216064-48-1

Basic information

• Product Name: TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• Synonyms: TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE;2-tert-butyloxycarbonyl-5-hydroxy-1,2,3,4-tetrahydroisoquinoline;N-BOC-1,2,3,4-tetrahydro-5-hydeoxy-isoquinoline;5-Hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester;2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-5-hydroxy-, 1,1-dimethylethyl ester
• CAS NO: 216064-48-1
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• EINECS: 200-258-5
• Mol File: 216064-48-1.mol

Chemical Properties

• Boiling Point: 378.561 °C at 760 mmHg
• Flash Point: 182.747 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• PKA: 9.96±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(216064-48-1)
• EPA Substance Registry System: TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(216064-48-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 216064-48-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
TERT-BUTYL 5-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE is used as a synthetic intermediate for various organic chemistry reactions. Its isoquinoline structure and functional groups make it a valuable compound in the synthesis of more complex molecules and pharmaceuticals. The tert-butyl group's steric bulk and the hydroxy group's acidity contribute to its reactivity and potential applications in the development of new chemical entities.

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

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 102879-34-5 5-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 102877-50-9 1,2,3,4-tetrahydro-5-hydroxy-isoquinoline 
• 2439-04-5 5-hydroxyisoquinoline 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 441065-33-4 5-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 853076-94-5 5-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid propyl ester 
• 853076-92-3 5-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 918411-15-1 8-(2-methoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid prop-2-ynyl ester 

Relevant articles and documents

Synthesis and biological evaluation of 1,2,3,4-tetrahydroisoquinoline derivatives as potent and selective M2 muscarinic receptor antagonists

A series of 1,2,3,4-tetrahydroisoquinoline derivatives containing the 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one skeleton were prepared and evaluated for their in vitro binding affinities to muscarinic receptors and for antagonism of bradycardia in vivo. Among them, compound 3f had the highest affinity for M2 muscarinic receptors in the heart (pKi=9.1) with low affinity for M3 muscarinic receptors in the submandibular gland. A structure-activity relationship (SAR) study suggested that the benzene ring fused piperidine and the alkyl linker chain length are crucially important for increased M2 affinity.

A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction

A hydroxymethylated polystyrene resin has been converted to its vinylsulfonylethyl ether (1) by DBU catalyzed addition of the hydroxy groups to divinyl sulfone. The support obtained was used to convert 5- and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5- and 6-alkoxy substituents (5a-m). The synthesis involved attachment of the starting material to the support by Michael addition, acid-catalyzed removal of the tetrahydropyranyl protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine.

NOVEL MACROCYCLIC DERIVATIVES, PROCESS FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

Compound of formula (I): wherein A1, A2, Ra, Rb, Rc, Rd, R3, R4, X, Y and G are as defined in the description, and their use in the manufacture of medicaments.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

ANTIMICROBIAL COMPOUNDS, COMPOSITIONS AND METHODS

The invention discloses compounds of the formula wherein A, B, X, Y and Z are defined. The compounds of the invention show activity against a range of bacteria, and are useful in the treatment or prophylaxis of a bacterial infection in an animal.

PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.

Tetrahydroisoquinoline PPARγ agonists: Design of novel, highly selective non-TZD antihyperglycemic agents

Novel tetrahydroisoquinolines have been developed as potent PPAR ligands. Evaluation of these compounds in PPARγ responsive models of type 2 diabetes is described.

Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles

The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction.

HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREATMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR

The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

AROMATIC AMINE DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND AGENTS CONTAINING THE SAME

Compounds of a formula: wherein Ring A represents an optionally-substituted aromatic ring; Ring B represents an optionally-substituted cyclic hydrocarbon group; Z represents an optionally-substituted cyclic group; R1 represents a hydrogen atom, an optionally-substituted hydrocarbon group, an optionally-substituted heterocyclic group, or an acyl group; R2 represents an optionally-substituted amino group; D represents a chemical bond or a divalent group; E represents -CO-, -CON(Ra)-, COO-, -N(Ra)CON(Rb)-, -N(Ra)COO-, -N(Ra)SO2-, -N(Ra)-, -O-, -S-,-SO- or -SO2- (in which Ra and Rb each independently represent a hydrogen atom or an optionally-substituted hydrocarbon group); G represents a chemical bond or a divalent group; L represents (1) a chemical bond or (2) a divalent hydrocarbon group optionally having from 1 to 5 substituents selected from;(i) a C1-6 alkyl group,(ii) a halogeno-C1-6 alkyl group,(iii) a phenyl group,(iv) a benzyl group,(v) an optionally-substituted amino group,(vi) an optionally-substituted hydroxy group, and(vii) a carbamoyl or thiocarbamoyl group optionally substituted by: a C1-6 alkyl group, an optionally-substituted phenyl group, or an optionally-substituted heterocyclic group, and optionally interrupted by -O- or -S-; X represents an oxygen atom, an optionally-oxidized sulfur atom, an optionally-substituted nitrogen atom, or an optionally-substituted divalent hydrocarbon group; Y represents two hydrogen atoms, an oxygen atom or a sulfur atom; .... means that R2 may be bonded to the atom on Ring B to form a ring, or their salts, and a method for producing them.