68233-94-3

Basic information

• Product Name: 7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2-ol
• Synonyms: 2-Naphthalenol, 7-methoxy-1,6-dimethyl-4-(1-methylethyl)-; 7-Methoxy-1,6-dimethyl-4-(1-methylethyl)-2-naphthalenol
• CAS NO: 68233-94-3
• Molecular Formula: C₁₆H₂₀O₂
• Molecular Weight: 244.3288
• Mol File: 68233-94-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 390.9°C at 760 mmHg
• Flash Point: 201.8°C
• Density: 1.068g/cm³
• Vapor Pressure: 1.14E-06mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: 7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2-ol(68233-94-3)
• EPA Substance Registry System: 7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2-ol(68233-94-3)

Safety Data

• Hazardous Substances Data: 68233-94-3(Hazardous Substances Data)

Upstream product

• 107203-36-1 6-methoxy-4,7-dimethyl-1,2-dihydronaphthalene 
• 107203-19-0 7-Methoxy-1.6-dimethyl-tetralon-⁽²⁾ 
• 33446-15-0 4-(4-methoxy-3-methylphenyl)butyric acid 
• 77996-11-3 4-Isopropyl-7-methoxy-1,6-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 208040-51-1 7‐methoxy‐1‐methylnaphthalen‐2‐ol 
• 1068-55-9 isopropylmagnesium chloride 
• 208040-69-1 7‐methoxy‐1,6‐dimethyl‐1‐((trimethylsilyl)oxy)naphthalen‐2(1H)‐one 
• 5060-82-2 7-methoxy-2-naphthol 
• 208040-56-6 1‐hydroxy‐7‐methoxy‐1,6‐dimethylnaphthalen‐2(1H)‐one 
• 2954-68-9 4-(4-methoxy-3-methylphenyl)-4-oxo-butyric acid ethyl ester 
• 80736-45-4 1,2,3,4-Tetrahydro-4-isopropyl-7-methoxy-6-methyl-1-naphthalenone 
• 70143-26-9 1,2,3,4-tetrahydro-1,2-dihydroxy-4-isopropyl-7-methoxy-1,6-dimethylnaphthalene 
• 70143-25-8 7-Methoxy-α-calacorene 
• 70143-24-7 4-(4-methoxy-3-methylphenyl)-5-methylhexanoic acid 

Downstream Products

• 56051-00-4 1-hydroxy-4-isopropyl-7-methoxy-1,6-dimethylnaphthalen-2(1H)-one 
• 77401-25-3 2,7-dihydroxycadalene 
• 56362-72-2 Lacinilene C 7-methyl ether 
• 102517-55-5 (S)-(-)-lacinilene C methyl ether 

Relevant articles and documents

Oxazoline-mediated synthesis of the Gossypium sesquiterpene lacinilene C-7 methyl ether and a structurally related HIV-1 reverse transcriptase inhibitor

An efficient synthesis of the phytoalexin, lacinilene C-7 methyl ether, via its probable biosynthetic precursor, 2-hydroxy-7-methoxycadalene is described. A related synthesis of a HIV-1 reverse-transcriptase inhibitor is briefly discussed.

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: Synthesis of lacinilene derivatives

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N′-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95:5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.

Gossypium Cadinanes and Their Analogues: Synthesis of Lacinilene C, 2,7-Dihydroxycadalene, and Their Methyl Ethers

The total synthesis of lacinilene C methyl ether has been accomplished in ten steps with an overall, optimal yield of 38percent by starting with o-methylanisole.Formation of the key α-aryl-α-ketol functionality, which is particularly sensitive to oxidation, was accomplished by stepwise oxidation reactions based on the use of N-methylmorpholine N-oxide/osmium tetraoxide acting on alkene and trimethylsilyl enol ether functionality.Other oxidations could be accomplished by using dichlorodicyanobenzoquinone to generate unsaturation adjacent to the α-ketol group or to form substituted naphtalenes.These reactions permitted adjustment of the oxidation level and oxygenation pattern of the key intermediate, 7-methoxy-α-calacorene (3,4-dihydro-4-isopropyl-7-methoxy-1,6-dimethylnaphthalene), to accomplish the synthesis of 2-hydroxy-7-methoxycadalene, 2,7-dihydroxycadalene, 7-methoxycadalene, and 7-hydroxycadalene, in addition to lacinilene C and its methyl ether.