6153-17-9

Basic information

• Product Name: 3-methylidene-6-propan-2-yl-cyclohexene
• Synonyms: (R)-3-Isopropyl-6-methylene-1-cyclohexene;(R)-p-Mentha-1(7),2-diene;[R,(-)]-3-Methylene-6-(1-methylethyl)cyclohexene;beta-Phellandrene L-form
• CAS NO: 6153-17-9
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• Mol File: 6153-17-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: bp758 178-179°; bp12 53°
• Flash Point: 44°C
• Appearance: /
• Density: d1515 0.8497
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: nD20 1.4800
• CAS DataBase Reference: 3-methylidene-6-propan-2-yl-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylidene-6-propan-2-yl-cyclohexene(6153-17-9)
• EPA Substance Registry System: 3-methylidene-6-propan-2-yl-cyclohexene(6153-17-9)

Safety Data

• Hazardous Substances Data: 6153-17-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A beta-phellandrene in which the chiral centre has R configuration.

InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m1/s1

Upstream product

• 60-29-7 diethyl ether 
• 3247-45-8 1,2,3,7-tetrabromo-p-menthane 
• 7553-56-2 iodine 
• 2158-59-0 (R)-(-)-cryptone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 100190-37-2 (S)-4-iso-propyl-1-trimethylsilyloxy-1-cyclohexene 
• 5989-27-5 D-limonene 
• 763-10-0 geranyl diphosphate 

Downstream Products

• 23963-70-4 (S)-4-Isopropyl-cyclohex-1-enecarbaldehyde 
• 3247-45-8 1,2,3,7-tetrabromo-p-menthane 
• 18465-95-7 (1R)-7anti-isopropyl-5-methyl-bicyclo[2.2.2]oct-5-ene-2endo,3endo-dicarboxylic acid-anhydride 

Relevant articles and documents

Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations

The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is

TRANSFORMATIONS OF p-MENTHADIENES UNDER THE ACTION OF POTASSIUM tert-BUTANOLATE IN DIMETHYL SULFOXIDE

The products of the transformation of α- and γ-terpinenes, terpinolene, (+)-trans-isolimonene, and (+)-limonene under the action of potassium tert-butanolate in dimethyl sulfoxide contained - in addition to the α- and γ-terpinenes, isoterpinolene, p-mentha-3,8-diene and p-cymene found previously - terpinolene, α- and β-phellandrenes, p-mentha-2,4-diene (in total amount of 1-3percent), and polymers.Under these conditions, limonene is racemized.The primary products of the isomerization reaction have been identified.A supplementary scheme for the isomerization transformations of p-menthadienes is presented.