72436-51-2

Usage

InChI:InChI=1/C13H19N/c14-13-9-5-4-8-12(13)10-11-6-2-1-3-7-11/h1-3,6-7,12-13H,4-5,8-10,14H2

Upstream product

• 53000-72-9 2-benzylcyclohexan-1-one oxime 
• 946-33-8 2-benzylcyclohexan-1-one 
• 75947-57-8 2-[hydroxy(phenyl)methyl]cyclohexylamine 
• 591-50-4 iodobenzene 
• 7003-32-9 2-METHYLCYCLOHEXYLAMINE 
• 6921-34-2 benzylmagnesium chloride 
• 286-20-4 cyclohexane-1,2-epoxide 
• 5333-61-9 trans-2-benzylcyclohexanol 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 

Downstream Products

• 105206-09-5 (E)-2-(phenylmethylene)cyclohexanamine 
• 41338-67-4 (+/-)-cis-2-acetylamino-1-benzyl-cyclohexane 

Relevant academic research and scientific papers

Access to Benzazepinones by Pd-Catalyzed Remote C-H Carbonylation of γ-Arylpropylamine Derivatives

A general method for the construction of seven-membered rings through Pd-catalyzed C(sp2)-H carbonylation at the remote ?-position of γ-arylpropylamine derivatives, including chiral α-amino acids, has been developed using Mo(CO)6 as the CO source, furnishing richly functionalized benzo[c]azepin-1-one derivatives. The readily removable N-SO2Py protecting/directing group provides high levels of chemo-, regio- and diastereoselectivity. Furthermore, this method is amenable to the postsynthetic modification of complex molecules such as small peptides.

Palladium-Catalyzed C(sp3)?H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group

C?H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C?H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C?H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ?-cyclopalladation of the arylation product is reported.

2-Amino-2-oxazolines as subtype selective α2 adrenoceptor agonists

Cyclohexylamino oxazoline I (AGN 190837), an analogue of 2 (Bay a6781), is a potent α2 adrenoceptor agonist. On the basis of a design generated by receptor-ligand modeling, a number of cyclohexyl and norbornyl analogues were synthesized wherein the propyl group of I was replaced by phenylalkyl subsituents. This resulted in compound 6 being an α(2c) selective agonist, as well as 7 and 9 being α(2a)/α(2c) selective.

2-(Phenylmethylene)cycloalkylamines and -azetidines

2-(Phenylmethylene)cycloalkylamines and -azetidines of the formula STR1 and acid addition salts thereof, e.g., 1-[2-(phenylmethylene)cyclohexyl]azetidine, and related compounds, which have analgesic, antidepressant and mixed analgesic/antidepressant central nervous system (CNS) activities, and which are useful in treating pain and/or depression in mammals including humans. The invention provides processes for preparing the compounds as well as compositions containing the compounds and methods for using the compounds as analgesic and/or antidepressant drugs for humans and valuable mammalian animals.