3066-72-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 1705, 1990 DOI: 10.1016/S0040-4039(00)88859-0

InChI:InChI=1/C9H15NO/c1-2-9(11)10-8-6-4-3-5-7-8/h2,8H,1,3-7H2,(H,10,11)

Upstream product

• 61872-76-2 3-chloro-N-cyclohexylpropanamide 
• 108-91-8 cyclohexylamine 
• 79-10-7 acrylic acid 
• 814-68-6 acryloyl chloride 
• 140-88-5 ethyl acrylate 
• 74-86-2 acetylene 
• 78257-87-1 N-cyclohexyl-2-oxopropanamide 2,4,6-tri-iso-propylbenzenesulphonylhydrazone 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 33257-32-8 3-bromo-N-cyclohexylpropanamide 
• 107-13-1 acrylonitrile 
• 108-93-0 cyclohexanol 
• 110-83-8 cyclohexene 
• 15438-67-2 (3-methoxypropyl)amide 
• 2651-43-6 3-hydroxypropionamide 

Downstream Products

• 100049-79-4 3-ethylsulfanyl-propionic acid cyclohexylamide 
• 57215-71-1 2-Chloro-3-[4-(4-chloro-phenoxy)-phenyl]-N-cyclohexyl-propionamide 
• 103297-89-8 4-aza-4-cyclohexyl-2-(4-nitrophenyl)-1,6-heptadiene-3,5-dione 
• 2935-88-8 N,N'-dicyclohexyl-3,3'-disulfanediyl-bis-propionamide 
• 2935-89-9 N-cyclohexyl-3-mercaptopropionamide 
• 619-73-8 4-nitrobenzyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 1224594-09-5 N-cyclohexyl-4,4,4-trinitrobutanamide 
• 1412411-05-2 (E)-N-cyclohexyl-3-(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)acrylamide 
• 1326317-56-9 potassium N-cyclohexyl-3-(trifluoroborato)propanamide 
• 1224594-03-9 N-cyclohexyl-3-nitroisoxazole-5-carboxamide 
• 1201921-06-3 (5E)-5-benzylidene-1-cyclohexyllpyrrolidin-2-one 
• 1093682-74-6 1-benzylaziridine-2-(N-cyclohexyl)carboxamide 

Relevant academic research and scientific papers

Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions

The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.

A Potent Isoprenylcysteine Carboxylmethyltransferase (ICMT) Inhibitor Improves Survival in Ras-Driven Acute Myeloid Leukemia

Blockade of Ras activity by inhibiting its post-translational methylation catalyzed by isoprenylcysteine carboxylmethyltransferase (ICMT) has been suggested as a promising antitumor strategy. However, the paucity of inhibitors has precluded the clinical validation of this approach. In this work we report a potent ICMT inhibitor, compound 3 [UCM-1336, IC50 = 2 μM], which is selective against the other enzymes involved in the post-translational modifications of Ras. Compound 3 significantly impairs the membrane association of the four Ras isoforms, leading to a decrease of Ras activity and to inhibition of Ras downstream signaling pathways. In addition, it induces cell death in a variety of Ras-mutated tumor cell lines and increases survival in an in vivo model of acute myeloid leukemia. Because ICMT inhibition impairs the activity of the four Ras isoforms regardless of its activating mutation, compound 3 surmounts many of the common limitations of available Ras inhibitors described so far. In addition, these results validate ICMT as a valuable target for the treatment of Ras-driven tumors.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

COMPOSITONS AND METHODS FOR MODULATING UBA5

Disclosed herein, inter alia, are compositions and methods useful for inhibiting ubiquitin-like modifier activating enzyme 5.

COMPOSITIONS AND METHODS FOR INHIBITING RETICULON 4

Disclosed herein, inter alia, are compositions and methods useful for inhibiting reticulon 4(RTN4).

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Disclosed herein, inter alia, are compositions and methods useful for modulating PPP2R1 A and for the treatment of cancer.

MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity. SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH2-C(R1)H-C(=O)-OR2 (1), A-CH2-C(R1)H-C(=O)-N(R3)R4 (3), CH2=C(R1)-C(=O)-N(R3)R4 (7) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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Efficient and facile synthesis of acrylamide libraries for protein-guided tethering

A kinetic template-guided tethering (KTGT) strategy has been developed for the site-directed discovery of fragments that bind to defined protein surfaces, where acrylamide-modified fragments can be irreversibly captured in a protein-templated conjugate ad

Effective nitration of anilides and acrylamides by tert-butyl nitrite

Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.