73494-49-2

Basic information

• Product Name: (R)-alpha-methylbenzenebutanol
• Synonyms: (R)-alpha-methylbenzenebutanol;(R)-α-Methylbenzene-1-butanol;(R)-5-phenylpentan-2-ol
• CAS NO: 73494-49-2
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24414
• EINECS: 277-482-6
• Mol File: 73494-49-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-alpha-methylbenzenebutanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-alpha-methylbenzenebutanol(73494-49-2)
• EPA Substance Registry System: (R)-alpha-methylbenzenebutanol(73494-49-2)

Safety Data

• Hazardous Substances Data: 73494-49-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-alpha-Methylbenzenebutanol is used as a key intermediate in the synthesis of pharmaceuticals for its unique chemical structure and stereochemistry, contributing to the development of new drugs with specific therapeutic properties.
Used in Fragrance Industry:
(R)-alpha-Methylbenzenebutanol is used as a fragrance ingredient in the cosmetics and personal care products industry due to its slight floral aroma, enhancing the sensory experience of these products.
Used in Asymmetric Synthesis:
(R)-alpha-Methylbenzenebutanol is used as a chiral auxiliary in asymmetric synthesis reactions, which are crucial for producing enantiomerically pure compounds that can have different biological activities and are often required in the pharmaceutical industry.
Used in Consumer Products:
(R)-alpha-Methylbenzenebutanol is used in various consumer products as it is considered a low-toxicity compound and is generally safe for use, ensuring the safety and quality of the final products.

Upstream product

• 108-05-4 vinyl acetate 
• 2344-71-0 5-phenylpentan-2-ol 
• 1075-74-7 5-phenylpent-1-ene 
• 538-68-1 pentylbenzene 
• 2235-83-8 5-phenyl-2-pentanone 
• 14371-10-9 (E)-3-phenylpropenal 
• 67470-74-0 (2S,3R,E)-5-phenylpent-4-ene-2,3-diol 
• 87118-98-7 4S-Benzyloxy-1-phenyl-1-pentanone 
• 611-71-2 MANDELIC ACID 
• 927385-39-5 (S)-5-phenylpent-4-yn-2-ol 
• 536-74-3 phenylacetylene 
• 66820-55-1 (E)-5-phenylpent-4-ene-2,3-diol 
• 2344-70-9 1-phenyl-3-butanol 
• 87068-86-8 C₁₉H₂₀O₄ 

Downstream Products

• 158514-61-5 (S)-4-bromo-2-(5-phenyl-2-pentoxy)anisole 
• 158514-62-6 (R)-4-bromo-2-(5-phenyl-2-pentoxy)anisole 
• 158514-50-2 (S)-(-)-4-[4-methoxy-3-(5-phenylpent-2-yloxy)phenyl]benzoic acid 
• 158514-49-9 (R)-(+)-4-[4-methoxy-3-(5-phenylpent-2-yloxy)phenyl]benzoic acid 
• 63790-07-8 1-methyl-4-phenylbutyl methanesulphonate 
• 1429391-71-8 1-(4-chloropentyl)benzene 
• 1429484-72-9 (S)-5-hydroxy-2-methyl-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinolin-4(1H)-one 
• 1429484-73-0 (2S)-1-formyl-5-hydroxy-2-methyl-4-oxo-3-(3-oxobutyl)-7-[(R)-5-phenyl-2-pentyloxy]-2,3-dihydroquinoline 
• 78513-72-1 (6S,6aR)-5,6,6a,7-tetrahydro-1-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline-9(8H)-one 
• 1429484-74-1 (6S,6aR,10aR)-5,6,6a,7,10,10a-hexahydro-1-acetoxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline-9(8H)-one 
• 77209-75-7 (6S,6aR,9R,10aR)-5,6,6a,7,8,9,10,10a-octahydro-1-acetoxy-9-hydroxy-6-methyl-3-[(R)-5-phenyl-2-pentyloxy]benzo[c]quinoline hydrochloride 

Relevant articles and documents

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A series of vinylogous amphetamine analogs was synthesized and examined for their activity at biogenic amine transporters and serotonin-2 receptor (5-HT2) subtypes. (1S,3E)-1-Methyl-4-phenyl-but-3-enylamine (S-6) is a potent dual dopamine/serotonin (DA/5-HT) releaser with no activity at 5-HT2 receptors. This unique profile of actions suggests that analog S-6 is a viable lead compound for identifying new structural classes of DA/5-HT releasers with therapeutic benefit and reduced abuse liability.

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Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through Cu-Catalyzed additions of alkylboronates to aldehydes

The first catalytic enantio- and diastereoselective synthesis of 1,2-hydroxyboronates is reported. Reactions are promoted by a readily available chiral monodentate phosphoramidite-copper complex in the presence of an alkyl 1,1-diboron reagent. Products contain two contiguous stereogenic centers and are obtained in up to 91% yield, >98:2 d.r., and 98:2 e.r. The reaction is tolerant of aryl and vinyl aldehydes, and the 1,2-hydroxyboronate products can be transformed into versatile derivatives. Mechanistic experiments indicate control of absolute stereochemistry of the α-boryl component.

