(1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

  • CAS:118864-75-8
  • MF:C15H15N
  • Purity:99%
  • Molecular Weight:209.291
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Product Details

  • CAS: 118864-75-8
  • MF: C15H15N
  • Appearance: white solid
  • Manufacturer supply top purity (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline 118864-75-8 with ISO standards

    • Molecular Formula:C15H15N
    • Molecular Weight:209.291
    • Appearance/Colour:white solid 
    • Vapor Pressure:9.87E-05mmHg at 25°C 
    • Melting Point:80-82 °C 
    • Refractive Index:1.589 
    • Boiling Point:338.4 °C at 760 mmHg 
    • PKA:8.91±0.40(Predicted) 
    • Flash Point:167 °C 
    • PSA:12.03000 
    • Density:1.065 g/cm3 
    • LogP:3.25050 

    (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline(Cas 118864-75-8) Usage

    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

    118864-75-8 Relevant articles

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

    Václavíková Vilhanová, Bea,Budinská, Alena,Václavík, Ji?í,Matou?ek, Václav,Kuzma, Marek,?erveny, Libor

    , p. 5131 - 5134 (2017)

    We report herein a simple alternative me...

    Stereoselective Total Syntheses of Solifenacin and N -Acetyl-1-(4-chloro-phenyl)-6,7-dimethoxytetrahydroisoquinoline

    Babu, R. Anji,Reddy, N. Siva Senkar,Reddy, B. Jagan Mohan,Reddy, B. V. Subba

    , p. 2794 - 2798 (2014)

    A highly stereoselective synthesis of 1-...

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

    Ruzic, Milos,Pecavar, Anica,Prudic, Darja,Kralj, David,Scriban, Corina,Zanotti-Gerosa, Antonio

    , p. 1293 - 1300 (2012)

    The successful development of a catalyti...

    Directed evolution of artificial metalloenzymes: Genetic optimization of the catalytic activity

    Hestericová, Martina

    , p. 189 - 192 (2018)

    Artificial metalloenzymes (ArMs) based o...

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

    Zhu, Jinmei,Tan, Hongqun,Yang, Lu,Dai, Zheng,Zhu, Lu,Ma, Hongmin,Deng, Zixin,Tian, Zhenhua,Qu, Xudong

    , p. 7003 - 7007 (2017)

    Tetrahydroisoquinolines (THIQs) with a C...

    Synthesis and characterization of S(-)1-phenyl-1,2,3,4-tetrahydro isoquinoline acetamide analogues

    Krishna Rao,Surendra Babu,Basaveswara Rao,Keshavi,Sundara Rao,Eswara Prasad,Murthy

    , p. 1035 - 1038 (2017)

    S(-)1-Phenyl-1,2,3,4-tetrahydro isoquino...

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

    Hestericová, Martina,Heinisch, Tillmann,Lenz, Markus,Ward, Thomas R.

    , p. 10837 - 10841 (2018)

    Ferritin, a naturally occuring iron-stor...

    The absolute configuration of (1S)-(+)- and (1R)-(-)1-phenyl-1,2,3,4-tetrahydroisoquinoline. A revision of the literature assignment

    Ludwig, Matthias,Beer, Herbert,Lotter, Hermann,Wanner, Klaus Th.

    , p. 2693 - 2695 (1997)

    The title compounds (S)-(+)-8 and (R)-(-...

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

    Hong, Xin,Shi, Shi-Liang,Wang, Zi-Chao,Xie, Pei-Pei,Xu, Youjun

    supporting information, p. 16077 - 16084 (2021/06/17)

    The transition-metal-catalyzed C?N cross...

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

    Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin

    supporting information, p. 6283 - 6287 (2020/09/02)

    The use of arene/Ru/TsDPEN catalysts bea...

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

    -

    Paragraph 0040-0076, (2020/02/08)

    The invention relates to a (S)1-phenyl-1...

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

    -

    Paragraph 0068; 0073-0075; 0080-0082; 0087-0089; 0094-0096, (2021/01/15)

    The invention relates to a synthetic met...

