122922-40-1

Basic information

• Product Name: (S)-1,2-epoxyhexane
• CAS NO: 122922-40-1
• Molecular Weight: 100.161
• Mol File: 122922-40-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-1,2-epoxyhexane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2-epoxyhexane(122922-40-1)
• EPA Substance Registry System: (S)-1,2-epoxyhexane(122922-40-1)

Safety Data

• Hazardous Substances Data: 122922-40-1(Hazardous Substances Data)

Upstream product

• 104898-02-4 (S)-2-Chloro-hexan-1-ol 
• 104898-01-3 (S)-2-bromohexanol 
• 638-29-9 n-valeryl chloride 
• 592-41-6 1-hexene 
• 1436-34-6 1,2-Epoxyhexane 
• 6920-22-5 (2S)-hexane-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 621-84-1 O-benzyl carbamate 
• 377778-35-3 (R)-(+)-4-butyl-[1,3,2]dioxathiolane 2,2-dioxide 
• 145021-05-2 (R)-t-butyl-(2-hydroxyhexyl)-sulfide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 927-77-5 n-propylmagnesium bromide 
• 2426-08-6 glycidyl n-butyl ether 
• 50-30-6 2,6-dichlorobenzoic acid 

Downstream Products

• 150890-86-1 (1R,2S)-2-Butyl-1-(4-hydroxy-phenyl)-cyclopropanecarbonitrile 
• 150890-85-0 (1R,2S)-2-Butyl-1-(4-methoxy-phenyl)-cyclopropanecarbonitrile 
• 150890-84-9 Toluene-4-sulfonic acid (R)-1-[(S)-2-cyano-2-(4-methoxy-phenyl)-ethyl]-pentyl ester 
• 134637-53-9 4-Octyloxy-benzoic acid 4-((1R,2S)-2-butyl-1-cyano-cyclopropyl)-phenyl ester 
• 1309462-99-4 C₁₅H₂₁NO₃S 
• 1309463-00-0 3-(R)-t-butyldimethylsilyloxy-1-isocyano-1-tosylheptane 
• 1309463-11-3 5-(R)-t-butyldimethylsilyloxy-7-isocyano-7-tosyldecane 
• 185760-28-5 (S)-12-(benzyloxy)-5-dodecanol 
• 4938-52-7 (S)-Hept-1-en-3-ol 
• 1423808-56-3 (4S,5S,9S)-4-(benzyloxy)-7,7-diisopropyl-1-(4-methoxyphenyl)-5,9-divinyl-2,6,8-trioxa-7-silatridecane 
• 1423808-57-4 (2S,3S)-2-(benzyloxy)-3-(((S)-hept-1-en-3-yloxy)diisopropylsilyloxy)pent-4-en-1-ol 
• 1423808-58-5 (S)-2-(benzyloxy)-2-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-dioxasilepin-4-yl)ethanol 
• 1423808-59-6 (S,Z)-methyl 4-(benzyloxy)-4-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-ioxasilepin-4-yl)but-2-enoate 
• 1422040-31-0 (5S,6S)-5-(benzyloxy)-6-((S,Z)-3-hydroxyhept-1-enyl)-5,6-dihydro-2H-pyran-2-one 

Relevant articles and documents

Design and synthesis of binuclear Co-salen catalysts for the hydrolytic kinetic resolution of epoxides

Three binuclear Co(III)-salen complexes have been synthesized based on a series of hydrophilic cyclic frameworks with different ring sizes. The catalytic performance of Co-salen complexes have further been evaluated in the hydrolytic kinetic resolution of racemic epoxides. And kinetic studies reveal that the binuclear Co-salen catalysts show a higher reactivity and better enantioselectivity in comparison to monometallic reference complex, indicating the two Co-salen units on the cyclic framework may work in a cooperative manner. Specifically, Co3, with the most flexible cyclic framework exhibits the best catalytic performance among the three catalysts, due to the efficient cooperative interactions between two cobalt centers.