Levonantradol: Asymmetric synthesis and structural analysis

The first asymmetric synthesis of a synthetic cannabinoid levonantradol was accomplished, and the 3-D solution structure of its core architecture was confirmed by NMR and computational methods. The Royal Society of Chemistry 2013.

Copper(I)-catalyzed boryl substitution of unactivated alkyl halides

Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.

Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups

P-Chiral diphosphine ligands, (S,S)-1,2-bis(tert-butylmethylphosphino)ethane [(S,S)-t-Bu-BisP*], (R,R)-bis(tert-butylmethylphosphino)methane [(R,R)-t-Bu-MiniPHOS], and (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline [(R,R)-QuinoxP*], were applied to the rhodium-catalyzed enantioselective hydrosilylation of simple ketones. The corresponding secondary alcohols were obtained in high yields with good to excellent enantiomeric excesses of up to 99%.

A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions

A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.

Asymmetric hydrosilylation of ketones using trans-chelating chiral peralkylbisphosphine ligands bearing primary alkyl substituents on phosphorus atoms

Asymmetric hydrosilylation of simple ketones with diphenylsilane proceeded at -40 °C in the presence of a rhodium complex (0.001 - 0.01 molar amount) coordinated with a trans-chelating chiral bisphosphine ligand bearing linear alkyl substituents on the phosphorus atoms, (R,R)-(S,S)-Et-, Pr-, or BuTRAP, giving the corresponding optically active (S)- secondary alcohols with up to 97% ee. The asymmetric hydrosilylation using TRAP ligands with bulkier P-substituents resulted in much lower enantioselectivities. The EtTRAP-rhodium catalyst was also effective for asymmetric hydrosilylation of keto esters with a coordination site for a rhodium atom (up to 98% ee). Optically active symmetrical diols were obtained with up to 99% ee from the corresponding diketones via the asymmetric reduction using 2.5 molar amounts of diphenylsilane.

Biocatalytic Asymmetric Hydroxylation of Hydrocarbons with the Topsoil-Microorganism Bacillus megaterium

A Bacillus megaterium strain was isolated from topsoil by a selective screening procedure with allylbenzene as a xenobiotic substrate. This strain performed the hydroxylation chemoselectively (no arene oxidation and overoxidized products) and enantioselectively (up to 99% ee) in the benzylic and nonbenzylic positions of a variety of unfunctionalized arylalkanes. Salycilate and phenobarbital, which are potent inducers of cytochrome P-450 activity, changed the regioselectivity of the microbial CH insertion, without an effect on the enantioselectivity. The biotransformation conditions were optimized in regard to product yield and enantioselectivity by variation of the oxygen-gas supply and the time of the substrate addition. The different product distributions (α- versus β-hydroxylated product) that are obtained on induction of cytochrome P-450 enzyme activity demonstrate the involvement of two or more hydroxylating enzymes with distinct regioselectivities in this biotransformation. An oxygen-rebound mechanism is assumed for the cytochrome P-450-type monooxygenase activity, in which steric interactions between the substrate and the enzyme determine the preferred face of the hydroxy-group transfer to the radical intermediate.

Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium-MOP

Asymmetric hydrosilylation of simple terminal alkenes (RCH=CH2) with trichlorosilane at 40 deg C in the presence of 1*10-3 or 1*10-4 molar amounts of palladium catalyst prepared in situ from 3-C3H5)>2 and (S)-2-diphenylphosphino-2'-methoxy-1,1'-binaphthyl ((S)-MeO-MOP) proceeded with unusual regioselectivity and with high enantioselectivity to give high yields of 2-(trichlorosilyl)alkanes together with a minor amount of 1-(trichlorosilyl)alkanes.Optically active alcohols, RCH(OH)CH3, were obtained by oxidation of the carbon-silicon bond.Regioselectivities for forming 2-silylalkanes over 1-silylalkanes and enantiomeric purities of alcohols are as follows: R=n-C4H9: 89/11, 94percent ee (R).R=n-C6H13: 93/7, 95percent ee (R).R=n-C10H21: 94/6, 95percentee (R).R=PhCH2CH2: 81/19, 97percentee (S).R=PhCH2CH2CH2: 80/20, 92percent ee (R).R=cyclo-C6H11: 66/34, 96percent ee (R).A similar hydrosilylation of 1-alkenes, 4-pentenyl benzoate and 1,5-heptadiene gave corresponding 2-alkanols of 90percent ee and 87percent ee, respectively, the ester carbonyl and the internal double bond remaining intact.