    118864-75-8 Process route

    1-phenyl-3,4-dihydroisoquinoline
    52250-50-7

    1-phenyl-3,4-dihydroisoquinoline

    (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
    22990-19-8,96719-89-0,118864-75-8

    (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

    (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
    180272-45-1

    (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

    Conditions
    Conditions Yield
    With sodium tetrahydroborate; In ethanol; at 20 ℃; for 60h;
    With hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In tetrahydrofuran; 1,1-dichloroethane; at 20 - 50 ℃; under 22502.3 Torr; Product distribution / selectivity; Inert atmosphere;
    50 % ee
    With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine; In dichloromethane; at 20 ℃; for 24h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Autoclave;
    With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-3,5-diMe-Synphos; hydrogen; In 1,4-dioxane; at 40 ℃; for 18h; under 22502.3 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
    With formic acid; [RuCl(η6-benzene)(1R,2R)-N-(naphthalene-1-sulfonyl)-1,2-diphenylethylenediamine]; triethylamine; In acetonitrile; at 30 ℃; Reagent/catalyst;
    39 % ee
    With (2S,3R)-2-amino-3-hydroxybutanamide; streptavidin biotin-wild type; C42H64Cl4Ir2N6O4S2; In dimethyl sulfoxide; at 30 - 50 ℃; for 18h; pH=7.8; Reagent/catalyst; Overall yield = 96 %; enantioselective reaction;
    63 % ee
    With C42H64Cl4Ir2N6O4S2; D-Phenylalaninamide; In dimethyl sulfoxide; at 30 - 50 ℃; for 18.25h; pH=7.8; Reagent/catalyst; Overall yield = 99 %; enantioselective reaction;
    16 % ee
    With [N-[(1S,2S)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1,3,5-trimethylbenzene]ruthenium; formic acid; triethylamine; In acetonitrile; for 1.16667h; Optical yield = 2 %ee;
    With [N-[(1S,2S)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1,3,5-trimethylbenzene]ruthenium; formic acid; triethylamine; In isopropyl alcohol; at 30 ℃; for 16h; Overall yield = 90 %; enantioselective reaction; Inert atmosphere;
    29 % ee
    With N-[(1S,2S)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium; hydrogen; trifluoroacetic acid; In methanol; at 40 ℃; for 6h; under 11251.1 Torr; Reagent/catalyst; Autoclave; Sealed tube;
    11 % ee
    With hydrogen; In tetrahydrofuran; toluene; at 30 ℃; for 17h; under 45603.1 Torr; Reagent/catalyst; Solvent; enantioselective reaction; Autoclave;
    24 % ee
    With (pentamethylcyclopentadienyl)IrCl[κ2(N,N')-(S,S)-p-toluenesulfonylNCHPhCHPhNH2]; hydrogen; trifluoroacetic acid; In methanol; for 6h; under 11251.1 Torr; stereoselective reaction;
    71 % ee
    With D-glucose; BmGDH; imine reductase from Stackebrandtia nassauensis; NADP; In aq. phosphate buffer; dimethyl sulfoxide; at 30 ℃; for 12h; pH=7; Overall yield = 81 %; Overall yield = 170 mg; enantioselective reaction; Enzymatic reaction;
    51 % ee
    With formic acid; (1,2,3,4,5-pentamethylcyclopentadienyl)Ir[κ2(N,N')-CH3C6H4SO2NCHPhCHPhNH]; phosphoric acid; triethylamine; In isopropyl alcohol; at 30 ℃; for 3h; Reagent/catalyst; Solvent; Overall yield = 90 %; Overall yield = 28.4 mg; enantioselective reaction; Catalytic behavior; Inert atmosphere; Schlenk technique;
    86 % ee
    With D-Glucose; NADPH; at 30 ℃; for 24h; enantioselective reaction; Enzymatic reaction;
    30 % ee
    Multi-step reaction with 2 steps
    1: borane-ammonia complex
    2: LG-I-D11 / Resolution of racemate; Enzymatic reaction
    With borane-ammonia complex; LG-I-D11;
    With N-Bromosuccinimide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In 1,2-dichloro-ethane; at 0 ℃; for 36h; under 25858.1 Torr; Reagent/catalyst; Solvent; Overall yield = 92 %; Overall yield = 57 mg; enantioselective reaction; Catalytic behavior; Glovebox;
    86 % ee
