1202-71-7

Basic information

• Product Name: 1-Azacyclododecan-2-one
• Synonyms: 1-Azacyclododecan-2-one;Undecanolactam;Azacyclododecan-2-one;Azacyclododecan-2-on
• CAS NO: 1202-71-7
• Molecular Formula: C₁₁H₂₁NO
• Molecular Weight: 183.29
• Mol File: 1202-71-7.mol

Chemical Properties

• Boiling Point: 302.517 °C at 760 mmHg
• Flash Point: 178.798 °C
• Appearance: /
• Density: 0.892 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Azacyclododecan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azacyclododecan-2-one(1202-71-7)
• EPA Substance Registry System: 1-Azacyclododecan-2-one(1202-71-7)

Safety Data

• Hazardous Substances Data: 1202-71-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Azacyclododecan-2-one is used as a building block for the synthesis of biologically active compounds, which are essential in the development of new pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a variety of complex molecules with potential therapeutic or pesticidal properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Azacyclododecan-2-one serves as a key intermediate in the production of various drugs. Its ability to form stable complexes with metal ions makes it a valuable component in the design of metal-based pharmaceuticals, which can have applications in treating a range of diseases.
Used in Agrochemical Industry:
1-Azacyclododecan-2-one is utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its role in creating stable and effective compounds contributes to the development of products that protect crops from pests and diseases, thereby ensuring food security.
Used in Polymer Production:
In the polymer industry, 1-Azacyclododecan-2-one is used in the synthesis of polymers with specific properties, such as enhanced stability, solubility, or reactivity. These polymers can be employed in various applications, including coatings, adhesives, and plastics.
Used as a Reagent in Organic Reactions:
1-Azacyclododecan-2-one acts as a reagent in a range of organic reactions, facilitating the formation of desired products with high yields and selectivity. Its versatility in participating in various reaction types, such as condensation, substitution, or rearrangement reactions, makes it a valuable tool in organic chemistry.
Used in Metal Ion Coordination Chemistry:
As a complexing agent, 1-Azacyclododecan-2-one is used in metal ion coordination chemistry to form stable complexes with metal ions. These complexes have potential applications in catalysis, sensing, and materials science, where their unique properties can be harnessed for various technological advancements.

Upstream product

• 79598-53-1 6-azidohexanoic acid 
• 112-80-1 cis-Octadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 947-04-6 2-azacyclotridecanone 
• 512-35-6 benzenesulfonic anhydride 
• 3189-61-5 cycloundecanone oxime 
• 946-89-4 cyclododecanone oxime 
• 118162-51-9 6-Azido-hexanethioic acid S-phenyl ester 
• 118162-45-1 11-azidoundecanoic acid 
• 88313-91-1 6-Amino-hexanethioic acid S-phenyl ester 
• 118162-54-2 11-Azido-undecanethioic acid S-pyridin-2-yl ester 
• 118162-53-1 11-Azido-undecanethioic acid S-phenyl ester 
• 2432-99-7 11-aminoundecanoic acid 
• 878-13-7 cycloundecanone 

Downstream Products

• 73141-78-3 1-benzylazacyclododecan-2-one 
• 1725-03-7 oxacyclododecan-2-one 
• 294-63-3 azacyclododecane 

Relevant articles and documents

A Deep Cavitand Templates Lactam Formation in Water

Cyclization reactions are common processes in organic chemistry and show familiar patterns of reaction rates vs ring size. While the details vary with the nature of bond being made and the number of unsaturated atoms, small rings typically form quickly despite angle strain, medium size rings form very slowly due to internal strains, and large rings form slowly (when they form at all) because fewer and less probable conformations bring the ends of the substrate together. High dilution is commonly used to slow the competing bi- and higher molecular processes. Here we apply cavitands to the formation of medium size lactams from ω-amino acids in aqueous (D2O) solution. The cavitands bind the amino acids in folded conformations that favor cyclization by bringing the ends closer together. Yields of a 12-membered lactam are improved 4.1-fold and 13-membered lactam 2.8-fold by the cavitand template. The results open possibilities for moving organic reactions into water even when the processes involve dehydration.

