130466-96-5

Basic information

• Product Name: (R)-(+)-1,2-EPOXYNONANE, 97
• Synonyms: (R)-(+)-1,2-EPOXYNONANE, 97
• CAS NO: 130466-96-5
• Molecular Formula: C₉H₁₈O
• Molecular Weight: 142.23862
• Mol File: 130466-96-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 59 °C/6 mmHg(lit.)
• Flash Point: 45 °C
• Appearance: /
• Density: 0.837 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.146mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• CAS DataBase Reference: (R)-(+)-1,2-EPOXYNONANE, 97(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-EPOXYNONANE, 97(130466-96-5)
• EPA Substance Registry System: (R)-(+)-1,2-EPOXYNONANE, 97(130466-96-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3271 3/PG 3
• Hazardous Substances Data: 130466-96-5(Hazardous Substances Data)

Usage

General Description

(R)-(+)-1,2-Epoxynonane, 97 is a chemical compound with a high purity of 97%. It is an epoxide, which is a class of organic compounds containing a three-membered cyclic ether ring. This particular compound has a chiral center, indicated by the (R)-(+)- in its name, meaning it has a specific spatial arrangement of atoms that gives it a unique three-dimensional shape. Epoxides like (R)-(+)-1,2-Epoxynonane, 97 are useful in a variety of chemical reactions and are commonly used as intermediates in the synthesis of complex organic molecules. Due to its high purity, this compound is suitable for research and industrial applications where precise and reliable results are required.

InChI:InChI=1/C9H18O/c1-2-3-4-5-6-7-9-8-10-9/h9H,2-8H2,1H3/t9-/m1/s1

Upstream product

• 118969-84-9 (R)-Nonane-1,2-diol 
• 150620-86-3 (R)-1-O-Benzylnonane-1,2-diol 
• 111-25-1 1-bromo-hexane 
• 124-19-6 nonan-1-al 
• 152398-28-2 Chloro-acetic acid 1-tert-butylsulfanylmethyl-octyl ester 
• 152398-25-9 1-tert-Butylsulfanyl-nonan-2-ol 
• 28114-20-7 1,2-epoxynonane 
• 3761-92-0 n-hexylmagnesium bromide 
• 124-11-8 non-1-ene 
• 208589-17-7 (2R)-toluene-4-sulfonic acid 2-hydroxynonyl ester 
• 152517-49-2 (R)-1-tert-Butylsulfanyl-nonan-2-ol 

Downstream Products

• 1252660-49-3 C₃₂H₅₄O₅Si 
• 152398-49-7 (R)-6-heptyl-5,6-dihydropyran-2-one 
• 1053699-81-2 (3R,4R,5S)-4-Acetylamino-5-azido-3-((S)-1-ethyl-octyloxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 936445-88-4 2-[(7-methoxy-tetradec-4-enoyl)-methyl-amino]-propionic acid benzyl ester 

Relevant articles and documents

Synthesis and Absolute Configuration of Two Natural Phenolic Homobenzyl Esters

Two recently identified natural phenolic homobenzyl esters, isolated from Phragmipedium calurum (an orchid) and Eupatorium fortunei TURCZ (a perennial herb in the Asteraceae family), respectively, were synthesized in enantiopure forms. By comparison of the optical rotations for the synthetic and the natural samples, the absolute configurations for the natural products were reliably assigned. The synthesis also enables establishment of the absolute configuration of a closely related natural homobenzyl alcohol and provided for the first time complete physical and spectroscopic data for two other natural homobenzyl esters. Two recently isolated natural phenolic homobenzyl esters were synthesized in enantiopure forms. The absolute configurations for these natural products were thus reliably assigned. En route to the total synthesis of the first target, complete physical and spectroscopic data for two other related natural products were made available for the first time. Configuration assignment of a third natural product was also achieved.

Stereocontrol of 5,5-spiroketals in the synthesis of cephalosporolide H epimers

A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.

Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(o-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization

Lateral lithiation of (S)-4-isopropyl-2-(o-tolyl)oxazoline in diethyl ether followed by the reaction with aldehydes in the presence of TMEDA produced the addition products with stereoselectivities up to 84% de. Utilization of TMEDA as a ligand is essential for the good selectivity. Rationale for the stereoselectivity is proposed based on ab initio calculation of the lateral lithio species. The major (S,S)-products lactonized faster than the minor (S,R)-products to the corresponding 3,4-dihydroisocoumarins under acidic conditions. Thus, (3S)-3,4-dihydroisocoumarins were obtained in good optical purities up to 97% ee by sequential application of these matched stereoselective reactions.