5854-52-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 1988, 1966 DOI: 10.1021/ja00961a024

Purification Methods

Crystallise it from pet ether (b 30-60o) at -20o. Also purify it as for 1-adamantyl fluoroformate below. Its IR has  max at 4.2, 5.6 and 8.4 (2380, 1786 and 1190 cm-1). [Haas et al. J Am Chem Soc 88 1988 1966, cf Moroder et al. Hoppe-Seyler’s Z Physiol Chem 357 1647 1976.]

InChI:InChI=1/C11H15ClO2/c12-10(13)14-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

Upstream product

• 75-44-5 phosgene 
• 768-95-6 1-adamanthanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 5854-61-5 N-(1-Adamantyloxycarbonyl)-L-phenylalanin 
• 5854-71-7 N^α-Adamantyloxycarbonyl-N^ε-benzyloxycarbonyl-L-lysin 
• 5854-75-1 1-adamantyl carbamate 
• 5854-72-8 1-Adamantylcarbazat 
• 935-56-8 1-chloroadamantane 
• 6221-74-5 1-methoxyadamantane 
• 6221-75-6 1-Adamantyl ethyl ether 
• 768-95-6 1-adamanthanol 
• 74975-65-8 1-adamantyl 2,2,2-trifluoroethyl ether 
• 37994-87-9 1-Adamantyl ethyl carbonate 
• 111491-78-2 Z-Arg(Adoc)2 DCHA salt 
• 86095-67-2 Z-Glu(OBu^t)-Arg(Adoc)2-OH 
• 1008530-31-1 C₂₃H₂₉NO₄ 
• 1439367-28-8 (2R,3S)-3-hydroxy-2-{[(tricyclo[3 .3.1.1 ^3’7]dec-1-yloxy)carbonyl]amino}butanoic acid 

Relevant academic research and scientific papers

Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis

An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.

Enantioselective Copper(I)/Chiral Phosphoric Acid Catalyzed Intramolecular Amination of Allylic and Benzylic C?H Bonds

Radical-involved enantioselective oxidative C?H bond functionalization by a hydrogen-atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)?H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)?H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-methoxy-NHPI (NHPI=N-hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.

Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Synthesis of 5-membered ring-type compounds as potential cholecystokinin receptor ligands

Imidazolidine-2,4-diones and 1,5-diphenyl tetrainic acid derivatives were selected in order to evaluate some 5-membered heterocyclic ring compounds as potential templates for the synthesis of CCK receptor ligands. All the compounds were evaluated in vitro towards both CCK-B and CCK-A receptors.

Rationally designed 'dipeptoid' analogues of cholecystokinin (CCK): N-terminal structure-affinity relationships of α-methyl-tryptophan derivatives

The structure-affinity relationships (SAR) between the N-terminii of a series of α-methyl-tryptophanylphenethylamide derivatives and the cholecystokinin (CCK) B receptor are discussed. A series of compounds with the general formula R-X-α-methyl-tryptophanylphenethylamide was prepared, where R is a cycloalkyl, a bicycloalkyl or a tricycloalkyl group and X is a urethane, thiourethane, amide, urea or a sulphinamide linking group. The CCK-B receptor binding affinities of these are discussed. The SAR form part of a systematic program for the rational design of 'dipeptoid' analogues of the neuropeptide CCK. Beginning with 1,1-dimethylpropyl (±)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2- [(2-phenylethyl)amino carbamate (IC50 = 4720 nM on CCK-B binding affinity) the N-terminal moiety was systematically changed for groups of varying size, shape and lipophilicity until the optimal N-terminal group was obtained and the favoured linking group chosen, resulting in the compound tricyclo[3.3.1.13,7)]dec-2-yl(R)-[(1H-indol-3-ylmethyl)-1-methyl- 2-oxo-2[(2-phenylethyl)amino]ethyl]carbamate with and IC50 = 32 nM on CCK-B receptor binding affinity.

Synthesis and application of N,N-bis-(1-adamantyloxycarbonyl) amino acids.

The preparation of novel bis-(1-adamantyloxycarbonyl) amino acid derivatives has been undertaken and their properties studied. Among them, the p-nitrophenyl esters were subsequently applied to the stepwise synthesis of Leu-enkephalin. In the last coupling step, some hydantoin formation was encountered but it could be nearly completely overcome by working with more concentrated solution. The preparation of a tyrosine derivative presented special problems owing to the existence of the phenolic group in the precursor. The relative stability of 1-adamantyloxycarbonyl as N- and O-protecting groups was also studied.