3164-73-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Nitromethylcyclohexanol is used as an intermediate in the synthesis of pharmaceuticals for its versatile building block properties, enabling the creation of various organic compounds.
Used in Agrochemical Industry:
1-Nitromethylcyclohexanol is used as an intermediate in the production of insecticides and fungicides, as well as other agricultural chemicals, due to its ability to be a building block for various organic compounds.

InChI:InChI=1/C7H13NO3/c9-7(6-8(10)11)4-2-1-3-5-7/h9H,1-6H2

Upstream product

• 75-52-5 nitromethane 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 108-94-1 cyclohexanone 
• 110-89-4 piperidine 
• 110-83-8 cyclohexene 
• 563-70-2 bromonitromethane 
• 109-89-7 diethylamine 

Downstream Products

• 229486-45-7 1,1-bis(nitromethyl)cyclohexane 
• 4000-72-0 1-aminomethylcyclohexanol 
• 5330-61-0 1-nitromethyl-cyclohexene 
• 335458-24-7 1-benzylthio-1-nitromethylcyclohexane 
• 27861-39-8 (nitromethylene)cyclohexane 
• 58107-53-2 N-{(1-hydroxycyclohexyl)methyl}-4-methylbenzenesulfonamide 
• 1430853-08-9 C₁₆H₂₀ClNO₄ 
• 1430853-20-5 (4S,5R)-4-phenyl-5-nitro-1-oxaspiro[5.5]undecan-2-one 
• 1430853-07-8 C₁₆H₂₁NO₄ 
• 1430853-28-3 (4S,5R)-4-(4-methoxyphenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 
• 1430853-27-2 (4S,5R)-4-(4-methylphenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 
• 1430853-26-1 (4S,5R)-4-(4-nitrophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 
• 1430853-23-8 (4S,5R)-4-(4-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 
• 1430853-22-7 (4S,5R)-4-(3-chlorophenyl)-5-nitro-1-oxaspiro[5.5]undecan-2-one 

Relevant academic research and scientific papers

Ketones as electrophile in nitroaldol reaction: Synthesis of β,β-disubstituted-1,3-dinitroalkanes and allylic nitro compounds

β,β-Disubstituted-1,3-dinitro compounds were obtained exclusively with an overall yield of 83% through a domino nitroaldol/elimination/1,4-addition process, when excess nitromethane was added to cyclohexanone or butanone using DBU (1,8-diazabicyclo[5.4.0]

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

Method for taking DAST reagent as removing reagent to synthetize conjugated nitroolefin substituted series derivative

The invention discloses a preparation method of taking a DAST reagent as a removing reagent to synthesize a conjugated nitroolefin substituted series derivative. The preparation method comprises the following steps that a carbonyl compound (compound II) i

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid

DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.

Henry reaction catalyzed by recyclable [C4dabco]OH ionic liquid

DABCO-based ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been used as an efficient catalyst for Henry reaction of various carbonyl compounds with nitroalkanes affording very high yields within a short duration. This method is very simple, clean and avoids hazardous organic solvents. The catalyst can be easily recovered and recycled several times.

RECYCLABLE CHIRAL CATALYST FOR ASYMMETRIC NITROALDOL REACTION AND PROCESS FOR THE PREPARATION THEREOF

The present invention relates to preparation of highly efficient chiral recyclable homogeneous catalysts generated in situ by the reaction of chiral oligomeric [H4] ligands and a metal salt taken in 1:1 molar ratio for asymmetric nitroaldol reaction, wherein nitroaldol reactions of various aldehydes such as aromatic, aliphatic α,β-unsaturated aldehydes, alicyclic aldehydes and nitroalkenes were carried out to produce optically active β-nitroalcohols in high yield and with moderate to excellent enantioselectivity (ee up to >95%) in presence of a base and an optically active chiral recyclable homogeneous catalyst represented by the following formula (I).

Asymmetric organocatalytic Michael-hemiacetalization reaction: Access to chiral spiro cis-δ-lactones by in situ oxidation of spiro δ-lactols

Asymmetric tandem Michael-hemiacetalization reaction between 1-nitromethylcycloalkanol and α,β-unsaturated aldehydes was investigated, which provided an efficient and facile synthesis for spiro cis-δ-lactones by in situ oxidation of spiro δ-lactols in goo

Recyclable Cu(II)-macrocyclic salen complexes catalyzed nitroaldol reaction of aldehydes: A practical strategy in the preparation of (R)-phenylephrine

Chiral macrocyclic salen ligands 1′-3′ derived from 1R,2R-(-)-1,2-diaminocyclohexane, 1R,2R-(+)-1,2-diphenyl-1,2-diaminoethane and (R)-(+)-1,1′-binaphthyl-2,2′-diamine with trigol bis aldehyde were prepared and characterized by microanalysis, 1H NMR, UV/Vis. spectroscopy, optical rotation and mass spectroscopy. Highly enantioselective nitroaldol reaction of various aromatic and aliphatic aldehydes with nitromethane in presence of several bases were carried out in the presence of in situ generated Cu(I)/Cu(II) complexes with chiral macrocyclic salen ligands 1′-3′ at RT. Excellent yields (up to 92% with respect to the aldehyde) of β-nitroalcohols with high enantioselectivity (ee, ～95%) was achieved in case of 3-methoxy- and 4-nitrobenzaldehyde in ca. 30 h with the use of chiral macrocyclic salen ligands 3′ with CuCl2· 2H2O in presence of 2,6-lutidine as a base. Chiral macrocyclic salen catalyst 3 mediated nitroaldol process is recyclable (up to 8 cycles with no significant loss in its performance). This protocol is also used for the synthesis of enantiomerically pure (R)-phenylephrine (α1-adrenergic receptor agonist) via asymmetric nitroaldol reaction of 3-methoxybenzaldehyde in three steps.

Methylcarbonate and bicarbonate phosphonium salts as catalysts for the nitroaldol (Henry) reaction

Phosphonium ionic liquids exchanged with bicarbonate and methylcarbonate anions (CILs) exhibit catalytic performances comparable to those of sterically hindered (non nucleophilic) organosuperbases such as DBU. At 25-50 °C, under solventless conditions, CI