76155-30-1

Upstream product

• 5932-68-3 (E)-2-methoxy-4-(1-propenyl)phenol 
• 97-54-1 2-methoxy-4-propenylphenol 
• 121-33-5 vanillin 
• 97-53-0 4-allylguaiacol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 

Downstream Products

• 4483-47-0 (1S,2S,3S)-1-ethyl-5,6-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methylindane 
• 15224-73-4 (+/-)-5-acetoxy-3c-(4-acetoxy-3-methoxy-phenyl)-1r-ethyl-6-methoxy-2t-methyl-indan 
• 4483-47-0 1β-ethyl-5,6-dimethoxy-3α-(3',4'-dimethoxyphenyl)-2β-methylindane 
• 102898-11-3 (+/-)-5-ethoxy-3t-(4-ethoxy-3-methoxy-phenyl)-1r-ethyl-6-methoxy-2c-methyl-indan 
• 102898-11-3 (+/-)-5-ethoxy-3c-(4-ethoxy-3-methoxy-phenyl)-1r-ethyl-6-methoxy-2t-methyl-indan 

Relevant academic research and scientific papers

First green protocols for the large-scale preparation of γ-diisoeugenol and related dihydro(1H)indenes via formal [3+2] cycloaddition reactions

Trans-isoeugenol and related styrenes (trans-isohomogenol or O-benzylated isoeugenol), important components of the essential oil of various tropical plants, dimerize easily in the presence of catalytic amounts of BF3·OEt2 in poly(ethylene glycol) with Mn = 400 (PEG-400) or SiO2-OSO3H in MeCN via formal [3+2] cycloaddition reaction to give respective natural products (diisoeugenol and its O-substituted analog) with the 1,2-trans-2,3-trans-configuration in excellent yields. γ-Diisoeugenol scale-up preparation has also been described.

Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins

An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.

Stereocontrolled syntheses of (-)- And (+)-γ-diisoeugenol along with optically active eight stereoisomers of 7,8′-epoxy-8,7′-neolignan

It was shown that reduction of the tertiary benzylic hydroxy group of (2R,3S,4R,5S)-3,5-bis(4-benzyloxy-3-methoxyphenyl)-2,4-dimethyltetrahydro-3-furanol 17 followed by the intramolecular Friedel-Crafts reaction gave exclusively indane with (7S,7′S,8R,8′R)-2,7′-cyclo-7,8′-neolignan structure 18 along with (7S,7′R,8S,8′R)-7,8′-epoxy-8,7′-neolignan structure 19. Indane 18 was converted to (-)-γ-diisoeugenol ((-)-4). On the other hand, (2S,3R,4R,5S)-3,5-bis(4-benzyloxy-3-methoxyphenyl)-2,4-dimethyltetrahydro-3-furanol 22 did not afford indane, but the tetrahydrofuran structure with (7S,7′S,8S,8′S)-7,8′-epoxy-8,7′-neolignan structure 23 and 7′-epi-23.

A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol

A stereoselective and electrocatalytic coupling reaction of isoeugenol has been reported for the first time in a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)/boron-doped diamond (BDD) electrode system. This particular C-C bond formation and diastereoselectivi

Gold-Catalyzed Dimeric Cyclization of Isoeugenol and Related 1-Phenylpropenes in Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of 1,2,3-Trisubstituted 2,3-Dihydro-1 H -indenes

Gold-catalyzed dimerization of isoeugenol and related 1-phenylpropenes in ionic liquid enabled environmentally friendly, stereoaselective synthesis of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Dimerization of isoeugenol or isohomogenol afforded diisoeu

Anomalous behaviour of Pd(II) on phenylpropanoids

Exposure of phenylpropanoids like methyleugenol, eugenol and methylchavicol to Pd(II) chloride in acetic acid results in α,β linked unsymmetrical dimers. Dimeric coupling is characteristic of phenylpropanoids whereas cyclisation to indanes require the pre

Studies on acidic dimerization of 3,4-dioxygenated cinnamate or 1- phenylpropene to arylindane lignans

The BF3-, TsOH- or HCOOH-catalyzed dimerization of 3,4-dioxygenated cinnamate or 1-arylpropene offers a route to arylindane lignans. The structures of the products were elucidated and a mechanism is proposed for the reactions. The structures of the dimeric products assigned as aryltetralin lignans by Botta et al.