89015-46-3

Basic information

• Product Name: Benzene, 4-(1,5-dimethyl-4-hexenyl)-2-methoxy-1-methyl-
• CAS NO: 89015-46-3
• Molecular Formula: C16H24O
• Molecular Weight: 232.366
• Mol File: 89015-46-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzene, 4-(1,5-dimethyl-4-hexenyl)-2-methoxy-1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 4-(1,5-dimethyl-4-hexenyl)-2-methoxy-1-methyl-(89015-46-3)
• EPA Substance Registry System: Benzene, 4-(1,5-dimethyl-4-hexenyl)-2-methoxy-1-methyl-(89015-46-3)

Safety Data

• Hazardous Substances Data: 89015-46-3(Hazardous Substances Data)

Upstream product

• 88947-99-3 2-Hydroxy-2-methyl-6-(3-methoxy-4-methylphenyl)-heptane 
• 179754-27-9 Toluene-4-sulfonic acid 2-(3-methoxy-4-methyl-phenyl)-6-methyl-hept-5-enyl ester 
• 3556-81-8 1-(3-methoxy-4-methylphenyl)ethan-1-one 
• 130921-08-3 Methyl 4-(3-Methoxy-4-methylphenyl)pentanoate 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 917757-15-4 (3-methoxy-4-methylphenyl)boronic acid 
• 1311301-46-8 C₁₃H₁₈N₂O₄S 
• 167960-11-4 3-bromo-4-methylstyrene 
• 104-87-0 4-methyl-benzaldehyde 
• 36276-24-1 3-bromo-4-methyl-benzaldehyde 
• 107-31-3 Methyl formate 
• 124-41-4 sodium methylate 
• 113706-59-5 2-(3-methoxy-4-methylphenyl)-6-methylhept-5-en-2-ol 
• 116778-46-2 Ethyl 5-(3-methoxy-4-methylphenyl)hexanoate 

Downstream Products

• 59684-62-7 Xanthorrhizol 
• 113706-54-0 13-hydroxyxanthorrhizol 

Relevant articles and documents

Total Synthesis and Antibiotic Properties of Amino-Functionalized Aromatic Terpenoids Related to Erogorgiaene and the Pseudopterosins

Following a concept recently introduced by Hergenrother,[6] the present study addresses the question of whether certain antimicrobially active aromatic (marine) natural products can be converted into more potent broad-spectrum antibiotics by introducing an aminoalkyl side chain. To this end, phenolic mono- and sesquiterpenoids (incl. carvacrol, xanthorrhizol, and 7-hydroxycalamene) as well as the diterpenes 7-hydroxyerogorgiaene and 9-deoxypseudopterosin A were converted into amino-functionalized analogs that display either an amino-methyl or a 2-amino-ethoxy substituent in place of (or next to) the OH group. This was achieved either by Pd-catalyzed nitromethylation/reduction of the aryltriflates, by O-alkylation of the phenols with bromoacetonitrile and subsequent reduction, or by ortho-hydroxymethylation/amination. During the study, an efficient enantioselective total synthesis of 7-hydroxyerogorgiaene (8 steps, 29 % overall yield) and 9-deoxypseudopterosin A (9 steps, 30 % overall yield) was elaborated using an asymmetric cobalt-catalyzed hydrovinylation (91 % ee) of 3-methoxy-4-methyl-styrene as the chirogenic step. Other important C?C bond forming steps include a Pd-catalyzed Suzuki cross-coupling and diastereoselective Lewis acid-mediated cyclization reactions. A total of 16 amino derivatives of natural products were prepared and subsequently tested for their antibacterial properties. Some of the diterpene-derived amines showed high efficacy, not only against Gram-positive (S. aureus SG511, S. aureus HG003, B. subtilis 168; MIC=0.5 to 2 μg/ml), but also against Gram-negative bacterial strains (E. coli K12; E. coli I-11276b; MIC=8 to 32 μg/ml). This clearly supported the underlying working hypothesis.

A short synthesis of bisabolane sesquiterpenes

A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials.

A formal total synthesis of xanthorrhizol based on nucleophilic opening of vinyloxirane by arylcopper reagent

A formal total synthesis of xanthorrhizol was achieved in short step sequence involving the nucleophilic opening of methyl 4,5-epoxy-(2E)-pentenoate (1) by arylcopper reagent.