2- Chloro-13*propanediol

Production of Chiral 3-Chloro-1,2-Propanediol and Glycidol by Microbial Stereoselective Degradation of Racemic 3-Chloro-1,2-Propanediol... 

Microbial Production of (/ )-3-Chloro-1,2-Propanediol from Prochiral 1,3-Dichloro-2-Propanol... 

Glycidol is rapidly hydrolysed to glyeerol (97.2%) and a-ehlorohydrin (3-chloro-1,2-propanediol, 2.8%) in 0.1 M hydroehlorie aeid, with a half-life of 10 min. At pH 7 or 8, glycidol readily reacts with glutathione to form [Pg.476]

After an oral dose of 6 mg/kg bw to rats, approximately 38% of the dose was exhaled as CO2, 50% was excreted as metabolites in the urine and 3% was present in faeces (Gingell et al., 1985). Concentrations were highest in liver, kidney and forestomach. The initial metabolic reactions are conjugation of the epoxide with glutathione, which is probably a chemical, not enzymatic, reaction, and hydration of the epoxide by epoxide hydrolase. The major metabolites in urine are jV-acetyl-5 -(3-chloro-2-hydroxypropyl)-L-cysteine (36% of the dose) and 3-chloro-1,2-propanediol (a-chlorohydrin) (4%). 

By reacting 2-aminopyridine and epichlorohydrin, Knunjanz187 obtained the hydrochloride of 3-hydroxy-3,4-dihydro-2H-pyrido[l,2-a]pyrimidine (131 R = OH). Analogous products from 4-methyl-, 5-methyl-, 5-halo- and 3,5-dibromo-substituted 2-aminopyridines have been prepared by Soviet workers.188,189 The same products arose from the reaction of 2-aminopyridines and l,3-dichloro-2-propanol.188 189 Klusis and Kuthevicius190 reacted 2-aminopyridine with 3-chloro-1,2-propanediol (127) or 2,3-... 

Figure 5.18 shows that LUMO decreases as the number of chlorines increases for alcohols. The dataset is l-chloro-2-propanol 2,2,2-trichloro-l,l-ethanediol 2,2,2-trichloroethanol 2,2-dichloroethanol 2-chloroethanol 3-chloro-1,2-propanediol 3-chloropropanol and 4-chloro-l-butanol. LUMO represents 98.51% of the variance in the linear regression equation therefore, the probability of getting a correlation of -0.9925 for a sample size of eight is less than 1%. 

The compound has only three carbons, none of which is a CH3 group. Two of the carbon signals arise from CH2 groups the other corresponds to a CH group. The only structure consistent with the observed data is that of 3-chloro-1,2-propanediol. 

Tetrahydrofuran (3.2 ml) and S-(+)-3-chloro-l,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) are mixed. The mixture of THF (3.2 ml) and S-(+)-3-chloro-1,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) is cooled to -16°C and potassium t-butoxide (3.2 ml, 1.0 M) in THF (3.2 mmol, 1.07 eq) is added at less than -10°C. The resulting slurry is stirred at -14-0°C for 1 hour. Then added to the lithium anion mixture while maintaining both mixtures at 0°C, then rinsed in with THF (2 ml). The resultant slurry is stirred at 20-23°C for 2 hour and then cooled to 6°C and a mixture of citric acid monohydrate (0.4459 g, 2.122 mmol, 0.705 eq) in water (10 ml) is added. The resultant liquid phases are separated and the lower aqueous phase is washed with ethyl acetate (12 ml). The organic layers are combined and solvent is removed under reduced pressure until a net weight of 9.73 g remains. Heptane (10 ml) and water (5 ml) are added and solvent is removed 4-nitrobenzenesulfonyl chloride y reduced pressure until a total volume of 5 ml remains. The precipitated product is collected by vacuum filtration and washed with water (7 ml). The solids are dried in a stream of nitrogen to give (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol. 

SYNS a-CHLORHYDRlN CHLORODEOXY-GLYCEROL 1-CHLORO-2.3-DIHYDROXYPROPANE 3-CHLORO-1.2-DIHYDROXYPROPANE a-CHLOROHYDRIN l-CHLOROPROPANE-2,3-DIOL I-CHLORO-23-PROPANEDIOL 3-CHLOROPROPANE-1,2-DIOL 3-CHLORO-1.2-PROPANEDIOL 3-CHLOROPROPYLENE GYLCOL Q P, 3 -DIHYDROXY-ISOPROPYL CHLORIDE 2,3-DIHYDROXYPROPYL CHLORIDE EPIBLOC GLYCERIN-a-MONOCHLOR-HYDRIN GLYCEROL CHLOROHYDRIN GLYCEROL-a-CHLOROHYDRIN GLYCEROL-a-MONOCHLOROHYDRIN (DOT) GLYCERYL-o-CHLOROHYDRIN MONOCHLORHYDRIN MONOCHLOROHYDRIN a-MONOCHLOROHYDRIN D U-5897... 

C3H4CI20 trans-1,3-dichloropropene oxide 66826-73-1 391.30 33.546 2 1675 C3H5CIN206 3-chloro-1,2-propanediol dinitrate 2612-33-1 465.65 40.594 1,2... 

C3H7CI02 3-chloro 1,2-propanediol 96-24-2 gas 3 747 1 2995 C4H603 propylene carbonate 108-32-7 in benzene 4.550 1... 

Practical applications of biocatalysis for the manufacture of chiral alcohols such as (R)-l,3-butanediol by stereospecific oxidoreduction Production of chiral C3 and C4 units via microbial resolution of 2,3-dichloro-l-propanol, 3-chloro-1,2-propanediol and related halohydrins... 

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