118864-75-8

Basic information

• Product Name: (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (S)-1,2,3,4- four-1- phenylhydrogenisoquinoline;Solifenacin Succinate interMediate F;Solifenacin Related Compound 11;(S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline;(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline, Solifenacin intermediate;Solifenacin Impurity A;(S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline,99%e.e.;(S)-1,2,3,4-TETRAHYDRO-1-PHENYLISOQUINOLINE
• CAS NO: 118864-75-8
• Molecular Formula: C₁₅H₁₅N
• Molecular Weight: 209.29
• EINECS: 1806241-263-5
• Product Categories: Other APIs;API intermediates;Aromatics Compounds;Aromatics;Chiral Reagents;Heterocycles;Isotope Labeled Compounds
• Mol File: 118864-75-8.mol
• Article Data: 61

Chemical Properties

• Melting Point: 80-82°C
• Boiling Point: 338°C
• Flash Point: 167°C
• Appearance: white solid
• Density: 1.065
• Vapor Pressure: 9.87E-05mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• PKA: 8.91±0.40(Predicted)
• CAS DataBase Reference: (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline(118864-75-8)
• EPA Substance Registry System: (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline(118864-75-8)

Safety Data

• Hazardous Substances Data: 118864-75-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 118864-75-8 differently. You can refer to the following data:
1. Labelled Solifenacin intermediate
2. Solifenacin (S676700) intermediate.

InChI:InChI=1/C15H15N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9,15-16H,10-11H2/t15-/m0/s1

Upstream product

• 1443308-90-4 N-benzyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1443308-91-5 C₂₂H₁₈N⁽¹⁺⁾*Br^(1-) 
• 3297-72-1 1-phenylisoquinoline 
• 324027-23-8 2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-benzaldehyde 
• 213686-67-0 (+)-N-<(αS)-2-<<(4R,5R)-4,5-bis(2-methoxypropan-2-yl)-1,3-dioxolan-2-yl>methyl>benzhydryl>-4-methylbenzenesulfonamide 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 87-69-4 L-Tartaric acid 
• 660861-57-4 (1S,5R)-5,8,8-trimethyl-1-[(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one 
• 220936-58-3 (S)-(-)-2-(4-methylphenylsulfonyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 172794-79-5 (S)-(-)-benzyl 1-phenyl-1,2-dihydroisoquinoline-2-carboxylate 
• 132283-71-7 (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 98-56-6 4-chlorobenzotrifluoride 
• 119-61-9 benzophenone 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 

Downstream Products

• 862207-71-4 (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate 
• 862207-70-3 (3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate 
• 1262506-09-1 solifenacin succinate 
• 1203447-95-3 phenyl (S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate 
• 1195949-26-8 (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carbonyl chloride 
• 1251905-45-9 methyl (1S)-1-phenyl-3,4-dihydro-2(1H)-isoquinoline-carboxylate 
• 1229227-22-8 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1262506-09-1 (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate 
• 1354548-49-4 1-azabicyclo[2.2.2]oct-8-yl (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate fumarate 
• 1422464-27-4 (S)-N-chloro-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 242478-37-1 solifenacin 
• 180272-31-5 1(S)-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of 1-Aryl-3,4-Dihydroisoquinolines Using a Cp*Ir(TsDPEN) Complex

We report herein a simple alternative method for the asymmetric transfer hydrogenation (ATH) of 1-aryl-3,4-dihydroisoquinolines (1-Ar-DHIQs) that are known to be challenging substrates owing to their poor reactivity. The hydrogenation protocol employs the

The development of an asymmetric hydrogenation process for the preparation of solifenacin

The successful development of a catalytic imine asymmetric hydrogenation process for the reduction of the hydrochloride salt of 1-phenyl-3,4- dihydroisoquinoline to 1-(S)-phenyl-1,2,3,4-tetrahydroisoquinoline is described. This represents a novel approach to the key intermediate in preparing the urinary antispasmodic drug solifenacin, (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl-3, 4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate. Suitable reaction conditions were identified through an extensive screen of catalysts and combination of solvents and additives. The best reaction conditions: [Ir(COD)Cl] 2-(S)-P-Phos, molar substrate to catalyst ratio (S/C) of >1000/1, THF, 1-2 equiv of H3PO4, 60 °C, 20 bar H2, were reproduced on a 200 g scale (95% isolated yield, 98% ee and >99% HPLC product purity).

