32556-70-0

Basic information

• Product Name: (R)-(+)-1-OCTYN-3-OL
• Synonyms: (R)-(+)-1-OCTYN-3-OL;(R)-1-OCTYN-3-OL;(R)-(+)-1-OCTYN-3-OL, 99% (98% EE/GLC);(R)-(+)-1-Octyn-3-ol, 98+%;(R)-1-OCTYN-3-OL, 95%, 98% EE;(R)-1-Octyn-3-ol, 98% ee;(3R)-1-Octyne-3-ol;(R)-(+)-1-Octyn-3-ol 99%
• CAS NO: 32556-70-0
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: -0
• Product Categories: Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 32556-70-0.mol
• Article Data: 41

Chemical Properties

• Melting Point: -39°C (estimate)
• Boiling Point: 100 °C20 mm Hg(lit.)
• Flash Point: 147 °F
• Appearance: clear colorless to light yellow liquid
• Density: 0.864 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.496mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• BRN: 2037704
• CAS DataBase Reference: (R)-(+)-1-OCTYN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-OCTYN-3-OL(32556-70-0)
• EPA Substance Registry System: (R)-(+)-1-OCTYN-3-OL(32556-70-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 27-36/37/39-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 32556-70-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

(R)-(+)-1-Octyn-3-ol is used as a reactant in the stereoselective preparation of cyclooxygenase metabolites of 8,9-epoxyeicosatrienoic acid.

InChI:InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h2,8-9H,3,5-7H2,1H3/t8-/m0/s1

Upstream product

• 27593-19-7 oct-1-yn-3-one 
• 818-72-4 1-Octyn-3-ol 
• 90365-18-7 N-(p-toluenesulfonyl)-L-phenylalanyl chloride 
• 54315-33-2 3-acetoxy-1-octyne 
• 53210-14-3 n-pentyl trimethylsilylethynyl ketone 
• 42541-99-1 (R)-(E)-1-Iodo-1-octene-3-ol 
• 89461-51-8 [(2S,3S)-3-pentyloxiran-2-yl]methanol 
• 128146-65-6 (R)-3-(2-Ethoxy-ethoxy)-oct-1-yne 
• 113428-14-1 (Z)-(R)-1-Bromo-oct-1-en-3-ol 
• 128241-51-0 (+)-(3R)-3-(O-tert-butyldimethylsilyl)-1-octyne 
• 131928-11-5 Propionic acid 1-ethynyl-hexyl ester 
• 85320-61-2 (R)-4-(1-Trimethylsilanylethynyl-hexyloxy)-pentan-2-one 
• 153123-10-5 (S_S,R)-(E)-2-(p-tolylsulfinyl)-1-(trimethylsilyl)-1-octen-3-ol 
• 183852-52-0 (R)-1-Triisopropylsilanyl-oct-1-yn-3-ol 

Downstream Products

• 194540-73-3 1-((R)-1-Ethynyl-hexyloxymethyl)-4-methoxy-benzene 
• 131354-45-5 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol 
• 42541-99-1 (R)-(E)-1-Iodo-1-octene-3-ol 
• 171030-11-8 15-epi-lipoxin A4 
• 131354-49-9 (R)-1-(3-acetoxy-1-octynyl)cyclohexanol 
• 164524-05-4 1-[(R)-1-((E)-2-Iodo-vinyl)-hexyloxymethyl]-4-methoxy-benzene 
• 164524-06-5 tert-Butyl-[(R)-1-((E)-2-iodo-vinyl)-hexyloxy]-diphenyl-silane 

Relevant articles and documents

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Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents

A novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents is described. The key step is the kinetic lipase-catalyzed resolution of racemic mixtures of substituted propargylic alcohols. The efficiency of this new approach was tested in the preparation of the corresponding enantiomers of 1,11-hexadecandiol derivatives ((R)-5 and (S)-5). Two strategies were tested. In the first one, the racemic intermediate 1-octyn-3-ol (1) was resolved enzymatically and then elongated with 1-bromo-9,11-dioxadodecane. Alternatively, the racemic 1 can be elongated to the corresponding racemic 17,19-dioxa-7-eicosyn-6-ol (3) first and then resolved biocatalytically. Twelve commercially available lipases were screened for the kinetic resolution of these intermediates. Among them, Candida antarctica lipase (CAL-B) and Humicola lanuginosa lipase (HLL) were the best biocatalysts for the resolution of 1 (S enantiomer 90% ee, E = 35), and 3 (R enantiomer 90% ee, E = 34), respectively.

Asymmetric Synthesis via Acetal Templates. 4. Reactions with Silylacetylenic Compounds. Formation of Chiral Propargylic Alcohols

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A Lipase Mediated Asymmetric Hydrolysis of 3-Acyloxy-1-octynes and 3-(E)-Acyloxy-1-octenes

Optical resolution of 3-propionyloxy-1-trimethylsilyl-1-octyne or 3-(E)-propionyloxy-1-octene via lipase-mediated hydrolysis gave optically pure (S)-1-trimethylsilyl-1-octyn-3-ol and (R)-(E)-1-iodo-1-octen-3-ol, respectively, in which a reversal of enantio-selectivity for hydrolysis was observed between 3-propionyloxy-1-octyn and its 1-trimethylsilylated derivative, and the effect of the acyl groups on the enantio-discrimination was also investigated.

Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions

The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses. (Figure presented.).

Asymmetric Total Syntheses of Two Possible Diastereomers of Gliomasolide e and Its Structural Elucidation

The first total syntheses of two possible diastereomers of gliomasolide E, a 14-membered macrolides isolated from the marine sponge Phakellia fusca Thiele, which was collected from the South China Sea, is reported. Highlights of the synthesis include macrolactonization through intramolecular Horner-Wadsworth-Emmons olefination, Yamaguchi-Hirao alkynylation, and base-induced elimination reactions for propargyl alcohol synthesis as the key reactions. Detailed comparison of their 1H and 13C NMR (1D and 2D NMR data) and specific rotation with those of the natural product revealed that the absolute stereochemistry of gliomasolide E should be (2E,5R,7R,9R,13R).

Coupling biocatalysis and click chemistry: One-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols

A fully convergent one-pot two-step synthesis of different chiral 1,2,3-triazole-derived diols in high yields and excellent enantio- and diastereoselectivities has been achieved under very mild conditions in aqueous medium by combining a single alcohol dehydrogenase (ADH) with a Cu-catalysed 'click' reaction. The Royal Society of Chemistry 2013.