51479-73-3

Usage

Uses

Used in Chemical Synthesis:
O-ALLYL-2,2,2-TRICHLOROACETIMIDATE is used as a protecting group for alcohols in chemical synthesis processes. Its primary application is to protect alcohols as their allyl ethers when base-sensitive functional groups are present in the molecule. This protection is crucial to prevent unwanted side reactions and ensure the successful synthesis of the desired product.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, O-ALLYL-2,2,2-TRICHLOROACETIMIDATE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to protect alcohols as allyl ethers is particularly valuable in the development of complex molecular structures, where the protection of specific functional groups is essential for the successful synthesis of the final product.
Used in Research and Development:
O-ALLYL-2,2,2-TRICHLOROACETIMIDATE is also employed in research and development settings, where it is used to explore new chemical reactions and develop innovative synthetic methods. Its unique properties make it a valuable tool for chemists working on the design and synthesis of novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemistry.

InChI:InChI=1/C5H6Cl3NO/c1-2-3-10-4(9)5(6,7)8/h2,9H,1,3H2/b9-4-

Upstream product

• 107-18-6 allyl alcohol 
• 545-06-2 trichloroacetonitrile 

Downstream Products

• 169940-41-4 (S)-3-Allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester 
• 90711-60-7 prop-2-en-1-yl 2-iodoacetate 
• 56289-55-5 allyl cinnamate 
• 43211-62-7 allyl hexadecanoate 
• 583-04-0 vinyl benzoate 
• 203249-99-4 (R)-3-Allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol 
• 501416-10-0 (-)-(1S,3S,5S)-3-allyloxy-5-[N-(but-3-enyl)-N-(benzyloxycarbonyl)amino]cyclohept-6-enyl acetate 
• 501416-08-6 (-)-(1S,3S,5S)-3-allyloxy-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]cyclohept-6-enyl acetate 
• 501416-09-7 (-)-(1S,3S,5S)-3-allyloxy-5-[N-(but-3-enyl)-N-(2-nitrobenzenesulfonyl)amino]cyclohept-6-enyl acetate 
• 460352-60-7 (4R)-3-[(2R,3S)-3-(allyloxy)-2-methyl-5-phenylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one 
• 460352-50-5 (S)-3-((2S,3R)-3-Allyloxy-2-benzyl-pentanoyl)-4-benzyl-oxazolidin-2-one 
• 460352-61-8 (S)-3-((2S,3R)-3-Allyloxy-2-methyl-dodecanoyl)-4-benzyl-oxazolidin-2-one 
• 460352-59-4 (4R)-3-[(2S,3R)-3-(allyloxy)-2-benzyl-5-phenylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one 
• 748780-80-5 (-)-(1R,2R,3R,5R,6R)-2-azido-3-(2-propenyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl 6-ethyl ester 

Relevant academic research and scientific papers

A simple access to trichloroacetimidates

O - Trichloroacetimidates can be prepared, under mild conditions in high yield and high purity, by reacting the substrate with trichloroacetonitrile in dichloromethane and 50% aqueous potassium hydroxide mixture containing a catalytic amount of tetra-n-butylammonium hydrogen sulfate.

Stereoselective synthesis of enantiopure oxetanes, a carbohydrate mimic, an ε-lactone, and cyclitols from biocatalytically derived β-hydroxy esters as chiral precursors

Biocatalytically derived enantiopure α-substituted β-hydroxy esters serve as excellent chirons for the synthesis of a diverse set of structures such as oxetanes, a carbohydrate mimic, an ε-lactone, and carbocyclic and aromatic cyclitols. The starting materials can be easily accessed in enantiopure form from α-substituted β-keto esters by biocatalytic reduction with Klebsiella pneumoniae (NBRC 3319). Ring-closing metathesis (RCM) is one of the key transformations used to create the carbocyclic/heterocyclic frameworks reported in this article. The synthesized cyclitols were screened for their inhibitory effect on α- and β-glucosidases. Copyright

Cp?Rh(III)-Catalyzed Low Temperature C-H Allylation of N-Aryl-trichloro Acetimidamide

The readily synthesized trichloro acetimidamide was found to be an excellent directing group for the directed C-H-allylation reactions. Depending on the allylating agent used, selectively either mono- or diallylated products were readily synthesized. More

Microwave accelerated aza-claisen rearrangement

A study of microwave-induced and standard thermal Overman rearrangement of selected allylic trichloroacetimidates 1a-1f, 6-8 to the corresponding acetamides 2a-2f, 9-11 is reported. The microwave-assisted rearrangement of trifluoroacetimidate 13 is also described. Using this methodology, an efficient access to versatile allylic trihaloacetamides building synthons was established.