Alternative Procedures for the Macrolactamisation of ω-Azido Acids

ω-Azido acids, after activation of the carboxyl groups as mixed anhydrides, N3(CH2)nCOOCOAr (Ar = 3,5-dinitrophenyl or 2,4,6-trichlorophenyl), can be converted to macrolactams in good yields by treatment with Bu3P under high-dilution conditions; the prese

A novel synthetic route of fused tricyclic framework quinoline derivatives from readily available aliphatic amino carboxylic acid substrates

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Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions

The Br?nsted acid-catalyzed synthesis of secondary amides from ketones under mild conditions is described via transoximation and Beckmann rearrangement using O-protected oximes as more stable equivalents of explosive O-protected hydroxylamines. This methodology could be applied to highly rearrangement-selective amide synthesis from α-branched alkyl aryl ketones and performed on a 1-g scale. The presence of water is essential for this reaction, and its role was clarified by isotope-labeling experiments.

RING CLOSING METATHESIS APPROACH TO PRODUCE PRECURSORS OF NYLON 11, 12, AND 13 FROM OLEIC ACID

Provided herein is a method of producing C11, C12, and C13 nylon precursors from oleic acid or esters of oleic acid, the method involving amide formation, ring-closing metathesis, and hydrogenation. Further provided are the products of the method described. Provided herein is a method for producing a lactam, the method comprising the steps of converting oleic acid or an ester of oleic acid into an amide having a general formula of H3C-(CH2)rCH=CH-(CH2)rCONR-(CH2)n-CH=CH2, wherein n is 1, 2, or 3, and R is either hydrogen or benzyl; subjecting the amide to a ring-closing metathesis reaction to produce an intermediate having a general formula of -(CH2)rCONR-(CH2) n-CH=CH2-, wherein n is 1, 2, or 3, R is either hydrogen or benzyl, and both ends are connected to each other; and hydrogenating the intermediate to produce a saturated lactam. In certain embodiments, the saturated lactam has a formula of -NH-(CH2) 10-CO-.

Organic Compounds

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Cyanuric chloride as a mild and active Beckmann rearrangement catalyst

The first general organocatalytic Beckmann rearrangement of ketoximes into amides has been realized by the catalytic use of cyanuric chloride. Furthermore, acids such as HCl and ZnCl2 are effective as cocatalysts with cyanuric chloride. For example, azacyclotridecan-2-one, which is synthetically useful as a starting material for nylon-12, was prepared in quantitative yield by the Beckmann rearrangement of cyclododecanone oxime (100 mmol scale) catalyzed by cyanuric chloride (0.5 mol %) and ZnCl2 (1 mol %). Copyright

METHOD FOR PRODUCING REARRANGED UNSATURATED COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing a rearranged compound which can more simply and efficiently produce the rearranged compound of high utility value obtainable by the reaction such as the Beckmann rearrangement reaction and the α,β-unsaturated alcohol rearrangement reaction using a rhenium compound as a catalyst and usable in the synthesis of various compounds, and a catalyst used in this method. SOLUTION: The method for producing a rearranged compound comprises subjecting a compound having an unsaturated bond to intramolecular rearrangement or skeletal rearrangement in the presence of a rhenium compound and a boron compound. More specifically, the method produces a specific amide compound from a specific oxime compound; a specific α,β-unsaturated alcohol from a specific α,β-unsaturated alcohol; and the like.

Fast Synthesis of Amino Acid Salts and Lactams without Solvent under Microwave Irradiation

Hydroxylamine-O-sulfonic acid reacts with alicyclic ketones over SiO2 under microwave irradiation to give an amino acid salt, which cyclises in high yield to the corresponding lactam after work up in basic medium.

From Azido Acids to Macrolactams and Macrolactones

A new method is reported for the conversion of azido acids into lactams, via thioester formation and in situ azide reduction and cyclisation under high-dilution conditions; since the quantitative conversion of macrolactams to macrolactones has been shown to be feasible, this results in an indirect, alternative macrolactonisation procedure.