50341-99-6

Basic information

• Product Name: 1-Naphthalenecarbonyl chloride, 1,2,3,4-tetrahydro-
• CAS NO: 50341-99-6
• Molecular Formula: C11H11ClO
• Molecular Weight: 194.661
• Mol File: 50341-99-6.mol

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenecarbonyl chloride, 1,2,3,4-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenecarbonyl chloride, 1,2,3,4-tetrahydro-(50341-99-6)
• EPA Substance Registry System: 1-Naphthalenecarbonyl chloride, 1,2,3,4-tetrahydro-(50341-99-6)

Safety Data

• Hazardous Substances Data: 50341-99-6(Hazardous Substances Data)

Usage

Appearance

White to light yellow crystalline solid

Uses

Production of pharmaceuticals and agrochemicals

Reactivity

Reactive intermediate used to introduce the naphthalene carbonyl group into various organic molecules

Importance

Building block in the synthesis of pharmaceuticals and other advanced materials, valuable tool in medicinal chemistry and chemical synthesis.

Upstream product

• 1914-65-4 tetralin-1-carboxylic acid 

Downstream Products

• 94540-41-7 phenyl(1,2,3,4-tetrahydronaphthalen-1-yl)methanone 
• 1401467-17-1 diethyl (E)-cinnamyloxy(3,4-dihydronaphthalen-1(2H)-ylidene)methylphosphonate 
• 1459789-80-0 N-(2-bromophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxamide 
• 1459789-82-2 N-(2-bromo-4-methylphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxamide 
• 1459789-83-3 N-(2-bromo-4-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxamide 
• 1459789-84-4 N-(2-bromo-4-fluorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxamide 
• 177793-80-5 C₁₈H₂₆N₂ 
• 135755-51-0 palonosetron hydrochloride 
• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide 

Relevant articles and documents

Palladium-Catalyzed Migratory Insertion of Carbenes and C-C Cleavage of Cycloalkanecarboxamides

A palladium catalyzed reaction of cycloalkanecarboxamides and diazomalonates or bis(phenylsulfonyl)diazomethane has been developed. The reaction proceeds via carbene migratory insertion and cascade C-C cleavage pathways. Cycloalkanecarboxamides with four to seven membered rings are applicable in the transformation. A series of ring opening products were prepared with moderate yields. The finding provides valuable clues for the development of new reactions involving carbene migratory insertion and the cleavage of unstrained C(sp3)-C(sp3) bonds.

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2-Amino Acids

The asymmetric synthesis of β2,2-amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2-amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2-amino acids has been developed.

Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.

A hydrochloric acid palonosetron synthesis method

The invention relates to a new synthetic method of palonosetron hydrochloride, and belongs to the field of pharmaceutical organic synthesis. The synthetic method adopts racemized tetrahydro naphthoic acid as a raw material; a reaction is carried out with thionyl chloride and (S)-3-aminoquinuclidine; after repeated washing, (S,S)-quinuclidine tetrahydronaphthalene carboxamide is obtained; the amide is reacted with sodium borohydride and boron trifluoride diethyl etherate; the product is added into a hydrochloric acid aqueous solution to obtain the palonosetron hydrochloride. According to the method, in the amide synthetic process, ethyl acetate is used as a solvent, which reduces the generation of by-products. In addition, according to the method, in the post-treatment process, impurities are removed by phase transfer, which increases product optical purity; through repeated washing, other impurities generated in the reaction are removed, and high-purity product is obtained.

Origins of diastereoselectivity in lewis acid promoted ketene-alkene [2 + 2] cycloadditions

A detailed analysis of a Lewis acid promoted ketene-alkene [2 + 2] cycloaddition is reported. The studies have led to a rationalization for an observed inversion of diastereoselectivity between thermally induced and Lewis acid promoted ketene-alkene [2 + 2] cycloadditions. The model is supported with both experimental and computational results.

Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions

Described are the first examples of ketene-alkene [2 + 2] cycloadditions promoted by Lewis acids. Notable features of this method include (1) substantial rate acceleration relative to traditional thermal reactions, (2) good diastereoselectivities and yields for the formation of the cyclobutanone products, and (3) inverse diastereoselectivity compared with related thermal cycloadditions for many examples. These studies not only provide access to synthetically versatile cyclobutanones that cannot be prepared by traditional thermal cycloadditions but also address important mechanistic questions regarding ketene-alkene [2 + 2] cycloaddition reactions.

Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed asymmetric intramolecular α-arylation of amides: Reaction development and mechanistic studies

Palladium complexes incorporating chiral N-heterocyclic carbene (NHC) ligands catalyze the asymmetric intramolecular α-arylation of amides producing 3,3-disubstituted oxindoles. Comprehensive DFT studies have been performed to gain insight into the mechanism of this transformation. Oxidative addition is shown to be rate-determining and reductive elimination to be enantioselectivity-determining. The synthesis of seven new NHC ligands is detailed and their performance is compared. One of them, L8, containing a tBu and a 1-naphthyl group at the stereogenic centre, proved superior and was very efficient in the asymmetric synthesis of fifteen new spiro-oxindoles and three azaspiro-oxindoles often in high yields (up to 99 %) and enantioselectivities (up to 97 % ee; ee=enantiomeric excess). Three palladacycle intermediates resulting from the oxidative addition of [Pd(NHC)] into the aryl halide bond were isolated and structurally characterized (X-ray). Using these intermediates as catalysts showed alkene additives to play an important role in increasing turnover number and frequency. Copyright

Asymmetric pericyclic cascade approach to spirocyclic oxindoles

The reaction of chiral N-arylnitrones with carbocyclic alkylarylketenes generates spirocyclic oxindoles in good yields and with excellent levels of enantioselectivity (90-99% ee) via a pericyclic cascade process.

Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups. Copyright

Aza-oxindole synthesis via base promoted Truce-Smiles rearrangement

A novel efficient NaOtBu-mediated protocol for the synthesis of 3,3-disubstituted aza-oxindoles proceeds via a Truce-Smiles rearrangement- cyclisation pathway.