2511-06-0

Basic information

• Product Name: Benzene, (1-methoxyethyl)-, (S)-
• CAS NO: 2511-06-0
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• Mol File: 2511-06-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, (1-methoxyethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1-methoxyethyl)-, (S)-(2511-06-0)
• EPA Substance Registry System: Benzene, (1-methoxyethyl)-, (S)-(2511-06-0)

Safety Data

• Hazardous Substances Data: 2511-06-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1459-15-0 (R)-1-chloro-1-phenylethane 
• 108-95-2 phenol 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 438497-33-7 1-methoxy-2-{[(2R)-2-methoxy-2-phenylethyl]seleno}-3-[(1S)-1-(methylthio)ethyl]benzene 
• 207573-10-2 (1R,3S,4S)-3-((R)-2-Methoxy-2-phenyl-ethylselanyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 

Downstream Products

• 14185-42-3 (S)-methyl (1-phenylethyl)carbamate 

Relevant articles and documents

Nucleophilic substitution catalyzed by a supramolecular cavity proceeds with retention of absolute stereochemistry

While the reactive pocket of many enzymes has been shown to modify reactions of substrates by changing their chemical properties, examples of reactions whose stereochemical course is completely reversed are exceedingly rare. We report herein a class of wa

Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: Total synthesis of (+)-Sertraline

The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described (Figure presented).

Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.

Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis

The synthesis of the new chiral non-racemic sulfur-containing diselenide, di-2-methoxy-6-[(1S)-1-(methylthio)ethyl]phenyl diselenide, is described. When treated with ammonium persulfate this diselenide is transformed into the corresponding selenenyl sulfate, which acts as a strong electrophilic reagent and adds to alkenes, in the presence of methanol or water, to afford the products of selenomethoxylation or selenohydroxylation, respectively, with excellent diastereoselectivities. Starting from alkenes containing internal nucleophiles, asymmetric cyclofunctionalization reactions also resulted in good chemical yields, complete regioselectivities, and high diastereoselectivities. This sulfur-containing diselenide can also be used in catalytic amounts to promote one-pot selenenylation-deselenenylation processes, from which several types of products can be obtained in high yield and with good enantiomeric excess.

Novel polymer-bound chiral selenium electrophiles

(equation presented) Polymer-bound chiral electrophilic selenium reagents have been developed and applied to stereoselective selenenylation reactions of various alkenes. Different cleavage protocols allow further functionalization of the addition products

Efficient asymmetric selenomethoxylation and selenohydroxylation of alkenes with a new sulfur containing chiral diselenide

The synthesis of a new chiral non-racemic sulfur containing diselenide is described. The electrophilic selenium reagent, produced from this diselenide by treatment with bromine and silver triflate, has been used to effect the selenomethoxylation and the selenohydroxylation of alkenes. These addition reactions occurred with good chemical yield and with high diastereoselectivities. (C) 2000 Elsevier Science Ltd.

New nitrogen containing chiral diselenides: Synthesis and asymmetric addition reactions to olefins

A simple synthesis of two new nitrogen containing diselenides, 7 and 8, is described. These compounds were employed as starting materials to effect the asymmetric methoxyselenenylation, the hydroxyselenenylation as well as the cyclofunctionalization of ol

Asymmetric selenomethoxylation of alkenes with camphorselenenyl sulfate

By reaction with ammonium persulfate the easily available diselenide derived from (1R)-(+)-camphor was converted into the camphorselenenyl sulfate. This chiral electrophilic selenium reagent reacted at room temperature with alkenes in the presence of methanol to afford selenomethoxylated adducts in good yields and with moderate to good facial selectivity. The two diastereomeric addition products could be separated in most cases.

Asymmetric methoxyselenenylations with camphor-based selenium electrophiles

The asymmetric methoxyselenenylation of olefins was achieved with a series of camphor-based selenenyl triflates, of which the readily available 2-oxo analog 2a proved the most effective.

Asymmetric addition reactions with optimized selenium electrophiles

The synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1i, 1n, and 1v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.