55695-90-4

Basic information

• Product Name: 2-(9-BROMONONYL-1-OXY)TETRAHYDROPYRAN
• Synonyms: 2-(9-BROMONONYL-1-OXY)TETRAHYDROPYRAN;2-(9-Bromononyloxy)tetrahydropyran
• CAS NO: 55695-90-4
• Molecular Formula: C₁₄H₂₇BrO₂
• Molecular Weight: 307.27
• Mol File: 55695-90-4.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 360.8°Cat760mmHg
• Flash Point: 136.4°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 2-(9-BROMONONYL-1-OXY)TETRAHYDROPYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(9-BROMONONYL-1-OXY)TETRAHYDROPYRAN(55695-90-4)
• EPA Substance Registry System: 2-(9-BROMONONYL-1-OXY)TETRAHYDROPYRAN(55695-90-4)

Safety Data

• Hazardous Substances Data: 55695-90-4(Hazardous Substances Data)

Usage

Uses

2-(9-Bromononyloxy)tetrahydropyran is a useful synthetic intermediate. It is used to prepare estradiol-adenosine hybrid compounds designed to inhibit type 1 17β-hydroxysteroid dehydrogenase. It can be also used to prepare biphenylsulfonates as S1P1 receptor antagonists.

InChI:InChI=1/C14H27BrO2/c15-11-7-4-2-1-3-5-8-12-16-14-10-6-9-13-17-14/h14H,1-13H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 55362-80-6 9-bromononan-1-ol 
• 694-54-2 tetrahydro-2H-2-pyranol 

Downstream Products

• 86252-54-2 1-(tetrahydropyran-2'-yloxy)tetradec-10-yne 
• 107495-58-9 9-<2'-(Methoxymethoxy)phenyl>-1-<(RS)-2-tetrahydropyranyloxy>nonan 
• 112999-87-8 9-<2'-(Methoxymethoxy)-3'-methylphenyl>-1-<(RS)-2-tetrahydropyranyloxy>nonan 
• 96413-04-6 11-(Tetrahydro-pyran-2-yloxy)-1-(triphenyl-λ⁵-phosphanylidene)-undecan-2-one 
• 51953-88-9 1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 55695-91-5 <9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide 
• 4549-33-1 1,9-Dibromononane 
• 187996-40-3 N-[1-Hydroxymethyl-2-oxo-11-(tetrahydro-pyran-2-yloxy)-undecyl]-benzenesulfonamide 
• 117806-56-1 2-(9-Phenyl-nonyloxy)-tetrahydro-pyran 
• 521309-77-3 (R)-(+)-1-benzyloxy-3-hydroxy-13-(tetrahydropyran-2-yloxy)tridecane 
• 64437-44-1 (E)-10-Pentadecen-1-ol 
• 86252-65-5 (2Z,13Z)-2,13-octadecadienyl acetate 
• 832726-52-0 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-[9-(tetrahydro-2H-pyran-2-yloxy)nonyloxy]but-2-ynyl]biphenyl-3-sulfonate 
• 832726-53-1 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-4-(9-hydroxynonyloxy)but-2-ynyl]biphenyl-3-sulfonate 

Relevant articles and documents

Preparation method of (E,E,Z)-10, 12, 14-hexadecatriene acetate, composition and attractant core

The invention relates to a preparation method of (E,E,Z)-10,12,14-hexadecatriene acetate, a Diaphania pyloalis attractant composition and an attractant core, and compared with the prior art, the preparation method of (E,E,Z)-10,12,14-hexadecatriene acetate has the advantages of cheap and easily available raw materials, high reaction yield, simple post-treatment, high isomerization purity of the synthesized compound, clean and environment-friendly process flow, and high activity in field. The Diaphania pyloalis attractant composition based on the (E,E,Z)-10,12,14-hexadecatriene acetate and theattractant core of the Diaphania pyloalis attractant composition have a remarkable moth-luring synergistic effect and can be stably and efficiently used for population monitoring, prevention and control of mulberry borers.

Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug-Resistant Staphylococcus aureus

In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69–77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained.

SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS

Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.