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Stereospecific Epitaxial Growth of Bilayered Porous Molecular Networks

Stereocontrolled multilayer growth of supramolecular porous networks at the interface between graphite and a solution was investigated. For this study, we designed a chiral dehydrobenzo[12]annulene (DBA) building block bearing alkoxy chains substituted at the 2 position with hydroxy groups, which enable van der Waals stabilization in a layer and potential hydrogen-bonding interactions between the layers. Bias voltage-dependent scanning tunneling microscopy (STM) experiments revealed the diastereospecificity of the bilayer with respect to both the intrinsic chirality of the building blocks and the supramolecular chirality of the self-assembled networks. Top and bottom layers within the same crystalline domain were composed of the same enantiomers but displayed opposite supramolecular chiralities.

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes

New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)-propranolol and (R)-naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity. (Figure presented.).

Production Of Enantiopure alpha-Hydroxy Carboxylic Acids From Alkenes By Cascade Biocatalysis

The invention provides compositions comprising an alkene epoxidase and a selective epoxide hydrolase, such as a recombinant microorganism comprising a first heterologous nucleic acid encoding an alkene epoxidase and a second heterologous nucleic acid encoding a selective epoxide hydrolase. Exemplary alkene epoxidases include StyAB, while exemplary selective epoxide hydrolases include epoxide hydrolases from Sphingomonas, Solanum tuberosum, or Aspergillus. The invention also provides non-toxic methods of making enantiomerically pure vicinal diols or enantiomerically pure alpha-hydroxy carboxylic acids using these compositions and microorganisms.

Photocatalytic Asymmetric Epoxidation of Terminal Olefins Using Water as an Oxygen Source in the Presence of a Mononuclear Non-Heme Chiral Manganese Complex

Photocatalytic enantioselective epoxidation of terminal olefins using a mononuclear non-heme chiral manganese catalyst, [(R,R-BQCN)MnII]2+, and water as an oxygen source yields epoxides with relatively high enantioselectivities (e.g., up to 60% enantiomeric excess). A synthetic mononuclear non-heme chiral Mn(IV)-oxo complex, [(R,R-BQCN)MnIV(O)]2+, affords similar enantioselectivities in the epoxidation of terminal olefins under stoichiometric reaction conditions. Mechanistic details of each individual step of the photoinduced catalysis, including formation of the Mn(IV)-oxo intermediate, are discussed on the basis of combined results of laser flash photolysis and other spectroscopic methods.

Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography

Molecular organic cage compounds have attracted considerable attention due to their potential applications in gas storage, catalysis, chemical sensing, molecular separations, etc. In this study, a homochiral pentyl cage compound was synthesized from a condensation reaction of (S,S)-1,2-pentyl-1,2-diaminoethane and 1,3,5-triformylbenzene. The imine-linked pentyl cage diluted with a polysiloxane (OV-1701) was explored as a novel stationary phase for high-resolution gas chromatographic separation of organic compounds. Some positional isomers were baseline separated on the pentyl cage-coated capillary column. In particular, various types of enantiomers including chiral alcohols, esters, ethers and epoxides can be resolved without derivatization on the pentyl cage-coated capillary column. The reproducibility of the pentyl cage-coated capillary column for separation was investigated using nitrochlorobenzene and styrene oxide as analytes. The results indicate that the column has good stability and separation reproducibility after being repeatedly used. This work demonstrates that molecular organic cage compounds could become a novel class of chiral separation media in the near future.

The Activation of Carboxylic Acids via Self-Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation

The heterodimerizing self-assembly between a phosphoric acid catalyst and a carboxylic acid has recently been established as a new activation mode in Br?nsted acid catalysis. In this article, we present a comprehensive mechanistic investigation on this activation principle, which eventually led to its elucidation. Detailed studies are reported, including computational investigations on the supramolecular heterodimer, kinetic studies on the catalytic cycle, and a thorough analysis of transition states by DFT calculations for the rationalization of the catalyst structure-selectivity relationship. On the basis of these investigations, we developed a kinetic resolution of racemic epoxides, which proceeds with high selectivity (up to s = 93), giving the unreacted epoxides and the corresponding protected 1,2-diols in high enantiopurity. Moreover, this approach could be advanced to an unprecedented stereodivergent resolution of racemic α-chiral carboxylic acids, thus providing access to a variety of enantiopure nonsteroidal anti-inflammatory drugs and to α-amino acid derivatives.