35836-72-7

Basic information

• Product Name: (1R)-(-)-NOPYL ACETATE
• Synonyms: (1R)-(-)-NOPYL ACETATE;2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl acetate(WXG00873)
• CAS NO: 35836-72-7
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.3
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 35836-72-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 253 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00751mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• CAS DataBase Reference: (1R)-(-)-NOPYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-NOPYL ACETATE(35836-72-7)
• EPA Substance Registry System: (1R)-(-)-NOPYL ACETATE(35836-72-7)

Safety Data

• WGK Germany: 3
• RTECS: RC8880000
• Hazardous Substances Data: 35836-72-7(Hazardous Substances Data)

Usage

Chemical Properties

(1R)-(-)-NOPYL ACETATE is not found in nature and has a fresh, fruity–woody odor. It is prepared by acetylation of (?)-nopol with acetic anhydride. (?)-Nopol is obtained from (?)-??-pinene and paraformaldehyde in a Prins reaction. Nopyl acetate is used in perfumes for soaps and household products.

InChI:InChI=1/C13H20O2/c1-9(14)15-7-6-10-4-5-11-8-12(10)13(11,2)3/h4,11-12H,5-8H2,1-3H3/t11-,12-/m0/s1

Upstream product

• 35836-73-8 (1R)-(-)-nopol 
• 75-36-5 acetyl chloride 
• 50-00-0 formaldehyd 
• 18172-67-3 beta-pinene 
• 75-05-8 acetonitrile 
• 81600-63-7 (1R)-nopol tosylate 
• 140632-14-0 nopylamine 
• 64-19-7 acetic acid 
• 144342-18-7 (-)-(1R)-2-(2-Iodoethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene 
• 108-24-7 acetic anhydride 

Downstream Products

• 57782-95-3 (R)-1-(2-acetoxy-ethyl)-4-isopropenyl-cyclohexene 
• 144342-07-4 (+)-(4R)-5,5-Dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-ethyl 4-toluenesulfonate 
• 14087-09-3 (1S:2S)-6.6-dimethyl-2-(2-acetoxy-ethyl)-norpinane 

Relevant articles and documents

Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: Acetylation of nopol and terpenic alcohols

The cesium salt of tungstophosphoric heteropoly acid, Cs2.5H0.5PW12O40, is an active and environmentally friendly heterogeneous catalyst for the liquid-phase acetylation of nopol and several biomass-derived terpenic alcohols (i.e., α-terpineol, nerol, geraniol, linalool, menthol, isoborneol, perillyl alcohol, carveol, isopulegol, carvacrol and nerolidol) with acetic anhydride. The resulting flavor and fragrance acetic esters, which are widely used in perfumery, household and food products, are obtained in good to excellent yields. The reactions occur at room temperature with low catalyst loadings without substantial catalyst leaching and can be performed with stoichiometric amounts of an acetylating agent in solvent free systems.

PHOSPHORUS-SUBSTITUTED QUINOXALINE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF

The disclosure relates to Phosphorus-Substituted Quinoxaline-Type Piperidine Compounds of Formula (I), and pharmaceutically acceptable derivatives thereof wherein the dashed line, A, B, Q, R1, R2, R3, R4, Y1, Z, and a are as defined herein, compositions comprising an effective amount of a Phosphorus-Substituted Quinoxaline-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Phosphorus- Substituted Quinoxaline-Type Piperidine Compound.

3α-Acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′- cyclopropane from nopylamine deamination

Deamination of nopylamine hydrochloride with sodium nitrite in acetic acid yields nopyl chloride 8, nopyl acetate 1 (R = OAc), 2-(1-acetoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene 9 and 3α-acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′-cyclopropane 12. The products are consistent with initial formation of a diazonium ion which reacts by nucleophilic attack, hydride shift or by shift of electrons of the double bond. The reaction is contrasted with the acetolysis of nopyl toluene-p-sulfonate, which yields 8,8-dimethyltricyclo[4.2.1.03,7]nonan-6-ol as the main product. The difference is suggested to result from the transition state being reached early (deamination) or late (toluene-p-sulfonate acetolysis) on the reaction coordinate.