163634-08-0

Basic information

• Product Name: Benzenepropanol,4-hydroxy-b-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-methoxy-,(bS)-
• Synonyms: Benzenepropanol,4-hydroxy-b-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-methoxy-,(E)-(+)-; (+)-Imperanene; (S)-Imperanene; Imperanene
• CAS NO: 163634-08-0
• Molecular Formula: C19H22 O5
• Molecular Weight: 330.381
• Mol File: 163634-08-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenepropanol,4-hydroxy-b-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-methoxy-,(bS)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanol,4-hydroxy-b-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-methoxy-,(bS)-(163634-08-0)
• EPA Substance Registry System: Benzenepropanol,4-hydroxy-b-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-methoxy-,(bS)-(163634-08-0)

Safety Data

• Hazardous Substances Data: 163634-08-0(Hazardous Substances Data)

Upstream product

• 370878-64-1 CHCH₂CH₂C₆H₃OCH₃OSiC₄H₉(CH₃)2CHOCHC₆H₃OCH₃OSiC₄H₉(CH₃)2Si(CH₃)3 
• 431879-30-0 (3S)-(+)-1,4-bis[4-(tert-butyldiphenylsilanyloxy)-3-methoxyphenyl]-3-(tert-butyldiphenylsilanyl-oxymethyl)but-1-ene 
• 67-56-1 methanol 
• 347359-71-1 (7RS,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 553642-31-2 2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-benzyl]-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-but-3-en-1-ol 
• 774580-84-6 C₄₀H₄₀O₁₁S₃ 
• 774580-74-4 4-(bromomethyl)-2-methoxyphenyl 4-methylbenzenesulfonate 
• 773872-07-4 4-(hydroxymethyl)-2-methoxyphenyl 4-methylbenzenesulfonate 
• 774580-83-5 3-(3-methoxy-4-(tosyloxy)phenyl)-2-((tosyloxy)methyl)propanal 
• 774580-82-4 3-(3-methoxy-4-(tosyloxy)phenyl)-2-(hydroxymethyl)-1-(tosyloxy)propane 
• 774580-81-3 3-(3-methoxy-4-(tosyloxy)phenyl)-2-((tosyloxy)methyl)propyl acetate 
• 246224-09-9 4-formyl-2-methoxyphenyl-1-(4-methylbenzenesulfonate) 
• 121-33-5 vanillin 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 

Relevant articles and documents

Synthesis of R-(-)-imperanene from the natural lignan hydroxymatairesinol

A convenient and high yielding method for the synthesis of R-(-)-imperanene, starting from the readily available natural lignan hydroxymatairesinol from Norway spruce, was developed. Hydroxymatairesinol was degraded in strongly basic aqueous conditions to

Synthesis of (S)-imperanene by using allylic substitution

(Chemical Equation Presented) Synthesis of (S)-imperanene (1) was studied by using copper-assisted allylic substitution of ArCH=CHCH(L)CH2Ar (L: leaving group) and (i-PrO)Me2SiCH2MgCl. Preliminary substitution between PhCH=CHCH(L)Me (L = AcO, PivO, MeOCO2, (2-Py)CO2) and Bu copper reagents derived from BuMgX (X = Br, Cl) and CuBr·Me2S or CuCl in 1:1-40:1 ratios suggested acetate 28 as the best substrate. To prepare 28, kinetic resolution of racemic (E)-TMSCH=CHCH(OH)CH2Ar2 (Ar2 = (p-TBSO)(m-MeO)C6H3) carried out by using the asymmetric epoxidation with (-)-DIPT afforded the corresponding epoxy alcohol and (S)-allylic alcohol. After separation by chromatography, these products were converted to (S,E)-Bu3SnCH=CHCH(OH)CH2Ar2, which upon palladium-catalyzed coupling with Ar2-I followed by acetylation gave 28 (95-98% ee). Substitution of 28 with (i-PrO)Me 2SiCH2MgCl and CuBr·Me2S in a 4:1 ratio at 0°C proceeded cleanly to produce 29 with 100% inversion in 92% yield. Finally, Tamao oxidation furnished 1.

Enantioselective synthesis of imperanene via enzymatic asymmetrization of an intermediary 1,3-diol

(Chemical Equation Presented) Using a chemoenzymatic synthetic strategy, (S)-imperanene and its (R)-enantiomer has been synthesized from vanillin in nine steps. The key step in the synthesis involves the use of Pseudomonas cepacia lipase (PS-30) to induce

Intermolecular C-H activation at benzylic positions: Synthesis of (+)-imperanene and (-)-α-conidendrin

An efficient C-H activation of primary benzylic positions by means of rhodium carbenoid induced C-H insertions is described. This key step was used in concise syntheses of (+)-imperanene and (-)-α-conidendrin.

Total synthesis of (S)-(+)-imperanene. Effective use of regio- and enantioselective intramolecular carbon-hydrogen insertion reactions catalyzed by chiral dirhodium(II) carboxamidates

The total synthesis of (S)-(+)-imperanene, a natural product found in Chinese medicine, has been completed in 12 steps from a commercially available cinnamic acid. The key step is highly enantioselective carbon-hydrogen insertion from a diazoacetate using a chiral dirhodium(II) carboxamidate catalyst. An elimination process essential to the construction has been optimized to avoid intramolecular Friedel-Crafts alkylation.

Enantioselective synthesis of imperanene, a platelet aggregation inhibitor

matrix presented Both enantiomers of imperanene, a platelet aggregation inhibitor, have been synthesized in 82-90% ee. The key step of establishing the chiral center was achieved through stereoselective alkylation with benzyl chloromethyl ether using Enders' RAMP/SAMP chiral auxiliary method. The natural product was determined to be the (S)-enantiomer through comparison of optical rotation data.