767-13-5Relevant articles and documents
Preparation method of cis, cis-3, 5-dimethyl-1-cyclohexanol
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, (2020/08/18)
The invention belongs to the field of chemistry, and discloses a synthesis method of a cis, cis-3, 5-dimethyl-1-cyclohexanol compound shown as a formula (I). Acetaldehyde and ethyl acetoacetate are used as raw materials, and cis, cis-3, 5-dimethyl-1-cyclohexanol is synthesized by a series of reactions such as knoevenagel condensation, hydrolysis, decarboxylation, hydrogenation reduction, reduction, acylating chlorination, hydrolysis and the like. The raw materials and auxiliary materials of the route are simple and easily available, the reaction conditions are mild, the operation is simple andconvenient, the synthesis cost is low, and the obtained product has high chiral purity (the product/isomer ratio is 30: 1-100: 1) and is suitable for large-scale production.
Cerium-free Luche reduction directed by rehydrated alumina
Jones-Mensah, Ebenezer,Nickerson, Leslie A.,Deobald, Jackson L.,Knox, Hailey J.,Ertel, Alyssa B.,Magolan, Jakob
, p. 3748 - 3753 (2016/06/06)
A 1,2-regioselective reduction of α,β-unsaturated ketones to their corresponding allylic alcohols is accomplished with NaBH4 in the presence of acidic activated alumina rehydrated to the Brockmann II grade by adding 3 % w/w water. The substrate scope includes eight ketones reduced in high regio- and diastereoselectivity to their corresponding allylic alcohols. This is the first example of the strategy of systematically tuning the surface chemistry of alumina via partial rehydration in order to modulate selectivity in a reaction. Alumina is an appealing alternative to the common Luche reduction additive, CeCl3, from the perspective of cost and procedural simplicity.
Transfer Hydrogenation of Ketones with (1-) as the Precatalyst
Bhaduri, Sumit,Sharma, Krishna,Mukesh, Doble
, p. 1191 - 1200 (2007/10/02)
The cluster 1a has been found to be an efficient precatalyst for the transfer hydrogenations of ketones and α,β-unsaturated ketones.With substrates such as (5S)-carvone , (3R)-methylcyclopentanone and (3R)-methylcyclohexanone, moderate to high diastereoselectivities were observed for reduction of the conjugated olefinic and ketonic functionalities respectively.Aromatisation of carvone to 5-isopropyl-2-methylphenol and disproportionation of cyclohex-2-en-1-one to phenol and cyclohexanone have also been found to be catalysed by 1a.Studies with radical inhibitors and other evidence suggest a radical mechanism for the transfer-hydrogenation and aromatisation reactions.In the transfer hydrogenation of cyclohex-2-en-1-one, the rate of conversion of 1a into other soluble species can be modelled accurately if autocatalysis is assumed.The time-dependent concentration profiles of cyclohex-2-en-1-one, cyclohexanone and cyclohexanol are simulated well if autocatalytic formation of an active intermediate followed by consecutive reactions leading to the formation of products is assumed.Such a model is also consistent with the proposed radical mechanism.
