441774-09-0

Basic information

• Product Name: 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester
• Synonyms: 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester;1,4-Piperidinedicarboxylic acid, 4-(2-propen-1-yl)-, 1-(1,1-dimethylethyl) 4-methyl ester;4-Piperidinedicarboxylic acid, 4-(2-propen-1-yl)-, 1-(1,1-dimethylethyl) 4-methyl ester;4-(2-Propen-1-yl)-1,4-piperidinedicarboxylic acid 1-tert-butyl 4-methyl ester;4-(2-Propenyl)-1,4-piperidinedicarboxylicacid-1-(1,1-dimethylethyl)4-methylester;1-tert-butyl 4-Methyl 4-allylpiperidine-1,4-dicarboxylate;N-Boc-4-(1-propylene) nipecotic acid Methyl ester;1-tert-butyl 4-Methyl 4-allylpiperidin -1,4-dicarboxylate
• CAS NO: 441774-09-0
• Molecular Formula: C₁₅H₂₅NO₄
• Molecular Weight: 283.36
• Product Categories: piperidine
• Mol File: 441774-09-0.mol

Chemical Properties

• Boiling Point: 342.4 °C at 760 mmHg
• Flash Point: 160.9 °C
• Appearance: /
• Density: 1.049
• Refractive Index: 1.474
• PKA: -2.35±0.40(Predicted)
• CAS DataBase Reference: 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester(441774-09-0)
• EPA Substance Registry System: 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester(441774-09-0)

Safety Data

• Hazardous Substances Data: 441774-09-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester is used as a key intermediate in the synthesis of peptide-based drugs and biologically active molecules for various therapeutic applications. Its role in modifying the activity and stability of these molecules contributes to the development of more effective and targeted treatments.
Used in Agrochemical Industry:
In the agrochemical sector, 1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester is utilized as a building block for the creation of novel compounds with pesticidal properties, enhancing crop protection and yield.
Used in Specialty Chemicals Industry:
1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester is employed as a crucial component in the synthesis of specialty chemicals, which find applications in various industries, including coatings, adhesives, and plastics, due to their unique properties.
Used in Biomedical Engineering:
1,4-Piperidinedicarboxylic acid, 4-(2-propenyl)-, 1-(1,1-dimethylethyl) 4-methyl ester is used in the preparation of peptide-based materials and biomaterials, which are essential in the development of advanced medical devices, drug delivery systems, and tissue engineering scaffolds, contributing to improved healthcare solutions.

InChI:InChI=1/C15H25NO4/c1-6-7-15(12(17)19-5)8-10-16(11-9-15)13(18)20-14(2,3)4/h6H,1,7-11H2,2-5H3

Upstream product

• 124443-68-1 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate 
• 106-95-6 allyl bromide 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 

Downstream Products

• 426842-70-8 4-allyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid 
• 236406-37-4 tert-butyl 4-(hydroxymethyl)-4-(prop-2-en-1-yl)piperidine-1-carboxylate 
• 693824-61-2 1-(tert-butyl) 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate 
• 1422558-61-9 C₂₁H₂₈F₃NO₂ 
• 441774-14-7 4-methoxycarbonylmethyl-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 441774-11-4 4-carboxymethyl-4-(4-hydroxy-phenylsulfanylmethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 441774-12-5 4-(4-hydroxy-phenylsulfanylmethyl)-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester 
• 203662-19-5 tert-butyl 3-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate 

Relevant articles and documents

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Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

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Facile synthesis of 4-substituted-4-aminopiperidine derivatives, the key building block of piperazine-based CCR5 antagonists

4-Substituted-4-aminopiperidine is an interesting structural motif found in a number of bioactive compounds. An efficient and convenient method for the synthesis of 4-differently substituted-4-aminopiperidine derivatives was described, employing isonipecotate as a starting material and Curtius rearrangement as a key step. The alkylation of isonipecotate could introduce various substituents at the 4-position of the piperidine ring. With this key building block, we are able to efficiently synthesize piperazino-piperidine based CCR5 antagonist in a highly convergent manner free of using toxic reagents such as diethylaluminum cyanide. The concise synthesis of a potent bioavailable CCR5 antagonist as HIV-1 entry inhibitor, Sch-350634 (1) was accomplished in excellent yield using N′-Boc-4-methyl-4-aminopiperidine 5a as a smart building block. The new methodology provides a facile and practical access to the piperazino-piperidine amide analogs as HIV-1 entry inhibitors.

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