71655-21-5

Basic information

• Product Name: (2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran
• CAS NO: 71655-21-5
• Molecular Formula: C₂₃H₄₂O₂
• Molecular Weight: 350.5784
• Mol File: 71655-21-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 444.8°C at 760 mmHg
• Flash Point: 137.3°C
• Density: 0.9g/cm³
• Vapor Pressure: 1.09E-07mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: (2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran(71655-21-5)
• EPA Substance Registry System: (2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran(71655-21-5)

Safety Data

• Hazardous Substances Data: 71655-21-5(Hazardous Substances Data)

Usage

Description

(2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran is a tetrahydropyran derivative featuring a tetrahydropyran ring fused with a long hydrocarbon chain comprising 18 carbon atoms, including two double bonds. This stereochemically-defined compound possesses a specific 2R configuration, which contributes to its unique structural and potential biological properties.

Uses

Used in Organic Synthesis:
(2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran serves as a key intermediate in organic synthesis, particularly for the development of complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2R)-2-[(3E,13E)-octadeca-3,13-dien-1-yloxy]tetrahydro-2H-pyran is utilized as a building block for the design and synthesis of novel drug candidates. Its specific stereochemistry and biological activities make it a promising candidate for the development of targeted therapeutic agents, potentially leading to new treatments for various diseases and conditions.

Upstream product

• 62592-78-3 3-(2-tetrahydropyranyloxy)propanal 
• 110-62-3 pentanal 
• 38451-25-1 C₄₆H₄₈P₂ 
• 928342-56-7 13(E)-<1-(2-tetrahydropyranyloxy)>octadecen-3-yn 
• 928342-54-5 C₁₄H₂₇I 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 629-41-4 1,8-Octanediol 
• 50816-19-8 8-bromooctanol 
• 52957-16-1 9-tetradecenyl alcohol 
• 19754-59-7 tetrahydro-2-(9-tetradecynyloxy)pyran 
• 51812-91-0 1-(2-tetrahydropyranyloxy)-9E-tetradecene 

Downstream Products

• 66410-24-0 (3Z,13Z)-3,13-octadecadienyl alcohol 

Relevant articles and documents

Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.