107020-80-4

Basic information

• Product Name: N-Acetyl-DL-cyclohexylglycine
• Synonyms: N-Acetyl-DL-cyclohexylglycine;2-AcetaMido-2-cyclohexylacetic acid
• CAS NO: 107020-80-4
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• Mol File: 107020-80-4.mol

Chemical Properties

• Boiling Point: 428.641 °C at 760 mmHg
• Flash Point: 213.035 °C
• Appearance: /
• Density: 1.134 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N-Acetyl-DL-cyclohexylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-DL-cyclohexylglycine(107020-80-4)
• EPA Substance Registry System: N-Acetyl-DL-cyclohexylglycine(107020-80-4)

Safety Data

• Hazardous Substances Data: 107020-80-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
N-Acetyl-DL-cyclohexylglycine is used as a chiral building block for the synthesis of pharmaceutical compounds, leveraging its unique structural properties to create new drugs for various medical conditions.
Used in Organic Synthesis:
In the field of organic synthesis, N-Acetyl-DL-cyclohexylglycine is utilized as a chiral ligand, playing a crucial role in homogeneous catalysis, particularly in asymmetric hydrogenation reactions, to produce enantiomerically pure compounds.
Used in Health and Wellness Research:
Due to its demonstrated antioxidant properties, N-Acetyl-DL-cyclohexylglycine is used in research aimed at understanding its potential benefits in health and wellness applications, exploring its capacity to contribute to the development of novel treatments and preventative measures.

InChI:InChI=1/C10H17NO3/c1-7(12)11-9(10(13)14)8-5-3-2-4-6-8/h8-9H,2-6H2,1H3,(H,11,12)(H,13,14)

Upstream product

• 5664-29-9 2-cyclohexylglycine 
• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 75-05-8 acetonitrile 

Downstream Products

• 14001-39-9 N-(cyclohexylidenemethyl)acetamide 
• 14328-67-7 N-Tosyl-S-benzyl-cysteinyl-tyrosyl-(2-cyclohexyl-2-amino-essigsaeuremethylester) 
• 145618-11-7 (S)-amino(cyclohexyl)acetic acid methyl ester 
• 14328-51-9 (2S)-amino(cyclohexyl)ethanoic acid 

Relevant articles and documents

First amidocarbonylation with nitriles for the synthesis of N-acyl amino acids

A new and efficient one-pot synthesis of N-acyl-α-amino acids by amidocarbonylation is described. Starting from aldehydes, nitriles and carbon monoxide in the presence of acid and palladium catalysts the desired N-acyl amino acids are obtained in good yie

Syngas reactions XIV. Amidocarbonylation as a route to α-amidocarboxylic acids

The amidocarbonylation of olefin and aldehyde substrates has been applied to the synthesis of a variety of amidocarboxylic acids, including surface active agents (e.g.C14-C16 N-acyl-α-amino acids), specialty surfactants (such as the sarcosinates), intermediates for sweeteners (e.g. aspartame), food additives (e.g. glutamic acid), and certain chelating agents.Homogeneous cobalt and rhodium-based catalysts, modified, for example, with sulfoxide and bidentate phosphine ligands, have been tailored to the synthesis of each individual class of product.Process studies, including examinations of reaction rate, product selectivity, as well as catalyst stability, have been undertaken for N-acetylglycine and amido acid surfactant syntheses.

A study of amidocarbonylation reactions catalyzed by Pd/HZSM-5

A HZSM-5-supported palladium catalyst, which was prepared by the conventional impregnation method, was utilized in amidocarbonylation reactions. Several important parameters were optimized to give moderate to excellent yields. The catalyst recycling of Pd/HZSM-5, for the first time, was achieved for at least four run times without depreciation of catalytic activity. The studies of TEM images revealed that agglomeration of the palladium species of Pd/ HZSM-5 catalyst was avoided after reaction, which was quite different from the case of Pd/C catalyst.

Palladium-catalyzed amidocarbonylation improved by recyclable ionic liquids

Two types of ionic liquids (halide anion ionic liquids and Brensted acidic ionic liquids) were first applied to improve the palladium-catalyzed amidocarbonylation. Both the palladium catalyst and the ionic liquids could be recycled at least five times without significant loss in catalytic activity. Georg Thieme Verlag Stuttgart.

Amidoearbonylation of aldehydes utilizing cobalt oxide-supported gold nanoparticles as a heterogeneous catalyst

Cobalt oxide-supported gold-nanoparticles-catalyzed transformation of aldehydes and their equivalents to N-acyl-α-arnino acids was achieved. The desired products were obtained in moderate to excellent yields under milder reaction conditions than previous reports employing octacarbonyldicobalt as a catalyst. Copyright

METHOD OF AMIDOCARBONYLATION REACTION

A novel method of an amidocarbonylation reaction among an aldehyde compound, an amide compound, and carbon monoxide, which comprises using a palladium-supporting crosslinked-polymer composition containing palladium clusters having a major-axis length of 20 nm or shorter to conduct the amidocarbonylation reaction. Thus, an N-acyl-±-amino acid can be more efficiently and selectively synthesized in a clean reaction system. Also provided is a catalyst for use in the method.

Efficient synthesis of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation

A novel polymer incarcerated Pd catalyst (PI Pd 7c) was synthesized from amide-containing polymer 6b, and this catalyst was shown to be effective in amidocarbonylation, which is a versatile one-pot method for the preparation of N-acyl-α-amino acids. The reactions proceeded smoothly with a wide variety of substrates, and no leaching of the Pd metal to the reaction mixture was detected.

Platinum-catalyzed amidocarbonylation

The first example of platinum-catalyzed amidocarbonylation of aldehydes with amides and carbon monoxide is described. In contrast to precedent palladium catalysis, a remarkable ligand acceleration by phosphines was observed. Furthermore, an optically active N-acetyl amino acid was partially epimerized under the platinum-catalyzed conditions, while faster racemization was observed under the palladium catalysis.

A new improved palladium-catalyzed amidocarbonylation

A new and improved variant of the palladium-catalyzed amidocarbonylation to yield N-acyl-α-amino acids is described. Using Pd/C as catalyst the products were prepared in good to excellent yields (up to 98 %). Advantages of the Pd/C-catalyst with regard to former catalyst systems are demonstrated by the preparation of N-substituted non-natural amino acids which are of current interest as structural units of peptoids.

Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids

A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.