58987-23-8

Upstream product

• 100-66-3 methoxybenzene 
• 23860-35-7 cyclohexylacetic acid chloride 
• 5292-21-7 Cyclohexylacetic acid 
• 637-69-4 4-Methoxystyrene 
• 110-82-7 cyclohexane 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 108-93-0 cyclohexanol 
• 139488-44-1 mercapto-1-(4’-methoxyphenyl)ethanone 
• 110-83-8 cyclohexene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 99-91-2 para-chloroacetophenone 
• 87508-67-6 (1R,6R,7R)-7-(4-Methoxy-phenyl)-bicyclo[4.2.0]octan-7-ol 
• 87482-81-3 (1S,6S,7R)-7-(4-Methoxy-phenyl)-bicyclo[4.2.0]octan-7-ol 
• 110-83-8 cyclohexene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 104151-24-8 N-1-(4-methoxyphenyl)-2-cyclohexylethylformamide 
• 71666-43-8 2-cyclohexyl-1-(4-hydroxy-phenyl)-ethanone 
• 412051-28-6 2-cyclohexyl-1-(4-triisopropylsilyloxy-phenyl)-ethanone 
• 412051-33-3 2-bromo-2-cyclohexyl-1-(4-triisopropylsilanyloxy-phenyl)-ethanone 
• 412051-72-0 2-(5-benzyloxy-2-hydroxy-phenylsulfanyl)-2-cyclohexyl-1-(4-triisopropylsilanyloxy-phenyl)-ethanone 
• 104151-25-9 N-1-(4-methoxyphenyl)-2-cyclohexylethylacetamide 
• 104151-27-1 1,2-dibromo-1-(3-bromo-4-methoxyphenyl)-cyclohexylethene 
• 104151-26-0 trans-1-methoxy-4-(2-cyclohexylethenyl)benzene 

Relevant academic research and scientific papers

Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.

Ruthenium-Catalyzed α-Alkylation of Ketones Using Secondary Alcohols to β-Disubstituted Ketones

An assortment of aromatic ketones was successfully functionalized with a variety of unactivated secondary alcohols that serve as alkylating agents, providing β-disubstituted ketone products in good to excellent yields. Remarkably, challenging substrates such as simple acetophenone derivatives are effectively alkylated under this ruthenium catalysis. The substituted cyclohexanol compounds displayed product-induced diastereoselectivity. Mechanistic studies indicate the involvement of the hydrogen-borrowing pathway in these alkylation reactions. Notably, this selective and catalytic C-C bond-forming reaction requires only a minimal load of catalyst and base and produces H2O as the only byproduct, making this protocol attractive and environmentally benign.

Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols

We report herein the development of a S atom transfer process using triethyl phosphite as the S atom acceptor that allows thiols to serve as precursors of C-centered radicals. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups readily participate in this reductive coupling. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.

A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes

An intermolecular reductive C-C coupling of electrophilic alkyl radicals and alkenes has been developed. Thiols were used as both hydrogen-donating reagents and alkyl radical precursors in the presence of triethyl phosphite and radical initiator. A wide range of alkenes, including styrenes, and aliphatic olefins were well tolerated in this transformation. Mechanistic studies indicated that a phosphite promoted radical desulfurization of thiols to access electrophilic alkyl radicals and a radical chain propagation process may be involved in this transformation.

Catalytic Cross-Coupling of Secondary Alcohols

Herein, an unprecedented ruthenium(II) catalyzed direct cross-coupling of two different secondary alcohols to β-disubstituted ketones is reported. Cyclic, acylic, symmetrical, and unsymmetrical secondary alcohols are selectively coupled with aromatic benzylic secondary alcohols to provide ketone products. A single catalyst oxidizes both secondary alcohols to provide selectively β-disubstituted ketones to broaden the scope of this catalytic protocol. Number of bond activation and bond formation reactions occur in selective sequence via amine-amide metal-ligand cooperation operative in Ru-MACHO catalyst. The product-induced diastereoselectivity was also observed. Kinetic and deuterium labeling experiments suggested that the aliphatic secondary alcohols undergo oxidation reaction faster than benzylic secondary alcohols, selectively assimilating to provide the cross-coupled products. Reactions are sensitive to steric hindrance. This new C-C bond forming methodology requires low catalyst load and catalytic amount of base. Notably, the reaction produces H2 and H2O as the only byproducts making the protocol greener, atom economical and environmentally benign.

