23519-90-6Relevant articles and documents
Amino acid-bearing ROMP polymers with a stereoregular backbone
Lee, Jae Chul,Parker, Kathlyn A.,Sampson, Nicole S.
, p. 4578 - 4579 (2006)
The ruthenium-catalyzed ring-opening polymerization (ROMP) of 1-cyclobutenecarbonyl glycine methyl ester provides translationally invariant, head-to-tail ordered polymers. This polybutadiene backbone contains (within the limits of detection) only E-trisub
Scope of the ring-opening metathesis polymerization (ROMP) reaction of 1-substituted cyclobutenes
Song, Airong,Lee, Jae Chul,Parker, Kathlyn A.,Sampson, Nicole S.
, p. 10513 - 10520 (2010)
The reactivities of a series of 1-substituted cyclobutene derivatives (carboxylate esters, carboxamides, and carbinol esters) were investigated as substrates for ring-opening metathesis polymerization (ROMP) with [(H 2IMes)(3-Br-pyridine)2(Cl)2Ru=CHPh]. Both the secondary amides of 1-cyclobutenecarboxylic acid and the esters of 1-cyclobutene-1-methanol undergo polymerization. The secondary amides provide translationally invariant polymers (E-olefins). Although the carbinol esters yield stereo- and regiochemically heterogeneous polymers, the 1-cyclobutenecarboxylic acid esters and tertiary amides undergo ring-opening metathesis (ROM) but not ROMP. The regio- and stereochemical outcomes of these ROMP and ROM reactions were analyzed at the B3LYP/6-31G* and LANL2DZ levels of theory. Calculations suggest that the regiochemistry and stereochemistry of the addition to the propagating carbene to form the metallocyclobutane intermediate depend on both charge distribution and steric interactions.
Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
Gouverneur, Véronique,Hell, Sandrine M.,Laudadio, Gabriele,Meyer, Claudio F.,Misale, Antonio,No?l, Timothy,Trabanco, Andrés A.,Willis, Michael C.
supporting information, p. 720 - 725 (2020/02/20)
Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
SULFONYLCYCLOALKYL CARBOXAMIDE COMPOUNDS AS TRPA1 MODULATORS
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Paragraph 0165; 0166; 0167; 0171; 0172; 0173, (2018/02/28)
The invention is concerned with the compounds of formula (I): and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.
Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: A dramatic ligand effect on the diastereoselectivity
Chen, Ya-Jing,Hu, Tian-Jiao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 8773 - 8776 (2015/05/20)
A highly diastereo- and enantioselective rhodium-catalyzed arylation of cyclobutenes for the efficient synthesis of chiral cyclobutanes has been developed. Chiral diene ligands exhibited excellent capability for the reaction diastereoselectivity control.
NOVEL COMPOUNDS
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Page/Page column 59, (2015/12/17)
Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate
Jung, Michael E.,Deng, Gang
, p. 11002 - 11005 (2013/02/22)
Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.
ALTERNATING RING-OPENING METATHESIS POLYMERIZATION
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, (2011/09/20)
The invention relates to the field of polymers and olefin polymerization, and more specifically olefin metathesis polymerization. The invention provides regioregular alternating polymers and methods of synthesizing such polymers.
Accelerated ring-opening metathesis polymerization of a secondary amide of 1-cyclobutene by hydrogen-bonding interaction
Lee, Kil Sun,Choi, Tae-Lim
scheme or table, p. 3908 - 3911 (2011/10/03)
A hydrogen-bond-assisted model is proposed for ring-opening metathesis polymerization (ROMP) of a secondary amide of 1-cyclobutene, resulting in the fastest reaction rate in a nonpolar solvent, toluene. This new model was supported by the investigation on
STEREOREGULAR ROMP POLYMERS
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Page/Page column 19; 20, (2010/11/30)
The invention relates to stereoregular ROMP polymers, the monomers used to make them, and the processes used to convert the monomers to the polymers. The monomer has formula (1) : wherein: X = [(CY12)b - CY2sub
