.PMID:35583483DOI:10.1021/acs.joc.2c00311.

Herein, we report the synthesis and characterization of two ruthenium-based pincer-type catalysts, [1]X (X = Cl, PF6) and 2, containing two different tridentate pincer ligands, 2-pyrazolyl-(1,10-phenanthroline) (L1) and 2-arylazo-(1,10-phenanthroline) (L2a/2b, L2a = 2-(phenyldiazenyl)-1,10-phenanthroline; L2b = 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline), and their application in the synthesis of substituted pyrroles via dehydrogenative alcohol functionalization reactions. In catalyst [1]X (X = Cl, PF6), the tridentate scaffold 2-pyrazolyl-(1,10-phenanthroline) (L1) is apparently redox innocent, and all the redox events occur at the metal center, and the coordinated ligands remain as spectators. In contrast, in catalysts 2a and 2b, the coordinated azo-aromatic scaffolds are highly redox-active and known to participate actively during the dehydrogenation of alcohols. A comparison between the catalytic activities of these two catalysts was made, starting from the simple dehydrogenation of alcohols to further dehydrogenative functionalization of alcohols to various substituted pyrroles to understand the advantages/disadvantages of the metal-ligand cooperative approach. Various substituted pyrroles were prepared via dehydrogenative coupling of secondary alcohols and amino alcohols, and the N-substituted pyrroles were synthesized via dehydrogenative coupling of aromatic amines with cis-2-Butene-1,4-diol and 2-butyne-1,4-diol, respectively. Several control reactions and spectroscopic experiments were performed to characterize the catalysts and establish the reaction mechanism.

Diels-alder adducts of 3,6-dibromophencyclone with symmetrical 1,4-disubstituted-cis-2-butenes: comparisons with the adduct of phencyclone and N-benzylmaleimide, and one-dimensional and two-dimensional nuclear magnetic resonance studies and ab initio structure calculations

Appl Spectrosc 2005 Mar;59(3):366-75.PMID:15901319DOI:10.1366/0003702053585408.

Hindered Diels-Alder adducts have been prepared from 3,6-dibromophencyclone, 2, with cis-1,4-diacetoxy-2-butene, 3; cis-2-Butene-1,4-diol, 4; and N-benzylmaleimide, 5. The adduct from the parent phencyclone, 1, with N-benzylmaleimide was prepared for comparison. One- and two-dimensional (1D and 2D) proton and carbon-13 NMR studies (at 7.05 tesla, ambient temperatures), including high-resolution COSY45 and HETCOR (XHCORR) chemical shift correlation spectra, were performed, allowing extensive rigorous assignments for protons and protonated carbons. Substantial anisotropic shielding was seen for the ortho protons of the N-benzyl group in the adducts of 5 with 1 or 2, with these aryl protons resonating at 6.25 ppm (CDCl3) for each adduct. The unsubstituted bridgehead phenyls of all four adducts showed slow exchange limit (SEL) 1H and 13C spectra. Greater shift dispersions for the bridge-head phenyl protons in the adducts from 5 relative to those from 3 or 4 suggested the role of the imide carbonyls for anisotropic contributions or for influences on adduct geometry. Ab initio geometry optimizations were performed at the Hartree-Fock level with the 6-31G* basis set (or the LACVP* basis set for the bromine-containing compounds) for each of the adducts. For the two adducts from benzylmaleimide, separate minima were located corresponding to conformers in which the benzyl group was directed into the adduct cavity (syn) or out of the adduct cavity (anti). Calculated energies and geometric parameters for the adducts are presented, and these suggested a significantly different structure for the dibromo diacetate adduct, in terms of general symmetry and bridgehead phenyl geometries, compared to the other adducts.

[Research on the modification of Kevlar fiber by polypropylene glycol and cis-2-Butene-1,4-diol]

Guang Pu Xue Yu Guang Pu Fen Xi 2005 Mar;25(3):402-4.PMID:16013317doi

The mechanism of the modification of Kevlar fiber by polypropylene glycol(PPG) and cis-2-butene-1, 4-diol was studied in the paper, the authors learned the esterification of toluene-2, 4-diisocyanate (TDI) onto Kevlar fiber by infrared spectrum. In the mean time, the infrared spectrograms of the productions which steadily disposed by PPG and butendiol were analysed respectively, the result showed that the intensity of the bands was reinforced at about 1700-1720 cm(-1) after the samples were steadily disposed, that is to say, the group of --NCO has been stabilized into --NHCO group, the effect of steady disposal was obvious; but the disposal effect of butendiol was apparently better than PPG's at the same condition. Finally, the authors compared the influence of different mol rates between TDI and butendiol on the productions. Based onthe consequence, excessive butendiol would prevent the Kevlar fiber from farther reaction, therefore, the mol rate between TDI and butendiol should approach 1:1.