Synthesis, in vitro pharmacology, structure - Activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists

Novel group II metabotropic glutamate receptor (mGluR) antagonists, 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives 11 and 12, were discovered by the incorporation of a hydroxy or alkoxyl group onto the C-3 portion of selective and potent group II mGluR agonist 5, (1R,2S,5R,6R)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid. Among these compounds, (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6- fluorobicyclo-[3.1.0]hexane-2,6-dicarboxylic acid (-)-11be (MGS0039) was a highly selective and potent group II mGluR antagonist with the best pharmacokinetic profile. Compound (-)-11be exhibited high affinities for mGlu 2 (Ki = 2.38 ± 0.40 nM) and mGlu 3 (4.46 ± 0.31 nM) but low affinity for mGluR 7 (Ki = 664 ± 106 nM), and potent antagonist activities for mGlu 2 (IC50 = 20.0 ± 3.67nM) and mGluR 3 (IC50 = 24.0 ± 3.54 nM) but much less potent antagonist activities for mGlu 4 (IC50 = 1740 ± 1080 nM), mGlu 6 (IC50 = 2060 ± 1270 nM), mGlu 1 (IC50 = 93300 ± 14600 nM), and mGluR 5 (IC50 = 117000 ± 38600 nM). No significant agonist activities of (-)-11be were found for mGluRs 2, 3, 4, 6, 1, and 5 (EC50 > 100000 nM). Furthermore, (-)-11be exhibited dose-dependent oral absorption (plasma Cmax: 214 ± 56.7, 932 ± 235, and 2960 ± 1150 ng/mL for 3 mg/kg, 10 mg/kg, and 30 mg/kg, po, respectively) and acceptable blood-brain barrier penetration (brain C max: 13.2 ng/mL for 10 mg/kg, po 6 h). In this paper, we report the synthesis, in vitro pharmacological profile, and structure-activity relationships (SARs) of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid derivatives 11 and 12, and pharmacokinetic profiles of several typical compounds.

One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole

Ο-Allylations and Ο-benzylations of α-hydroxy esters (3a-3c) are performed without racemization. The reagents applied, Ο-allyl- and Ο-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.

COMPOUNDS CONTAINING A FUSED BICYCLE RING AND PROCESSES THEREFOR

Compounds of the formula STR1 wherein X is O or S--(O) t ; n is one or two; m is zero or one; Y is CH 2, O, or S--(O) t provided that Y is O or S--(O) t only when m is one; and A is STR2 are dual inhibitors of NEP and ACE. Compounds wherein A is STR3 are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.

Acid-catalysed Benzylation and Allylation by Alkyl Trichloroacetimidates

Benzyl and allyl trichloroacetimidate (1) and (2) are convenient reagents for the O-alkylation of hydroxy groups under mildly acidic conditions, wich are compatible with imide, ester, and acetal protecting groups.The base-catalyzed addition of benzyl alcohol or allyl alcohol to trichloroacetonitrile provides a simple synthesis of these imidates, but published methods for the recovery of related molecules by distillation leads to variable amounts of a rearranged product, N-alkyl trichloroacetamide.A modified procedure, suitable for the large scale synthesis of (1) and (2) without the need for a distillation step, is reported.The introduction of benzyl and allyl ethers to a variety of carbohydrate derivatives illustrates the potential of these reagents.

A New α-Amino Acid Synthesis via an Acetimidate Rearrangement

A new efficient synthesis of α-amino acids from allyl alcohol derivatives via an acetimidate rearrangement has been developed.