1914-65-4

Basic information

• Product Name: 1,2,3,4-Tetrahydro-1-naphthoic acid
• Synonyms: 1,2,3,4-TETRAHYDRO-1-NAPHTHOIC ACID;1,2,3,4-TETRAHYDRO-NAPHTHALENE-1-CARBOXYLIC ACID;1,2,3,4-TETRAHEDRO-NAPHTHOIC ACID;1-Tetralincarboxylic acid;1,2,3,4-TETRAHYDRO-1-NAPHTHOIC;1,2,3,4-tetrahydro-naphthoic acid;1-Naphthalenecarboxylicacid, 1,2,3,4-tetrahydro;1,2,3,4-Tetrahydro-1-naphtholic acid
• CAS NO: 1914-65-4
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• EINECS: 1806241-263-5
• Product Categories: Pharmaceutical material and intermeidates;Benzocycles;INTERMEDIATESOFPALONOSETRONHYDROCHLORIDE;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1914-65-4.mol

Chemical Properties

• Melting Point: 75-77°C
• Boiling Point: 135°C/5mmHg(lit.)
• Flash Point: 156.408 °C
• Appearance: /
• Density: 1.186 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Refrigerator
• Solubility: Soluble in methanol, and chloroform.
• PKA: 4.28±0.20(Predicted)
• CAS DataBase Reference: 1,2,3,4-Tetrahydro-1-naphthoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydro-1-naphthoic acid(1914-65-4)
• EPA Substance Registry System: 1,2,3,4-Tetrahydro-1-naphthoic acid(1914-65-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-51
• Safety Statements: 26
• Hazardous Substances Data: 1914-65-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3,4-Tetrahydro-1-naphthoic acid is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new materials and products.
Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-1-naphthoic acid is used as a reagent to produce protease inhibitors, which are crucial in the treatment of various diseases and conditions by inhibiting the activity of proteases.
Used in Agrochemicals:
1,2,3,4-Tetrahydro-1-naphthoic acid is utilized as a vital component in the development of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Used in Dyestuff Industry:
1,2,3,4-Tetrahydro-1-naphthoic acid is employed as a raw material in the production of dyes, contributing to the creation of a wide range of colors and pigments for various applications.

InChI:InChI=1/C11H12O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7H2,(H,12,13)

Upstream product

• 132205-64-2 1-cyanotetraline 
• 86-55-5 1-naphthalenecarboxylic acid 
• 5111-73-9 1,4-dihydro-1-naphthalenecarboxylic acid 
• 3333-23-1 3,4-dihydronaphthalene-1-carboxylic acid 
• 19692-24-1 4-ethoxy-1-naphthoic acid 
• 16827-42-2 (+/-)-1,2-dihydro-[1]naphthoic acid 
• 17502-86-2 Methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 71-41-0 pentan-1-ol 
• 826-73-3 1-Benzosuberone 
• 7770-45-8 4-hydroxy-1-naphthaldehyde 
• 93340-32-0 3,4-dihydro-1-naphthalenecarboxaldehyde 
• 91064-96-9 2,3,4-Trichlor-naphthoesaeure 
• 3123-46-4 4-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 124-38-9 carbon dioxide 

Downstream Products

• 86346-43-2 1,2,3,4-tetrahydro-[2]naphthoyl chloride 
• 66041-55-2 1,2,3,4-tetrahydro-[1]naphthoic acid ethyl ester 
• 85977-52-2 (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 23357-47-3 (R)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 50341-99-6 1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride 
• 104116-25-8 4-bromo-1,2,3,4-tetrahydro-[1]naphthoic acid 
• 7384-42-1 decalin-1-carboxylic acid 
• 107424-67-9 1,2,3,4-tetrahydro-1-naphthalenecarboxylic acid phenyl ester 
• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ylcarboxamide 
• 405102-98-9 N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide 
• 17502-86-2 Methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 25634-94-0 (1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanol 
• 66377-63-7 (1,2,3,4-tetrahydronaphthalen-4-yl)methanol 
• 113967-23-0 methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate 

Relevant articles and documents

Method for preparing 1,2,3,4-tetrahydro-1-naphthoic acid by using superstrong alkali method

The invention discloses a method for preparing 1,2,3,4-tetrahydro-1-naphthoic acid by using a superstrong alkali method. The method comprises the following steps: (1) under the protection of nitrogen,preparing a hydrogen drawing product by using tetrahydronaphthalene as a raw material, adding potassium tert-butoxide, using n-hexane as a solvent and dropwisely adding n-butyllithium; and (2) underthe protection of nitrogen, introducing dry carbon dioxide into the system, and acidifying to obtain the target product, wherein in the step (1), a molar ratio of potassium tert-butoxide to n-butyllithium is 1:(0.5-1.5), preferably 1:1.0, and preferably in the step (1), a molar ratio of the superstrong alkali to the tetrahydronaphthalene is 1:(0.5-2), preferably 1:(1.2-1.5). Compared with the method in the prior art, the method of the invention has the advantages of short steps, cheap raw materials, high yield, high operability, good repeatability and convenience in industrialization.

Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions

A range of hitherto unexplored biomass-derived chemicals have been evaluated as new sustainable solvents for a large variety of CO2-based carboxylation reactions. Known biomass-derived solvents (biosolvents) are also included in the study and the results are compared with commonly used solvents for the reactions. Biosolvents can be efficiently applied in a variety of carboxylation reactions, such as Cu-catalyzed carboxylation of organoboranes and organoboronates, metal-catalyzed hydrocarboxylation, borocarboxylation, and other related reactions. For many of these reactions, the use of biosolvents provides comparable or better yields than the commonly used solvents. The best biosolvents identified are the so far unexplored candidates isosorbide dimethyl ether, acetaldehyde diethyl acetal, rose oxide, and eucalyptol, alongside the known biosolvent 2-methyltetrahydrofuran. This strategy was used for the synthesis of the commercial drugs Fenoprofen and Flurbiprofen.

Electrogenerated Sm(II)-Catalyzed CO2 Activation for Carboxylation of Benzyl Halides

Sm(II)-catalyzed carboxylation of benzyl halides is reported through the electrochemical reduction of CO2. The transformation proceeds under mild reaction conditions to afford the corresponding phenylacetic acids in good to excellent yields. This user-friendly and operationally simple protocol represents an alternative to traditional strategies, which usually proceeds through the C(sp3)-halide activation pathway.

Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: Scope and mechanistic insights

A caesium fluoride-mediated hydrocarboxylation of olefins is disclosed that does not rely on precious transition metal catalysts and ligands. The reaction occurs at atmospheric pressures of CO2 in the presence of 9-BBN as a stoichiometric reductant. Stilbenes, β-substituted styrenes and allenes could be carboxylated in good yields. The developed methodology can be used for preparation of commercial drugs as well as for gram scale hydrocarboxylation. Computational studies indicate that the reaction occurs via formation of an organocaesium intermediate.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.

Method for preparing (S)-tetrahydro-1-naphthoic acid through high-efficiency resolution

The invention relates to a preparation method of a palonosetron hydrochloride key intermediate (S)-1,2,3,4-tetrahydro-1-naphthoic acid as shown in a formula (I). The method comprises the following steps of adding a resolution agent for resolution by adopting 1,2,3,4-tetrahydro-naphthalene acid racemate as a raw material to obtain a salt (III) formed by a (S)-1,2,3,4-tetrahydro naphthalene acid and the resolution agent, and a salt (IV) formed by (R)-1,2,3,4-tetrahydro naphthalene acid and the resolution agent; carrying out salt removing on a compound III and a compound IV separately to obtain compounds (I) and (II); and carrying out racemization on the compound (II) under an alkaline condition to obtain a starting material 1,2,3,4-tetrahydro-naphthalene acid racemate and further carrying out resolution according to the steps. Therefore, the overall yield can be greatly improved, the production cost is reduced and environmental protection is facilitated. The preparation technology of the palonosetron hydrochloride key intermediate provided by the invention is different from the prior art, is safe, environmentally friendly, simple in operation and high in yield, and has relatively great practical value. The formula is as shown in the specification.

ALLOSTERIC BINDING COMPOUNDS

The present invention relates to allosteric binding compounds of formula (I), especially for the treatment of CNS disorders, together with pharmaceutical compositions and methods of treatment including these compounds.

Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber

The full-structure of a norlabdane terpenoid, kujigamberol (1) was determined by total synthesis. Key features of the total synthesis are (1) installation of isopentyl group through an o-lithiation of benzamide, (2) construction of tetralone by the RCM reaction, and (3) optical resolution of (±)-1 using chromatographical separation of the corresponding camphanates. X-ray crystallographical analysis of p-bromobenzoate obtained from the more polar camphanate that was identical with a natural derivative, revealed natural kujigamberol to have an S-configuration. Both the natural enantiomer and its (R)-antipode showed the same inhibitory activity toward the mutant yeast and HL-60 cells, while simple analogs without alkyl groups at the C-8 and 9 positions of (±)-1 had no such activity.

Hydroxide ion as electron source for photochemical Birch-type reduction and photodehalogenation

The photochemical Birch-type reduction of arenes and the photodehalogenation of haloarenes by a hydroxide ion that acted as an electron source occurred in 2-PrOH. The efficiency of these photoreactions was dependent on the nature of the substrate, the concentration of NaOH, and the solvent used. These photoreactions provide an environmentally friendly method for the reduction of aromatic rings and dehalogenation.

A novel synthetic route to 2-arylalkanoic acids by a ruthenium-catalyzed chemoselective oxidation of furan rings

An efficient two-step synthesis of 2-arylalkanoic acids from 1-arylalkanols is described. Firstly, 1-arylalkylfuran derivatives were synthesized in high yields by the metal triflate catalyzed Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H2O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl3 as catalyst to give 2-arylalkanoic acids in good yields. The selectivity of ruthenium oxidation was controlled by the solvent ratio of hexane-EtOAc. Georg Thieme Verlag Stuttgart.