1020108-61-5

Basic information

• Product Name: (R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene
• Synonyms: (R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene
• CAS NO: 1020108-61-5
• Molecular Weight: 270.415
• Mol File: 1020108-61-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene(1020108-61-5)
• EPA Substance Registry System: (R,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene(1020108-61-5)

Safety Data

• Hazardous Substances Data: 1020108-61-5(Hazardous Substances Data)

Upstream product

• 1173695-83-4 C₂₂H₃₀O₂Si 
• 123-11-5 4-methoxy-benzaldehyde 
• 80-59-1 Tiglic acid 
• 1020108-59-1 (2S)-2-[(E)-2-(4-methoxyphenyl)ethenyl]-2,6-dimethylhept-5-en-1-ol 
• 1492057-09-6 C₃₄H₄₄O₂Si 
• 1492057-03-0 C₂₇H₃₈OSi 
• 1492057-02-9 (S)-((2-(2-bromoethyl)-2-methylbut-3-en-1-yl)oxy)(tert-butyl)diphenylsilane 
• 1492057-01-8 (S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylpent-4-en-1-ol 
• 1492056-99-1 (S)-tert-butyl 3-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylpent-4-enoate 
• 1492056-88-8 (S)-tert-butyl 3-(hydroxymethyl)-3-methylpent-4-enoate 
• 1020108-60-4 (2S)-2-[(E)-2-(4-methoxyphenyl)ethenyl]-2,6-dimethylhept-5-enal 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1492056-85-5 (S)-tert-butyl 3-((R)-4-isopropyl-2-oxooxazolidine-3-carbonyl)-3-methylpent-4-enoate 
• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 

Downstream Products

• 1020108-62-6 4-[(1E,3R)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol 
• 17015-60-0 bakuchiol 

Relevant articles and documents

Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

Synthesis of quaternary carbon stereogenic centers through enantioselective Cu-catalyzed allylic substitutions with vinylaluminum reagents

Catalytic enantioselective allylic substitution (EAS) reactions, which involve the use of alkyl- or aryl-substituted vinylaluminum reagents and afford 1,4-dienes containing a quaternary carbon stereogenic center at their C-3 site, are disclosed. The C-C bond-forming transformations are promoted by 0.5-2.5 mol % of sulfonate bearing chiral bidentate N-heterocyclic carbene (NHC) complexes, furnishing the desired products efficiently (66-97% yield of isolated products) and in high site (>98% SN2′)- and enantioselectivity [up to 99:1 enantiomer ratio (er)]. To the best of our knowledge, the present report puts forward the first cases of allylic substitution reactions that result in the generation of all-carbon quaternary stereogenic centers through the addition of a vinyl unit. The aryl- and vinyl-substituted vinylaluminum reagents, which cannot be prepared in high efficiency through direct reaction with diisobutylaluminum hydride, are accessed through a recently introduced Ni-catalyzed reaction of the corresponding terminal alkynes with the same inexpensive metal-hydride agent. Sequential Ni-catalyzed hydrometalations and Cu-catalyzed C-C bond-forming reactions allow for efficient and selective synthesis of a range of enantiomerically enriched EAS products, which cannot be accessed by previously disclosed strategies (due to inefficient vinylmetal synthesis or low reactivity and/or selectivity with Si-substituted derivatives). The utility of the protocols developed is demonstrated through a concise enantioselective synthesis of natural product bakuchiol.