10409-47-9

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 19980-35-9 1-trimethylsilyloxy-2-methyl-1-cyclohexene 
• 110-91-8 morpholine 
• 128-08-5 N-Bromosuccinimide 

Downstream Products

• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 66432-76-6 dimethyl 2-methyladipate 
• 99249-35-1 2-methyl-2-cyclohexen-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 99249-46-4 (2S,3S)-2,3-Bis-benzyloxymethyl-6-bromo-6-methyl-1,4-dioxa-spiro[4.5]decane 
• 3128-07-2 6-oxoheptanoic acid 
• 96304-02-8 2-hydroxy-2-methylcyclohexanone 
• 54322-98-4 2-(α-hydroxybenzyl)-2-methylcyclohexanone (erythro) 
• 54322-99-5 2-(α-hydroxybenzyl)-2-methylcyclohexanone (threo) 
• 89237-27-4 1-phenylazo-2-methyl-cyclohexene 
• 111016-60-5 3-Hydroxy-2-methyl-cyclohex-1-enecarbaldehyde 
• 111016-59-2 1-[2-(1,3-dithianyl)]-2-methyl-2-cyclohexen-1-ol 
• 194937-78-5 3-[1,3]dithian-2-yl-2-methyl-cyclohex-2-enol 
• 194937-79-6 Formic acid 3-[1,3]dithian-2-yl-2-methyl-cyclohex-2-enyl ester 
• 99249-36-2 1-methyl-2-norcaranone cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 

Relevant academic research and scientific papers

A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate

Cyclic ketones reacted with N-bromosuccinimide (NBS) catalysed by NH 4OAc in Et2O at 25°C to give the corresponding α-brominated ketones in good yields, while acyclic ketones were efficiently brominated in CCl4 at 80°C.

A New and Highly Effectiwe Aldol Synthesis

A new approach has been demonstrated for the regiospecific aldol synthesis by the simultaneous addition of α-halo carbonyl derivatives and aldehydes or ketones to a suspension of diethylaluminium chloride and zinc in tetrahydrofuran at low temperature.This technique is also employable under mild conditions for the Reformatsky reaction to give β-hydroxy esters in excellent yield.One of the unique synthetic applications of this process is illustrated by the intramolecular cyclization of α-bromo esters of ω-hydroxy aldehyde,which produces macrolides, an important cla ss of compounds in the antibiotic field.

Total Synthesis and Structure Revision of Halioxepine

The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

Cobalt-Catalyzed Regioselective Olefin Isomerization under Kinetic Control

Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin isomerization reaction. By taking the advantage of fine-tunable NNP-pincer ligand structures, this catalytic system features high kinetic control of regioselectivity. This mild catalytic system enables the isomerization of 1,1-disubstituted olefins bearing a wide range of functional groups in excellent yields and regioselectivity. The synthetic utility of this transformation was highlighted by the highly selective preparation of a key intermediate for the total synthesis of minfiensine. Moreover, a new strategy was developed to realize the selective monoisomerization of 1-alkenes to 2-alkenes dictated by installing substituents on the γ-position of the double bonds. Mechanistic studies supported that the in situ generated Co-H species underwent migratory insertion of double bond/β-H elimination sequence to afford the isomerization product. The less hindered olefin products were always preferred in this cobalt-catalyzed olefin isomerization due to an effective ligand control of the regioselectivity for the β-H elimination step.

COMPOUNDS THAT INHIBIT MCL-1 PROTEIN

Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.

Intramolecular carbonickelation of alkenes

The efficiency of the intramolecular carbonickelation of substituted allylic ethers and amines has been studied to evaluate the influence of the groups borne by the double bond on this cyclization. The results show that when this reaction takes place, it affords only the 5-exo-trig cyclization products, viz. dihydrobenzofurans or indoles. Depending on the tethered heteroatom (O or N), the outcome of the cyclization differs. While allylic ethers are relatively poor substrates that undergo a side elimination and need an intracyclic double bond to proceed, allylic amines react well and afford indoline and indole derivatives. Finally, the synthesis of the trinuclear ACE core of a morphine-like skeleton was achieved by using NiBr2bipy catalysis.

Cu(OTf)2-catalyzed α-halogenation of ketones with 1,3-dichloro-5,5'-dimethylhydantoin and N-bromosuccinimide

Copper(II) triflate catalyses efficiently the α-halogentaion of aryl or alkyl ketones with l.3-diehloro-5.5'-dimethylhydantoin and N-bromosuccinimde to give the corresponding α,α-dichloroketones and α-bromoketones in high yield with excellent product selectivity.

Facile synthesis of c/s-2-alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols

Silyl triflate-promoted rearrangement of c/s-2,3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then sllylatlon, afforded good yields (～70-75%) of the c/s-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituents, e.g., terf-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism.

Halogenation of carbonyl compounds by an ionic liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)

An ionic liquid, acetylmethylimidazolium halide ([AcMIm]X), in combination with ceric ammonium nitrate promotes halogenations of a wide variety of ketones and 1,3-keto esters at the ?-position. The ionic liquid acts here as reagent as well as reaction medium, and thus the reaction does not require any organic solvent or conventional halogenating agent. The reaction is completely arrested when the radical quencher TEMPO is used. A plausible radical mechanism is also suggested. CSIRO 2007.

Rapid and catalyst-free α-halogenation of ketones using N-halosuccinamides in DMSO

α-Halogenation of various carbonyl compounds such as β-keto-esters, cyclic ketones, and lactams with N-halosuccinamides (NBS, NCS, NIS) in the presence of DMSO proceeded very smoothly to give the corresponding α-monohalogenated products in good to excellent yields with high selectivity under catalyst-free conditions. Copyright Taylor & Francis Group, LLC.