85290-51-3

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 75-52-5 nitromethane 
• 768-56-9 4-Phenylbut-1-ene 
• 51146-35-1 trimethylsilyl ester of aci-nitromethane 
• 108-30-5 succinic acid anhydride 
• 141377-53-9 1-nitro-4-phenylbutan-2-ol 
• 55628-83-6 1-(1H-imidazol-1-yl)-3-phenylpropan-1-one 
• 501-52-0 3-Phenylpropionic acid 
• 67333-73-7 1-nitro-4-phenylbutan-2-one 
• 66-99-9 β-naphthaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 108-05-4 vinyl acetate 
• 563-70-2 bromonitromethane 

Downstream Products

• 85290-51-3 (S)-1-nitro-4-phenyl-2-butanol 
• 85290-51-3 (R)-1-nitro-4-phenylbutan-2-ol 
• 80922-14-1 (E)-(4-nitrobut-3-enyl)benzene 
• 917510-17-9 triethyl(1-nitro-4-phenylbutan-2-yloxy)silane 
• 917510-18-0 tert-butyldimethyl(1-nitro-4-phenylbutan-2-yloxy)silane 
• 917510-19-1 1-nitro-4-phenylbutan-2-yl acetate 
• 67333-73-7 1-nitro-4-phenylbutan-2-one 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 5297-45-0 2-phenyl-N-tosylpropanamide 

Relevant academic research and scientific papers

Application of asymmetric Henry reaction by copper(II) complexes containing (R,R)-1,2-diaminocyclohexane with naphthyl and thiophenyl substituents

A series of Cu(II) complexes containing C1-symmetric thiophene derivatives of (1R,2R)-N1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine, namely L1, L2 and L3 were synthesized and characterized. These complexes h

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.

An efficient synthetic approach towards a single diastereomer of (2R,3R)-N 2,N 3-bis((S)-1-phenylethyl)butane-2,3-diamine via metalation and demetalation

Abstract: A facile synthetic approach has been adopted towards the synthesis of (2R,3R)-N2,N3-bis((S)-1-phenylethyl)butane-2,3-diamine via demetalation of its dichloro Zn(II) complex, which itself was separated from a mixture of dias

Synthesis and structures of copper complexes bearing unsymmetric derivatives of (R,R)-1,2-diaminocyclohexane: An efficient catalyst for asymmetric Henry reaction

A series of Cu (II) complexes bearing asymmetric derivatives of (R,R)-1,2-diaminocyclohexane were synthesised and characterised. The X-ray structures of the complexes showed distorted square planar geometry. The catalytic activities of in situ-generated c

Microwave-assisted synthesis of urea-containing zirconium metal-organic frameworks for heterogeneous catalysis of Henry reactions

Here we report the facile preparation of a urea-containing UiO-68 isoreticular zirconium metal-organic framework (MOF) with mixed dicarboxylate struts by utilizing a microwave-assisted heating method. It can work as an efficient hydrogen-bond-donating heterogeneous catalyst for Henry reactions of benzaldehydes and nitroalkanes. This mixed strut MOF exhibits improved catalytic activity compared to the pure urea-functionalized linker based analogue.

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15

The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding aldehydes with CH3NO2 catalyzed by n-C6H13NH2.

Double bond formation based on nitroaldol reaction and radical elimination: A prototype segment connection method for the total synthesis of nigricanoside A dimethyl ester

During the course of our studies toward the total synthesis of nigricanoside A dimethyl ester, a prototype method for the connection of the left- and right-half segments at the C9′–C10′ double bond was developed using a model system. The method was based

Biphenyl-Based Bis(thiourea) Organocatalyst for Asymmetric and syn -Selective Henry Reaction

A scalable, efficient and chromatography-free synthesis of a new enantiopure C 2-symmetric bis(thiourea) catalyst was accomplished from a readily available starting material. The developed strategy could be conducted on a multi-gram scale. Both the prepared enantiomers of the bis(thiourea) organocatalyst have been tested in the asymmetric Henry reaction under thoroughly optimized conditions during which an unusual solvent effect on enantioselectivity was found. The corresponding adducts were obtained in excellent yields with good to excellent enantioselectivities. The achieved high reactivity and enantioselectivity in the nitroaldol reaction of nitroalkanes with aromatic aldehydes suggests promising potential for this catalyst. Moreover, a significant syn-diastereoselectivity was observed.