Enantioselective synthesis of 1-Aryl-substituted tetrahydroisoquinolines employing imine reductase

Tetrahydroisoquinolines (THIQs) with a C1-aryl-substituted groups are common in many natural and synthetic compounds of biological importance. Currently, their enantioselective synthesis are primarily reliant on chemical catalysis. Enzymatic synthesis using imine reductase is very attractive, because of the cost-effectiveness, high catalytic efficiency, and enantioselectivity. However, the steric hindrance of the 1-aryl substituents make this conversion very challenging, and current successful examples are mostly restricted to the simple alkyl-THIQs. In this report, through extensive evaluation of a large collection of IREDs (including 88 enzymes), we successfully identified a panel of steric-hindrance tolerated IREDs. These enzymes are able to convert meta- and para-substituted chloro-, methyl-, and methoxyl-benzyl dihydroisoquinolines (DHIQs) into corresponding R- or S- THIQs with very high enantioselectivity and conversion. Among them, the two most hindrance-tolerated enzymes (with different stereospecificity) are also able to convert ortho-substituted chloro-, methyl-, and methoxyl-benzyl DHIQs and dimethoxyl 1-chlorobenzyl-DHIQs with good enantiometric excess. Furthermore, using in silico modeling, a highly conserved tryptophan residue (W191) was identified to be critical for substrate accommodation in the binding cavity of the S-selective IRED (IR45). Replacing W191 with alanine can dramatically increase the catalytic performance by decreasing the Km value by 2 orders of magnitude. Our results provide an effective route to synthesize these important classes of THIQs. Moreover, the disclosed sequences and substrate binding model set a solid basis to generate more-efficient and broad-selective enzymes via protein engineering.

Ferritin encapsulation of artificial metalloenzymes: Engineering a tertiary coordination sphere for an artificial transfer hydrogenase

Ferritin, a naturally occuring iron-storage protein, plays an important role in nanoengineering and biomedical applications. Upon iron removal, apoferritin was shown to allow the encapsulation of an artificial transfer hydrogenase (ATHase) based on the streptavidin-biotin technology. The third coordination sphere, provided by ferritin, significantly influences the catalytic activity of an ATHase for the reduction of cyclic imines.

Low-Temperature Nickel-Catalyzed C?N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand

The transition-metal-catalyzed C?N cross-coupling has revolutionized the construction of amines. Despite the innovations of multiple generations of ligands to modulate the reactivity of the metal center, ligands for the low-temperature enantioselective amination of aryl halides remain a coveted target of catalyst engineering. Designs that promote one elementary reaction often create bottlenecks at other steps. We here report an unprecedented low-temperature (as low as ?50 °C), enantioselective Ni-catalyzed C?N cross-coupling of aryl chlorides with sterically hindered secondary amines via a kinetic resolution process (s factor up to >300). A bulky yet flexible chiral N-heterocyclic carbene (NHC) ligand is leveraged to drive both oxidative addition and reductive elimination with low barriers and control the enantioselectivity. Computational studies indicate that the rotations of multiple σ-bonds on the C2-symmetric chiral ligand adapt to the changing needs of catalytic processes. We expect this design would be widely applicable to diverse transition states to achieve other challenging metal-catalyzed asymmetric cross-coupling reactions.

Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity

The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.

Synthesis method of (S)-1-phenyl-1, 2, 3, 4-tetrahydroisoquinoline

The invention relates to a synthetic method of (S) 1-phenyl -1, 2, 3, 4-tetrahydroisoquinoline. The method comprises the following steps: mixing 1-phenyl-3, 4-dihydroisoquinoline, a chiral catalyst, an acid and a solvent, and reacting, wherein the structural formula of the chiral catalyst is shown as a formula (I). further forming (S)-1phenyl -1, 2, 3, 4-tetrahydroisoquinoline with high chiral purity in one step in the hydrogenation reduction process, meanwhile, the product is easy to separate and purify, and the yield is high. In addition, the invention is mild in reaction condition, stable in process, simple, convenient and safe in reaction operation, low in production cost, simple and feasible in three-waste treatment, environment-friendly, simple in equipment used in the reaction process, easily available in raw materials, low in production cost and suitable for industrial production.