50373-53-0

Basic information

• Product Name: (S)-Lavandulol
• Synonyms: (2S)-2-Isopropenyl-5-methyl-4-hexene-1-ol;(S)-Lavandulol;[S,(+)]-5-Methyl-2-(1-methylvinyl)-4-hexen-1-ol
• CAS NO: 50373-53-0
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• Mol File: 50373-53-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Lavandulol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Lavandulol(50373-53-0)
• EPA Substance Registry System: (S)-Lavandulol(50373-53-0)

Safety Data

• Hazardous Substances Data: 50373-53-0(Hazardous Substances Data)

Upstream product

• 81757-17-7 (2S)-Benzoesaeure(2-isopropenyl-5-methyl-4-hexenyl)ester 
• 25905-14-0 lavandulyl acetate 
• 1298063-07-6 (2E,5S)-2-methyl-5-(prop-1-en-2-yl)hex-2-ene-1,6-diol 
• 1298063-18-9 (2E,5S)-2-methyl-5-(prop-1-en-2-yl)hex-2-ene-1,6-diyl diacetate 
• 1298063-83-8 (2E,5S)-1,6-bis(1-ethoxyethoxy)-2-methyl-5-(prop-1-en-2-yl)hex-2-ene 
• 1298063-90-7 (3S)-3-[(1-ethoxyethoxy)methyl]-2,6-dimethylhepta-1,5-diene 
• 869168-74-1 (6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 
• 1298063-04-3 (2E,5S)-2-methyl-5-(prop-1-en-2-yl)hex-2-enedial 
• 869162-67-4 (5S)-6-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone 
• 108-30-5 succinic acid anhydride 
• 58461-27-1 (+/-)-lavandulol 
• 1570098-81-5 (S)-4-benzyl-3-((S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enoyl)-oxazolidin-2-one 
• 7086-79-5 (3S)-4-methyl-3-(3-oxobutyl)pent-4-enal 
• 7086-79-5 (R)-4-methyl-3-(3'-oxobutyl)pent-4-enal 

Downstream Products

• 1570098-90-6 C₃₃H₄₂O₄ 

Relevant articles and documents

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.

Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone

A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.

Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol

Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.