22362-59-0

Upstream product

• 109-72-8 n-butyllithium 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 592-41-6 1-hexene 
• 89-95-2 2-methyl-benzyl alcohol 
• 90-02-8 salicylaldehyde 
• 108-95-2 phenol 
• 592-42-7 1,5-Hexadien 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 3634-67-1 trihexylsilyl chloride 
• 19311-91-2 N,N-diethylsalicylamide 
• 611-20-1 salicylonitrile 
• 111-25-1 1-bromo-hexane 
• 2528-61-2 Heptanoic acid chloride 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 17404-56-7 2-(1-Hexylheptyl)-phenol 
• 17508-92-8 4,6-Dinitro-2-(1-hexylheptyl)-phenol 
• 1247949-43-4 2-(1-iminoheptyl)phenol 
• 17403-81-5 2-((E)-1-Hexyl-hept-1-enyl)-phenol 

Relevant academic research and scientific papers

Asymmetric Rh-catalyzed intermolecular hydroacylation of 1,5-hexadiene with salicylaldehyde

Asymmetric intermolecular hydroacylation between salicylaldehyde (1) and 1,5-hexadiene (2) using a combination of [RhCl(C8H14) 2]2 (0.10 eq), (S)-BINAP (0.10 eq), and ZnBr2 (0.20 eq) afforded an enant

Relay Catalysis by Achiral Borane and Chiral Phosphoric Acid in the Metal-Free Asymmetric Hydrogenation of Chromones

A strategy of relay catalysis by achiral borane and chiral phosphoric acid was successfully developed for the asymmetric hydrogenation of chromones, giving the desired products in high yields with up to 95% ee. Achiral borane and chiral phosphoric acid are highly compatible in this reaction. The achiral borane acts as a Lewis acid for the first-step hydrogenation, and the chiral phosphoric acid acts as an effective chiral proton shuttle to control the enantioselectivity.

THIOSEMICARBAZONES INHIBITORS OF LYSOPHOSPHATIDIC ACID ACYLTRANSFERASE AND USES THEREOF

Lysophosphatidic acid acyltransferase-beta (LPAAT-β) catalyzes the production of phosphatidic acid (PA) from lysophosphatidic acid (LPA). The lipid cofactor PA contributes to the activation of c-Raf, BRAF, mTOR and PKC-ζ. LPAAT-β expression is a prognostic factor in gynecologic malignancies and is being investigated as a therapeutic target in a variety of tumor types. A class of thiosemicarbazones was identified as inhibitors of LPAAT-β from a screen of a library of small molecules. A focused library of thiosemicarbazones derivatives was prepared and led to the development of compounds which potently inhibit LPAAT-β and inhibit the growth of MiaPaCa2 human pancreatic cancer cells.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Nitrile-promoted Rh-catalyzed intermolecular hydroacylation of olefins with salicylaldehyde

Rh-catalyzed intermolecular hydroacylation between salicylaldehyde and alkenylnitriles proceeded at room temperature to preferentially give normal-hydroacylated products. Addition of CH3CN and NaOAc accelerated the Rh-catalyzed hydroacylation of monoolefins to exclusively produce the normal-hydroacylated products under mild reaction conditions. Plausible mechanisms for the regioselections are also described.

Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation between Salicylaldehydes and 1,4-Penta- or 1,5-Hexadienes

Intermolecular hydroacylation between salicylaldehydes 1, 26-40 and 1,4-penta- or 1,5-hexadienes 4-13 by Rh-catalyst proceeded under mild reaction conditions to give a mixture of iso- and normal-hydroacylated products 14-25, 41-55, and 57-60. In the hydroacylation reaction, chelation of both salicylaldehyde and diene to the Rh-complex plays a crucial role. The ratio of iso- and normal-hydroacylated products could be regulated by the addition of salicylic acid or amines. The effects of various Rh-complexes, solvents, and additives were examined, and the plausible mechanisms of the catalytic cycle were proposed on the basis of the deuterium-labeling salicylaldehyde experiments.

Double-chelation-assisted Rh-catalyzed intermolecular hydroacylation

(Matrix presented) Rh-Catalyzed intermolecular hydroacylation between salicylaldehydes and 1,5-hexadienes proceeded under remarkably mild reaction conditions to afford a mixture of iso- and normal-hydroacylated products in good yields. The experiments using deuterated salicylaldehyde-d revealed that "double chelation" of salicylaldehyde and 1,5-hexadiene to Rh-complex played vital roles in the catalytic cycle of intermolecular hydroacylation.

Novel ring-opening reaction of chromanone oxime

A novel ring-opening reaction of chromanone and its oxime with n-butyl lithium is reported.

The Effect of Carbonyl Containing Groups in the Terminal Chains on Mesomorphic Properties in Aromatic Esters and Thioesters. I. α-Keto Groups on the Phenolic End

The effect of inserting a ketone group in the α-position of the alkyl chain on the phenolic end of 4,4'-disubstituted phenylbenzoates and di-(4'-substituted phenyl)-trans-cyclohexane-1,4-dicarboxylates on mesomorphic properties as compared to those properties observed for the corresponding alkyl compounds was determined.Transition tempetatures were higher and mesophase ranges usually wider in the α-keto compounds in both series.Nematic phases were observed in both series, but a strong preference for a single smectic phase predominated with this being a smectic A phase in the phenylbenzoates and a smectic C phase in the cyclohexane diesters.A variety of crystal changes and a few complex melting transition were also observed in the cyclohexane diesters. - Keywords: liquid crystals; x-ray; phenylbenzoates; phase transistors; trans-cyclohexane-1,4-dicarboxylates.