32539-83-6

Basic information

• Product Name: 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran
• Synonyms: 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran;Nsc242988
• CAS NO: 32539-83-6
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.36634
• EINECS: 251-090-5
• Mol File: 32539-83-6.mol

Chemical Properties

• Boiling Point: 339.2 °C at 760 mmHg
• Flash Point: 155.5 °C
• Appearance: /
• Density: 0.93 g/cm³
• Vapor Pressure: 0.000184mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran(32539-83-6)
• EPA Substance Registry System: 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran(32539-83-6)

Safety Data

• Hazardous Substances Data: 32539-83-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
3,4,5,6,7,8,9,10,11,12,13,14-Dodecahydro-2H-cyclododeca[b]pyran is used as a fragrance ingredient for its pleasant, mild, sweet, and floral scent. It is incorporated into the manufacturing of perfumes and personal care products to enhance their aroma and appeal to consumers.
Used in Organic Chemistry:
Cyclododecapyran is a versatile chemical that can be used in the synthesis of other organic compounds. Its stable and non-reactive nature makes it a valuable asset in the field of organic chemistry, contributing to the development of new chemical products and processes.
Used in Industrial Applications:
Due to its stable and non-reactive nature, 3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-cyclododeca[b]pyran is considered a safe and reliable ingredient for a wide range of industrial applications. Its versatility and stability make it suitable for use in various industries, including the manufacturing of consumer goods, pharmaceuticals, and other chemical products.

InChI:InChI=1/C15H26O/c1-2-4-6-8-12-15-14(10-7-5-3-1)11-9-13-16-15/h1-13H2

Upstream product

• 38223-55-1 Pyrrolidine enamine of 2-(2-ethoxycarbonylethyl)-cyclododecanone 
• 32539-82-5 2-(3-hydroxy-prop-1-yl)-cyclododecanone 
• 40314-96-3 2-[3-(acetyloxy)propyl]cyclododecanone 
• 80007-41-6 2-(3-tert-butoxypropyl)cyclododecanone 
• 130858-87-6 3-[((E)-Cyclododec-1-enyl)oxy]-propan-1-ol 
• 830-13-7 cyclododecanone 
• 32539-89-2 (+/-)-2-allylcyclododecanone 
• 80007-43-8 2-(3-bromopropyl)cyclododecanone 
• 169138-64-1 2-(benzyloxypropyl)cyclododecanone 
• 35595-58-5 1-pyrrolidinylcyclododecene 
• 107-18-6 allyl alcohol 
• 1501-82-2 cyclododecene 
• 107-02-8 acrolein 

Downstream Products

• 106-02-5 pentadecanolide 
• 38538-07-7 12-Oximino-pentadecanolide 

Relevant articles and documents

Radical α–alkylation of ketones with unactivated alkenes under catalytic and sustainable industrial conditions

The industrially–viable aerobic α–alkylation of cyclic and acyclic ketones with allyl and alkyl alkenes in the presence of catalytic amounts of Mn2+, under homo– and heterogeneous conditions, is achieved here. The substitution of organic peroxides by Mn2+ either as a simple soluble salt or supported in zeolites, in air, generates in–situ peracid radicals and circumvents the aggressiveness of current industrial protocols, to pave the way for the design of sustainable aerobic catalytic systems. Combined reactivity and mechanistic studies show that large cyclic ketones stabilize a radical in the α–position due to a higher polarizability, steric hindrance and no proximity effects. As a proof of concept, the gram–scale synthesis of the industrial fragrance exaltolide is carried out with the Mn2+ catalysts in air, which clearly improves any other previously reported method not only in safety and environmental terms but also in number of synthetic steps and overall yield.