    With Cp*Ir(biot-p-L)Cl; streptavidin S112A-N118P-K121A mutant; In aq. buffer; at 37 ℃; for 4h; enantioselective reaction; Catalytic behavior; Sealed tube; Enzymatic reaction;
    85 % ee
    With Cp*Ir(biot-p-L)Cl; streptavidin S112A-N118P-K121A mutant; In aq. buffer; at 37 ℃; for 4h; Reagent/catalyst; enantioselective reaction; Catalytic behavior; Sealed tube; Enzymatic reaction;
    86 % ee
    With N-Bromosuccinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,2-dichloro-ethane; at 30 ℃; for 24h; under 25858.1 Torr; enantioselective reaction; Glovebox;
    88 % ee
    With N-Bromosuccinimide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,2-dichloro-ethane; at 0 ℃; for 36h; under 25858.1 Torr; Temperature; Reagent/catalyst; Solvent; Overall yield = 92 %; enantioselective reaction; Glovebox;
    82 % ee
    With Cp*Ir(biot-p-L)Cl; streptavidin S112A-N118P-K121A mutant; sodium formate; In aq. buffer; at 37 ℃; for 48h; pH=6; Reagent/catalyst; Temperature; enantioselective reaction; Catalytic behavior;
    86 % ee
    With Cp*Ir(biot-p-L)Cl; streptavidin S112R-N118P-K121A-S122M-L124Y mutant; sodium formate; In aq. buffer; at 37 ℃; for 48h; pH=6; Reagent/catalyst; Temperature; enantioselective reaction; Catalytic behavior;
    78 % ee
    With sodium formate; sodium hydroxide; In aq. buffer; at 37 ℃; for 48h; pH=7; Reagent/catalyst; Catalytic behavior;
    64 % ee
    With recombinant FPD-chimera streptavidin Sav-FPD; [Cp*Ir(biot-p-L)Cl]; In dimethyl sulfoxide; at 25 ℃; for 16h; pH=7; Reagent/catalyst; enantioselective reaction; Catalytic behavior; Enzymatic reaction;
    60 % ee
    With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C42H46FeP2; hydrogen; trifluoroacetic acid; In tetrahydrofuran; at 30 ℃; for 12h; under 38002.6 Torr; Reagent/catalyst; Temperature; Solvent; enantioselective reaction; Catalytic behavior; Autoclave; Schlenk technique;
    85 % ee
    With Cp*Ir(biot-p-L)Cl; MASMTGGQQMGRDQAGITGTWYNQLGSTFIVTAGADGALTGTYESAVGNAESRYVLTGRYDSAPATDGSGTALGWTVAWKNNYRNAHSATTWSGQYVGGAEARINTQWLLTAGTTEANAWASTLVGHDTFTKVKPSAASIDAAKKAGVNNGNPLDAVQQGSGGGNGGGNGGGNGGGNIDGRGGGNASMTGGQQMGRDQAGITGTWYNQLGSTFIVTAGADGALTGTYVTARGNAESRYVLTGRYDSAPATDGSGTALGWTVAWKNNYRNAHSATTWSGQYVGGAEARINTQWLLTAGTTEANAWASTLVGCDTFTKVKPSAASIDAAKKAGVNNGNPLDAVQQ; In dimethyl sulfoxide; at 25 ℃; for 24h; pH=7; Reagent/catalyst; Sealed tube;
    54 % ee
    With Cp*Ir(biot-p-L)Cl; MASMTGGQQMGRDQAGITGTWYNQLGSTFIVTAGADGALTGTYESAVGNAESRYVLTGRYDSAPATDGSGTALGWTVAWKNNYRNAHSATTWSGQYVGGAEARINTQWLLTAGTTEANAWASTLVGHDTFTKVKPSAASIDAAKKAGVNNGNPLDAVQQGSGGGNGGGNGGGNGGGNIDGRGGGNASMTGGQQMGRDQAGITGTWYNQLGSTFIVTAGADGALTGTYVTARGNAESRYVLTGRYDSAPATDGSGTALGWTVAWKNNYRNAHSATTWSGQYVGGAEARINTQWLLTAGTTEANAWKSTLVGCDTFTKVKPSAASIDAAKKAGVNNGNPLDAVQQ; In dimethyl sulfoxide; at 25 ℃; for 24h; pH=7; Reagent/catalyst; Sealed tube;
    17 % ee
    With 1-dodecyl-3-methylimidazolium bis(2,4,4-trimethylpentyl)phosphinate; C31H33ClN2O8RuS3(2-)*2Na(1+); sodium formate; In n-heptane; water; at 60 ℃; Overall yield = 10 percentChromat.; enantioselective reaction; Inert atmosphere;
    26 % ee
    With formic acid; C33H37ClN2O4RuS; triethylamine; In dichloromethane; at 20 ℃; for 96h; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Schlenk technique;
    49 % ee
    4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
    881834-78-2

    4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

    (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
    22990-19-8,96719-89-0,118864-75-8

    (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

    (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
    180272-45-1

    (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

    Conditions
    Conditions Yield
    4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate; With sodium hydroxide; In ethanol; at 75 - 80 ℃;
    With water; Cooling;

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