14310-34-0Relevant articles and documents
2,2'-Dimethoxybibenzyl
Ross, Jennifer-Nicola,Wardell, James,Ferguson, George,Low, John N.
, p. 976 - 977 (1994)
The 2,2'-dimethoxybibenzyl molecule, C16H18O2, has the midpoint of the -CH2-CH2- bond on an inversion centre.Each benzene ring deviates slightly from planarity, shows marked angular distortion and is inclined at 81.5(1) deg to the plane of the C(Ar)-CH2-CH2-moiety.
Ni-Catalyzed Iterative Alkyl Transfer from Nitrogen Enabled by the in Situ Methylation of Tertiary Amines
Nwachukwu, Chideraa Iheanyi,McFadden, Timothy Patrick,Roberts, Andrew George
, p. 9979 - 9992 (2020/09/03)
Current methods to achieve transition-metal-catalyzed alkyl carbon-nitrogen (C-N) bond cleavage require the preformation of ammonium, pyridinium, or sulfonamide derivatives from the corresponding alkyl amines. These activated substrates permit C-N bond cleavage, and their resultant intermediates can be intercepted to affect carbon-carbon bond-forming transforms. Here, we report the combination of in situ amine methylation and Ni-catalyzed benzalkyl C-N bond cleavage under reductive conditions. This method permits iterative alkyl group transfer from tertiary amines and demonstrates a deaminative strategy for the construction of Csp3-Csp3 bonds. We demonstrate PO(OMe)3 (trimethylphosphate) to be a Ni-compatible methylation reagent for the in situ conversion of trialkyl amines into tetraalkylammonium salts. Single, double, and triple benzalkyl group transfers can all be achieved from the appropriately substituted tertiary amines. Transformations developed herein proceed via recurring events: The in situ methylation of tertiary amines by PO(OMe)3, Ni-catalyzed C-N bond cleavage, and concurrent Csp3-Csp3 bond formation.
A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism
Ochoa, Cristian,Solinski, Amy E.,Nowlan, Marcus,Dekarske, Madeline M.,Wuest, William M.,Kozlowski, Marisa C.
, p. 74 - 79 (2019/11/20)
Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.