4727-18-8

Basic information

• Product Name: Cyclopentadecanone, 2-hydroxy
• Synonyms: Cyclopentadecanone, 2-hydroxy;2-Hydroxy-1-cyclopentadecanone;2-Hydroxycyclopentadecane-1-one;2-Hydroxycyclopentadecanone;Exaltoin
• CAS NO: 4727-18-8
• Molecular Formula: C₁₅H₂₈O₂
• Molecular Weight: 240.38
• Mol File: 4727-18-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 57-58 °C
• Boiling Point: 381.3°C at 760 mmHg
• Flash Point: 162.8°C
• Appearance: /
• Density: 0.926g/cm³
• Vapor Pressure: 2.22E-07mmHg at 25°C
• Refractive Index: 1.458
• PKA: 13.42±0.20(Predicted)
• CAS DataBase Reference: Cyclopentadecanone, 2-hydroxy(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentadecanone, 2-hydroxy(4727-18-8)
• EPA Substance Registry System: Cyclopentadecanone, 2-hydroxy(4727-18-8)

Safety Data

• Hazardous Substances Data: 4727-18-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 47, p. 3266, 1969 DOI: 10.1139/v69-540

InChI:InChI=1/C15H28O2/c16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15(14)17/h14,16H,1-13H2

Upstream product

• 1119-79-5 pentadecanedioic acid diethyl ester 
• 36575-82-3 dimethyl pentadecanedioate 
• 112-86-7 cis-13-docosenoic acid 
• 616-01-3 13,14-dihydroxy-behenic acid 
• 1119-77-3 ethyl 13-oxotridecanoate 
• 502-72-7 cyclopentadecanone 
• 104281-50-7 1-trimethylsiloxycyclopentadecene 
• 68377-38-8 ethylene pentadecanedioate 
• 420813-63-4 butylene pentadecanedioate 
• 1593-55-1 azelaic acid monoethyl ester 
• 14113-01-0 Ethyl hydrogen suberate 
• 23427-69-2 cyclopentadecane-1,2-dione 
• 13756-61-1 13,14-Dihydroxy-behensaeure-ethylester 
• 1190-57-4 Diethyl-3-hydroxypentadecane-dioat 

Downstream Products

• 502-72-7 cyclopentadecanone 
• 1119-79-5 pentadecanedioic acid diethyl ester 
• 98348-19-7 2-Acetoxy-cyclopentadecanon-⁽¹⁾ 
• 544445-81-0 2-mesyloxycyclopentadecanone 
• 60447-89-4 2-bromocyclopentadecan-1-one 
• 56345-01-8 (2E)-cyclopentadec-2-en-1-one 
• 32247-08-8 cyclopentadec-2-en-1-one 
• 17344-52-4 Cyclopentadecandiol-(1,2) 
• 23427-69-2 cyclopentadecane-1,2-dione 
• 4727-17-7 cyclopentadecanol 
• 295-48-7 cyclopentadecane 
• 1460-18-0 pentadecanedioic acid 

Relevant articles and documents

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Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism

A catalytic pinacol-type reductive rearrangement reaction of internal 1,2-diols is reported herein. Several scaffolds not usually amenable to pinacol-type reactions, such as aliphatic secondary–secondary diols, undergo the transformation well without the need for prefunctionalization. The reaction uses a simple boron catalyst and two silanes and proceeds through a concerted, stereoinvertive mechanism that enables the preparation of highly enantiomerically enriched products. Computational studies have been used to rationalize the preference for migration over direct deoxygenation.

A practical synthesis of (E)-2-cyclopentadecen-1-one: an important precursor of macrocyclic muscone

A practical synthesis of (E)-2-cyclopentadecen-1-one (E)-2 which is an important precursor of macrocyclic muscone (1) was investigated. Olefination of 2-mesyloxycyclopentadecanone (7c) with strong acid such as sulfuric acid or trifluoromethanesulfonic acid afforded the desired (E)-2 in high yield with extremely high stereoselectivity, which was treated with methylmagnesium cuprate to furnish the dl-muscone in good yield.