104576-30-9

Basic information

• Product Name: 7-CHLORO-1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE
• Synonyms: 7-CHLORO-1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE
• CAS NO: 104576-30-9
• Molecular Formula: C₁₅H₁₂ClN
• Molecular Weight: 241.71548
• Mol File: 104576-30-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-CHLORO-1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE(104576-30-9)
• EPA Substance Registry System: 7-CHLORO-1-PHENYL-3,4-DIHYDRO-ISOQUINOLINE(104576-30-9)

Safety Data

• Hazardous Substances Data: 104576-30-9(Hazardous Substances Data)

Upstream product

• 3418-95-9 1-(benzoylamino)-2-(4-chlorophenyl)ethane 
• 98-88-4 benzoyl chloride 
• 22245-95-0 7-chloro-1,2,3,4-tetrahydroisoquinolin-1-one 
• 439116-78-6 tert-butyl 7-chloro-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 100-58-3 phenylmagnesium bromide 
• 741615-46-3 7-chloro-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 156-41-2 4-chlorophenylethylamine 

Downstream Products

• 741615-46-3 7-chloro-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 104576-35-4 2-acetyl-1,1,5-trichloro-3-phenyl-1a,2,3,7b-tetrahydro-1H-cyclopropisoquinoline 
• 104576-37-6 1-((1aR,3S,7bS)-1,1-Dibromo-5-chloro-3-phenyl-1,1a,3,7b-tetrahydro-2-aza-cyclopropa[a]naphthalen-2-yl)-ethanone 
• 104576-40-1 4-Bromo-8-chloro-1-phenyl-5H-benzo[c]azepine 
• 126115-23-9 2-benzyl-7-chloro-1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 104576-33-2 N-acetyl-7-chloro-1-phenyl-1,2-dihydroisoquinoline 

Relevant articles and documents

One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.

Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues

A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.

Aromatic ring or fused heterocycle linked 3,4-dihydroisoquinoline conjugated structure compound and application thereof

The invention discloses an aromatic ring or fused heterocycle linked 3,4-dihydroisoquinoline conjugated structure compound and application thereof. The structure of the aromatic ring or fused heterocycle 3,4-dihydroisoquinoline conjugated structure compound is as shown in the formula II, wherein R1 and R2 are independent of each other and are H, C1-C4 alkyl groups, C1-C4 alkoxy groups, F and Cl; R3 and R4 are independent of each other and are H and F or C1-C4 alkyl groups substituted by F; at least one of R1, R2, R3 and R4 is F or Cl or C1-C4 alkyl groups substituted by F; or R3 and R4 are cyclized to form oxygen heterocycles substituted by F. The invention provides application of the aromatic ring or fused heterocycle 3,4-dihydroisoquinoline conjugated structure compound to preparation of monoamine oxidase (MAO) inhibition agents. The compound has a remarkable inhibition function on monoamine oxidase. Please see the chemical structural formula of the compound in the specification.

Palladium carbon catalyzed selective partial dehydrogenation method of tetrahydroisoquinoline

The invention relates to a method for synthesis of 1-substituted-3, 4-dihydroisoquinoline by palladium carbon catalyzed selective partial dehydrogenation of a 1-substituted-1, 2, 3, 4-tetrahydroisoquinoline compound. The reaction temperature is 0-80DEG C. For easily available cyclic amine compounds like tetrahydroisoquinoline, a corresponding imine compound can be obtained through selective dehydrogenation, the conversion rate is up to 99%, and the proportion of a partial dehydrogenation product and a complete dehydrogenation product is greater than 20:1. The method provided by the invention has simple and practical operation, the raw materials and catalyst are cheap and easily available, the reaction conditions are mild, and the catalyst can be recycled, thus greatly reducing the actual cost. In addition, the method for synthesis of 3, 4-dihydroisoquinoline through direct dehydrogenation of tetrahydroisoquinoline has the advantages of atom economy and environmental friendliness.

Solvent-promoted highly selective dehydrogenation of tetrahydroisoquinolines without catalyst and hydrogen acceptor

An unusual solvent DMF-promoted dehydrogenation of 1-substituted 1,2,3,4-tetrahydroisoquinolines to synthesize cyclic imines is described. This environmentally friendly reaction features no requirement of any metal catalysts, oxidants, or hydrogen acceptors. A wide range of structurally varied 3,4-dihydroisoquinolines can be obtained with good yields and excellent chemoselectivities.

Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K3PO4·3H2O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K3PO4·3H2O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology.

Ionic liquids-assisted synthesis of 3,4-dihydroisoquinolines by the Bishler-Napieralski reaction

The Bishler-Napieralski cyclodehydration of N-acyl-2-arylethylamines into the corresponding 3,4-dihydroisoquinolines with POCl3 as a dehydration reagent proceeds in ionic liquids under milder conditions and in higher yields.

Structure-activity relationship studies of novel benzophenones leading to the discovery of a potent, next generation HIV nonnucleoside reverse transcriptase inhibitor

Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.