Method for preparing oxabicyclohexadecene

The invention discloses a method for synthesizing an important intermediate oxabicyclohexadecene of cyclopentadecanolide by a one-step method. Cyclododecene and acrolein are subjected to a cycloaddition reaction under the action of a supported metal organic catalyst to obtain an intermediate oxabicyclo hexadecene of the cyclopentadecanolide, wherein the supported metal organic catalyst is represented as Rh-X/Y, wherein X is one or more of 2 -(diphenylphosphine) methyl pyrrolidine, 2, 6-bis (diphenylphosphino) pyridine and 1-(-2-diphenylphosphine-1-naphthalene) isoquinoline, Y is a carrier andis selected from one or more of 4A molecular sieves, ordered mesoporous carbon, neutral aluminum oxide and silicon dioxide.

Method for preparing bicycle-enol ether compound

The invention relates to a method for preparing a bicycle-enol ether compound. According to the method, naphthenone and an enol ether compound are adopted as initial raw materials to prepare the bicycle-enol ether compound. The produced bicycle-enol ether compound can be applied to synthesis of musk type fragrance. The method has the advantages of being gentle in reaction condition, simple to operate, and the like.

Ring-expansion reaction of 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane catalyzed by copper ions: Use in the synthesis of 15-pentadecanolide

A catalytic procedure has been developed for the synthesis of 15-pentadecanolide (1) from readily available 1-hydroperoxy-16-oxabicyclo[10.4.0]hexadecane (2). The method is based on the reaction of hydroperoxide 2 with copper acetate (0.15-5 mol.%). Ring expansion occurred as a result of generation of tertiary bicyclohexadecyloxyl radicals 4 from hydroperoxide 2 under the action of CuI ions, β-scission of the radicals accompanied by regioselective cleavage of the bridge bond to form macrocyclic C-centered radicals 5, and their oxidation by CuII ions to (E)-11- and (E)-12-pentadecen-15-olides (6). The products obtained were converted into 15-pentadecanolide by subsequent catalytic hydrogenation over a Pd catalyst in a yield of more than 90% with respect to hydroperoxide 2.

Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds

Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo(n.4.0)alkane, 2-oxabicyclo(n.4.0)alk-1(6)-ene and 2-oxabicyclo(n.4.0)alk-1(6+n)-ene is stereoselectivity synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent and tertiary amine). These compounds lead to polyfunctionalized cyclic compounds and some natural product. We propose that this annulation reaction proceeds through a pure S(N)2-like mechanism.

Highly Regio- and Stereo-selective Annulation-Elimination Reactions of 1-Cycloalkenyl 3-Hydroxypropyl Ethers

Highly regio- and stereo-selective annulation-elimination reactions of 1-cycloalkenyl 3-hydroxypropyl ethers in the presence of triflic anhydride and tertiary amines are described; the bicyclic vinyl ethers produced are converted to 2-substituted δ-lactones, macrocyclic oxolactones and bicyclic hydroxy ethers by ozonolysis and stereoselective hydroboration.

Syntheses of 2-oxabicyclohexadec-1(6)-ene from cyclododecanone

Two methods for the synthesis of 2-oxabicyclohexadec-1(6)-ene from cyclododecanone have been suggested.The most convenient method involves the preparation of 2-(3-tert-butoxypropyl)cyclododecanone by phase-transfer catalyzed alkylation of cyclododecanobe with 1-bromo-3-tert-butoxypropane followed by removal of the protecting tert-butyl group and elimination of water. - Key words: cyclododecanone, phase-transfer catalysis, alkylation, 2-(3,3-diethoxypropyl)cyclododecanone, 2-(3,3-ethylenedioxypropyl)cyclododecanone, 12-hydroxybicyclopentadecane-15-one, 3-ethoxy-2-oxabicyclohexadec-1(16)-ene, 2-(3-chloropropen-3-yl)cyclododecanone, 2-(3-benzyloxypropyl)cyclododecanone, 2-(3-tert-butoxypropyl)cyclododecanone, 2-(3-acetoxypropyl)cyclododecanone, 2-(3-hydroxypropyl)cyclododecanone.