158984-83-9

Basic information

• Product Name: TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• Synonyms: TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE;6-HYDROXY-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER;5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate;N-BOC-6-HYDROXY-3,4-DIHYDRO-ISOQUINOLINE;6-hydroxy-2-N-Boc-3,4-dihydroisoquinoline;tert-Butyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;tert-Butyl 6-hydroxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate;2-N-Boc-6-Hydroxy-3,4-dihydroisoquinoline
• CAS NO: 158984-83-9
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Mol File: 158984-83-9.mol

Chemical Properties

• Melting Point: 110-111.5 °C
• Boiling Point: 391.376 °C at 760 mmHg
• Flash Point: 190.497 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• PKA: 9.79±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(158984-83-9)
• EPA Substance Registry System: TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(158984-83-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 158984-83-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate is used as a chemical reagent for the synthesis of androgen receptor modulators. Its role in the pharmaceutical industry is crucial, as it aids in the development of medications that can potentially treat various conditions related to androgen receptors, such as hormonal imbalances and certain types of cancer.
Used in Research and Development:
In addition to its application in the pharmaceutical industry, tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate is also utilized in research and development settings. Scientists and researchers employ tert-Butyl 6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate to study the mechanisms of androgen receptor modulators and to develop new drugs with improved efficacy and safety profiles.

InChI:InChI=1/C14H19NO3/c1-14(2,3)18-13(17)15-7-6-10-8-12(16)5-4-11(10)9-15/h4-5,8,16H,6-7,9H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7651-82-3 isoquinolin-6-ol 
• 22246-12-4 6-methoxy-1,2,3,4-tetrahydro-1-oxoisoquinoline 
• 42923-77-3 6-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 110192-21-7 N-(methoxycarbonyl)-2-(3'-methoxyphenyl)ethylamine 
• 942150-85-8 bis(6-methoxy-N-1,2,3,4-tetrahydroisoquinolinyl)methane 
• 57196-62-0 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 3179-09-7 1-methoxy-3-(2-nitrovinyl)benzene 
• 591-31-1 3-methoxy-benzaldehyde 
• 110339-52-1 C₁₀H₁₃NO 
• 110-89-4 piperidine 
• 59839-23-5 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide 
• 14446-24-3 6-hydroxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1266120-56-2 6-(4-tert-butyl-cyclohexyloxy)-1,2,3,4-tetrahydro-isoquinoline hydrochloride 
• 1266120-58-4 3-tert-butoxycarbonylamino-4-[6-(4-tert-butyl-cyclohexyloxy)-3,4-dihydro-1H-isoquinolin-2-yl]-4-oxo-butyric acid tert-butyl ester 
• 1266120-54-0 6-(4-tert-butyl-cyclohexyloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 164148-88-3 6-benzyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 252061-94-2 6-benzyloxy-1,2,3,4-tetrahydro-isoquinoline 
• 630407-52-2 6-ethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 1429254-04-5 C₂₄H₂₅N₃O₃ 
• 1429253-97-3 C₂₈H₂₆N₄O₂ 
• 893566-72-8 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 158984-84-0 6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 1046816-76-5 tert-butyl 6-(3-(4-(5-ethylpyrimidin-2-yl)phenyl)propoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant articles and documents

An improved procedure for the cyanation of aryl triflates: A convenient synthesis of 6-cyano-1,2,3,4-tetrahydroisoquinoline

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A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

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SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS USEFUL AS GPR120 AGONISTS

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Design and synthesis of novel androgen receptor antagonists via molecular modeling

Several androgen receptor (AR) antagonists are clinically prescribed to treat prostate cancer. Unfortunately, many patients become resistant to the existing AR antagonists. To overcome this, a novel AR antagonist candidate called DIMN was discovered by our research group in 2013. In order to develop compounds with improved potency, we designed novel DIMN derivatives based on a docking study and substituted carbons with heteroatom moieties. Encouraging in vitro results for compounds 1b, 1c, 1e, 3c, and 4c proved that the new design was successful. Among the newly synthesized compounds, 1e exhibited the strongest inhibitory effect on LNCaP cell growth (IC50= 0.35 μM) and also acted as a competitive AR antagonist with selectivity over the estrogen receptor (ER) and the glucocorticoid receptor (GR). A docking study of compound 1e fully supported these biological results. Compound 1e is considered to be a novel, potent and AR-specific antagonist for treating prostate cancer. Thus, our study successfully applied molecular modeling and bioisosteric replacement for hit optimization. The methods here provide a guide for future development of drug candidates through structure-based drug discovery and chemical modifications.

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