106-96-7Relevant articles and documents
Kinetics of the reaction of N,N-dimethylaniline with 1-bromoalk-2-ynes
Andreev,Ryzhakov,Sobolev
, p. 1486 - 1489 (2017)
Quaternization of N,N-dimethylaniline with propargyl bromide, 1-bromobut-2-yne, and 1-bromooct-2-yne were studied. It was shown that, with the lengthening chain of the substituent at the triple bond, the quaternization rate tends to increase.
Trimethylhalosilane elimination from trimethylsilylsubstituted gem-dihalocyclopropanes
Seyferth, Dietmar,Jula, Theodore F.
, p. 109 - 114 (1968)
The aluminum halide-catalyzed elimination of trimethylhalosilane from 1,1-dihalo-2-(trimethylsilyl)cyclopropanes (XCl and Br) resulted in the formation of propargyl halides, HCCCH2X. Reaction of 1,1-dichloro-2,2-dimethyl-3-(trimethylsilyl) cyclopropane with sodium ethoxide in ethanol also resulted in elimination of trimethylchlorosilane; the organic product was 3-ethoxy-3-methyl-1-butyne, HCCCMe2OEt, and a mechanism involving β-elimination of trimethylchlorosilane to give 1-chloro-3,3-dimethylcyclopropene and reaction of the latter to produce the acetylenic ether is suggested.
Anti-AIDS agents. Part 62: Anti-HIV activity of 2′-substituted 4-methyl-3′,4′-di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs
Zhang, Qian,Chen, Ying,Xia, Peng,Xia, Yi,Yang, Zheng-Yu,Yu, Donglei,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
, p. 5855 - 5857 (2004)
Four 4-methyl-3′,4′-di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs (7a-d) with different alkyl substituents at the 2′-position were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 2′-Methyl-2′-ethyl-4-methyl DCK (7b) was more potent (EC50 = 0.22 μM, TI > 175) than the other three compounds (7a, 7c, and 7d), but significantly less potent than 4-methyl DCK (2, EC50 = 0.0059 μM, TI > 6600). Four 4-methyl-3′,4′- di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs (7a-d) with different alkyl substituents at the 2′-position were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 2′-Methyl-2′-ethyl-4-methyl DCK (7b) was more potent (EC 50 = 0.22 μM, TI > 175) than the other three compounds (7a, 7c, and 7d), but significantly less potent than 4-methyl DCK (2, EC50 = 0.0059 μM, TI > 6600). The bioassay results indicated that the 2′-substituents had a strong effect on the anti-HIV activity, and gem-dimethyl substitution at the 2′-position was greatly preferable to larger alkyl substituents or hydrogen atoms.
Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method
Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.
supporting information, p. 4176 - 4182 (2021/02/01)
Daptomycin (DAP) is a calcium (Ca2+)-dependent FDA-approved antibiotic drug for the treatment of Gram-positive infections. It possesses a complex pharmacophore hampering derivatization and/or synthesis of analogues. To mimic the Ca2+-binding effect, we used a chemoenzymatic approach to modify the tryptophan (Trp) residue of DAP and synthesize kinetically characterized and structurally elucidated regiospecific Trp-modified DAP analogues. We demonstrated that the modified DAPs are several times more active than the parent molecule against antibiotic-susceptible and antibiotic-resistant Gram-positive bacteria. Strikingly, and in contrast to the parent molecule, the DAP derivatives do not rely on calcium or any additional elements for activity.
An Additive-Free, Base-Catalyzed Protodesilylation of Organosilanes
Yao, Wubing,Li, Rongrong,Jiang, Huajiang,Han, Deman
, p. 2250 - 2255 (2018/02/23)
We report an additive-free, base-catalyzed C-, N-, O-, and S-Si bond cleavage of various organosilanes in mild conditions. The novel catalyst system exhibits high efficiency and good functional group compatibility, providing the corresponding products in good to excellent yields with low catalyst loadings. Overall, this transition-metal-free process may offer a convenient and general alternative to current employing excess bases, strong acids, or metal-catalyzed systems for the protodesilylation of organosilanes.
Palladium-catalyzed cyclization of alkynoic acids to form vinyl dioxanones bearing a quaternary allylic carbon
Ogiwara, Yohei,Sato, Kazuya,Sakai, Norio
supporting information, p. 5296 - 5299 (2017/11/06)
A palladium-catalyzed intramolecular reaction of carboxylic acids and alkynes in a novel cyclization manner was developed. This unique cyclization efficiently provided a wide range of complex ring systems-vinyl dioxanones bearing a quaternary allylic carbon. Mechanistic studies suggest an allenyl carboxylate as an intermediate.
Ruthenium bipyridyl tethered porous organosilica: A versatile, durable and reusable heterogeneous photocatalyst
Jana, Avijit,Mondal, John,Borah, Parijat,Mondal, Sujan,Bhaumik, Asim,Zhao, Yanli
supporting information, p. 10746 - 10749 (2015/06/30)
A versatile heterogeneous photocatalysis protocol was developed by using ruthenium bipyridyl tethered porous organosilica (Ru-POS). The versatility of the Ru-POS catalyst in organo-photocatalysis was explored by (i) oxidative aromatization of Hantzsch ester, (ii) reductive dehalogenation of alkyl halides, and (iii) functional group interconversion (FGI) of alcohols to alkyl halides. This journal is
MANUFACTURING OF STABILIZED PROPARGYL BROMIDE
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Page/Page column 12; 13, (2014/04/04)
This invention provides a process for obtaining propargyl bromide in high yield from propargyl alcohol and phosphorus bromide, in the form of a stable composition with alkylbromide.
Iron-catalyzed synthesis of functionalized 2H-chromenes via intramolecular alkyne-carbonyl metathesis
Bera, Krishnendu,Sarkar, Soumen,Biswas, Srijit,Maiti, Sukhendu,Jana, Umasish
experimental part, p. 3539 - 3544 (2011/06/23)
An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, bromo, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.
Asymmetric synthesis of α-allenylglycines
Bucuroaia, Carmen,Groth, Ulrich,Huhn, Thomas,Klinge, Michael
experimental part, p. 3605 - 3612 (2009/12/01)
The coupling of the homocuprate of the bislactim ether of cyclo-(-L-Val-Gly-) (9) with primary propargyl halides produces the allenyl-substituted bislactim ethers 11 in a highly diastereoselective manner, whereas the alkylation of the lith-iated bislactim ether of cyclo-(-L-Val-Gly-) yields the proparg-yl-substituted bislactim ethers 12. Subsequent hydrolysis affords, after protection of the amino group, the methyl α- allenylglycinates 15, the α-allenylglycines 16, and the methyl α-propargylglycinates 17.