Ruthenium-Catalyzed Direct Cross-Coupling of Secondary Alcohols to β-Disubstituted Ketones

The β-disubstituted ketone functionality is prevalent in biologically active compounds and in pharmaceuticals. A ruthenium-catalyzed direct synthesis of β-disubstituted ketones by cross-coupling of two different secondary alcohols is reported. This new protocol was applied to the synthesis of variety of β-disubstituted ketones from various cyclic, acyclic, symmetrical, and unsymmetrical secondary alcohols. An amine-amide metal-ligand cooperation in a Ru catalyst facilitates the activation and formation of covalent bonds in selective sequences to provide the products. Kinetic and deuterium-labeling experiments suggested that aliphatic alcohols oxidize faster than benzylic secondary alcohols. A plausible mechanism is proposed on the basis of mechanistic and kinetic studies. Water and H 2 are the only byproducts from this selective cross-coupling of secondary alcohols. 1 Introduction 2 Catalytic Self-or Cross-Coupling of Alcohols and Selectivity Challenges 3 Recent Developments in the Synthesis of β-Disubstituted Ketones 4 Scope of Ruthenium-Catalyzed Cross-Couplings of Secondary Alcohols 5 Mechanistic Studies and Proposed Mechanism 6 Conclusion.

Inert naphthenic hydrocarbon C(sp3)-H bond functionalization method

The invention belongs to the field of organic synthesis, and particularly relates to an inert naphthenic hydrocarbon C(sp3)-H bond functionalization method. The method comprises the following steps: adding substituted styrene as shown in Formula Ia, catalyst ferrous chloride, oxidizer and alkali into a dry reaction bulb; adding naphthenic hydrocarbon as shown in Formula IIa; putting the reaction bulb under a condition of 100-120 DEG C, and reacting for 12-24 hours; and after the reaction is completed, filtering the reaction solution through glass dropper containing silica gel, flushing with ethyl acetate, performing spin-drying on the filtrate, and separating through column chromatography to obtain a target product as shown in Formula I. The reaction formula is shown in the specification.

In(III)-mediated chemoselective dehydrogenative interaction of ClMe 2SiH with carboxylic acids: Direct chemo- And regioselective friedel-crafts acylation of aromatic ethers

Chemoselective dehydrogenative interaction of ClMe2SiH with a carboxylic acid group in the presence of InX3 is reported. 13C NMR investigation revealed the formation of PhCOOSi(Cl)Me 2as the major transient intermediate. Chemo- and regioselective Friedel-Crafts acylation of aromatic ethers directly from carboxylic acids was established.

Estrogen receptor modulators

The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.

Reaction of some N-acyl-1-alkylamines with polyphosphoric ester PPE: nuclear magnetic resonance and stereochemistry of reaction products

Phenylindanes were obtained from the reaction of N-acyl-1-arylalkylamines with polyphosphoric ester (PPE). cis-1-Methyl-3-(3,4-dimethoxyphenyl)-5,6-dimethoxyindane was synthesized to determine which stereoisomer was produced by N-formyl and N-acetyl-1-(3,4-dimethoxyphenyl)ethylamine with PPE.Nuclear magnetic resonance specta (1H and 13C) of several mono-, 1,3-di-, and 1,2,3-tri-substituted indanes were fully analyzed to provide information on steric interactions and conformation of the cyclopentene ring.Possible cyclodimerization pathways are proposed.