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Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-amino-2-(2-fluorophenyl)ethanol is used as a chiral building block for the synthesis of various drugs and biologically active molecules. Its unique structure allows for the creation of novel compounds with potential therapeutic applications.
Used in Chemical Research and Development:
In the field of chemical research and development, (R)-2-amino-2-(2-fluorophenyl)ethanol is used in asymmetric synthesis and chiral catalysis. Its chiral nature makes it a valuable compound for developing new methods and techniques in these areas, potentially leading to more efficient and selective chemical reactions.

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 445-27-2 2'-Fluoroacetophenone 
• 79477-86-4 2-fluorophenylglyoxylic acid 
• 132115-73-2 methyl 2-fluoro-α-oxo-benzeneacetate 
• 394-46-7 2-fluorostyrene 
• 1312719-17-7 (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide 
• 1312718-94-7 2-(tert-butyldimethylsilyloxy)-1-(2-fluorophenyl)ethanone 
• 1072-85-1 o-fluorobromobenzene 
• 224433-98-1 [(S)-1-(2-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester 
• 224433-83-4 [(S)-1-(2-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-(4-methoxy-phenyl)-amine 
• 224433-94-7 (S)-1-(2-Fluoro-phenyl)-2-((R)-toluene-4-sulfinyl)-ethylamine 
• 224433-71-0 1-(2-Fluorophenyl)-N-(4-methoxyphenyl)methanimine 
• 224434-00-8 [(S)-1-(2-Fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid benzyl ester 

Downstream Products

• 847686-72-0 C₁₃H₁₈FNO₃ 
• 1349829-99-7 6-((2R,5R)-5-(2-fluorophenyl)-2-methylmorpholino)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one 
• 847686-72-0 C₁₃H₁₈FNO₃ 

Relevant academic research and scientific papers

Sex hormone releasing hormone receptor antagonists and uses thereof

Gonadotropin-releasing hormone receptor antagonists and uses thereofThe invention relates to the field of organic chemistry, in particular to a compound or a pharmaceutically acceptable salt thereof. Isomer, prodrug, polymorph or solvate as well as prepar

Bioproduction of Enantiopure (R)- and (S)-2-Phenylglycinols from Styrenes and Renewable Feedstocks

Enantiopure (R)- and (S)-2-phenylglycinols are important chiral building blocks for pharmaceutical manufacturing. Several chemical and enzymatic methods for their synthesis were reported, either involving multi-step synthesis or starting from a relatively complex chemical. Here, we developed one-pot simple syntheses of enantiopure (R)- and (S)-2-phenylglycinols from cheap starting materials and renewable feedstocks. Enzyme cascades consisting of epoxidation-hydrolysis-oxidation-transamination were developed to convert styrene 2 a to (R)- and (S)-2-phenylglycinol 1 a, with butanediol dehydrogenase for alcohol oxidation as well as BmTA and NfTA for (R)- and (S)-enantioselective transamination, respectively. The engineered E. coli strains expressing the cascades produced 1015 mg/L (R)-1 a in >99% ee and 315 mg/L (S)-1 a in 91% ee, respectively, from styrene 2 a. The same cascade also converted substituted styrenes 2 b–k and indene 2 l into substituted (R)-phenylglycinols 1 b–k and (1R, 2R)-1-amino-2-indanol 1 l in 95–>99% ee. To transform bio-based L-phenylalanine 6 to (R)-1 a and (S)-1 a, (R)- and (S)-enantioselective enzyme cascades for deamination-decarboxylation-epoxidation-hydrolysis-oxidation-transamination were developed. The engineered E. coli strains produced (R)-1 a and (S)-1 a in high ee at 576 mg/L and 356 mg/L, respectively, from L-phenylalanine 6, as the first synthesis of these compounds from a bio-based chemical. Finally, L-phenylalanine biosynthesis pathway was combined with (R)- or (S)-enantioselective cascade in one strain or coupled strains, to achieve the first synthesis of (R)-1 a and (S)-1 a from a renewable feedstock. The coupled strain approach enhanced the production, affording 274 and 384 mg/L (R)-1 a and 274 and 301 mg/L (S)-1 a, from glucose and glycerol, respectively. The developed methods could be potentially useful to produce these high-value chemicals from cheap starting materials and renewable feedstocks in a green and sustainable manner. (Figure presented.).

A general asymmetric synthesis of phenylglycinols

Hydride reduction and deprotection of siloxymethyl sulfinimines 2 reliably furnished chiral phenylglycinols 1 or 10 in high overall yield and enantiomeric purity.

Thiazolinone unsubstituted quinolines

Thiazolinone quinoline derivatives having no substitution on the quinoline ring active as CDK1 inhibitors which are useful as anti-proliferation agents such as for treating solid tumors.

Asymmetric synthesis of α-arylglycinols via additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines followed by 'non oxidative' Pummerer reaction

The results presented in this paper demonstrate that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) is a function of a) the reaction conditions used and b) the electronic properties of the arylidene moiety on the starting imine. High kinetically controlled (2S,R(S)) diastereoselectivity (-70 °C) was achieved for additions of imines bearing relatively electron-rich N-arylidene groups, while an electron-deficient nature of this group was found to favor the opposite stereochemical outcome. On the other hand, the reactions run under thermodynamically controlled conditions (0 °C) afforded equimolar mixtures of the diastereomeric products regardless of the pattern of substitution on the starting imines. Enantiopure α-arylglycinols were readily synthesized by 'non-oxidative' Pummerer rearrangement of diastereomerically pure β-aryl-β-N-(acyl)aminoalkyl sulfoxides, prepared from the corresponding N-PMP derivatives.