53187-82-9

Basic information

• Product Name: (1S)-Cyclopropane-1α,2β-dimethanol
• Synonyms: (1S)-Cyclopropane-1α,2β-dimethanol;(1S,2S)-1,2-Cyclopropanedimethanol;Cyclopropane-1α,2β-dimethanol
• CAS NO: 53187-82-9
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• Mol File: 53187-82-9.mol

Chemical Properties

• Boiling Point: 236.7±8.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: (1S)-Cyclopropane-1α,2β-dimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-Cyclopropane-1α,2β-dimethanol(53187-82-9)
• EPA Substance Registry System: (1S)-Cyclopropane-1α,2β-dimethanol(53187-82-9)

Safety Data

• Hazardous Substances Data: 53187-82-9(Hazardous Substances Data)

Upstream product

• 96149-00-7 (1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 
• 889461-57-8 (+)-(S,S)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 1501-56-0 (trans)-cyclopropane-1,2-dicarbonyl dichloride 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 173239-49-1 {(1S,2S)-2-[(trityloxy)methyl]cyclopropyl}methanol 
• 821-11-4 trans-butene-1,4-diol 
• 14399-53-2 bis(iodomethyl)zinc 
• 82442-59-9 ((1S*,2S*)-cyclopropane-1,2-diyl)dimethanol 

Relevant articles and documents

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

COMPOUNDS AND THEIR METHODS OF USE

Compounds and compositions comprising compounds that inhibit glutaminase are described herein. Also described herein are methods of using the compounds that inhibit glutaminase in the treatment of cancer.

CYCLOALKANE DERIVATIVE

The present invention relates to a novel cycloalkane derivative which exhibits an excellent psychotropic action and has less side effect.

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.

Photodecarbonylation of chiral cyclobutanones

Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (-)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropaneas a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product.

Two-directional synthesis of polycyclopropanes. An approach to the quinquecyclopropane fragment of U-106305

The stereoselective preparation of three stereoisomeric tercyclopropanes and a quinquecyclopropane was investigated. Two of the tercyclopropanes were C2-symmetric and were prepared efficiently through the two-directional application of Charette's reagent-stereocontrolled cyclopropanation methodology. The nonsymmetric tercyclopropane was prepared by an iterative one-directional application of the same reagent-mediated cyclopropanation method. It was shown that the reagent-controlled transformations are far more effective for the stereoselective preparation of the tercyclopropanes than are the reactions which rely upon the influence of the substrate stereocenters. A C2-symmetric quinquecyclopropane, which possesses the repeating trans-syn stereochemistry, was prepared by iterative application of the two-directional strategy.

Iterative cyclopropanation: A concise strategy for the total synthesis of the hexacyclopropane cholesteryl ester transfer protein inhibitor U-106305

The first enantioselective total synthesis of the hexacyclopropane natural product U-106305, which is produced by Streptomyces sp. UC 11136, is described in full detail. Considerations on the biosynthesis of U-106305 and its close resemblance to the penta

Enzymes in Organic Synthesis. 24. Preparations of Enantiomerically Pure Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Monocyclic Meso Diols

Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidation of monocyclic meso diols provides a direct and convenient one-step route to a broad range of chiral γ-lactones of value as synthons in asymmetric synthesis.The general applicability of the method is demonstrated by oxidations of cis-1,2-bis(hydroxymethyl) substrates of the cyclohexyl, cyclohexenyl, cyclopentyl, cyclobutyl, cyclopropyl, and dimethylcyclopropyl series.For each diol, oxidation of the hydroxymethyl group attached to the S chiral center occurs exclusively, and the pure γ-lactone products are isolated in high (68-90percent) yields and of 100percent ee.In contrast, the enzyme does not exhibit significant enantiomeric selectivity in its catalysis of oxidations of the corresponding racemic trans diols.The stereospecificities observed, or lack thereof, are as predicted by the active-site model.