(S)-(+)-1,2,3,4-Tetrahydro-1-naphthol

Base Information

• Chemical Name: (S)-(+)-1,2,3,4-Tetrahydro-1-naphthol
• CAS No.: 53732-47-1
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• European Community (EC) Number: 623-721-8
• UNII: 50MT77537D
• Nikkaji Number: J330.337C
• Wikidata: Q27260807
• ChEMBL ID: CHEMBL206199
• Mol file: 53732-47-1.mol

Synonyms:53732-47-1;(S)-(+)-1,2,3,4-Tetrahydro-1-naphthol;(S)-1,2,3,4-tetrahydronaphthalen-1-ol;(s)-1-tetralol;1-Tetralol, (S)-;(1S)-1,2,3,4-tetrahydronaphthalen-1-ol;(S)-Tetralin-1-ol;(S)-1-Hydroxytetralin;S-Tetralol;(S)-(+)-alpha-Tetralol;(S)-1,2,3,4-tetrahydro-1-naphthol;(S)-1-Tetralinol;(+)-1-Tetralol;(S)-(+)-1-Tetralol;J330.337C;CHEMBL206199;(+)-1,2,3,4-Tetrahydro-1-naphthol;50MT77537D;1-Naphthalenol, 1,2,3,4-tetrahydro-, (1S)-;1-Naphthalenol, 1,2,3,4-tetrahydro-, (S)-(+)-;MFCD00063006;S)-(+)-1,2,3,4-Tetrahydro-1-naphthol;1,2,3,4-Tetrahydro-naphthalen-1-ol;(s)-alpha-tetralol;(+)-alpha-Tetralol;SCHEMBL3583014;SGCUT00116;(+)-.ALPHA.-TETRALOL;UNII-50MT77537D;BDBM26271;JAAJQSRLGAYGKZ-JTQLQIEISA-N;to_000012;AKOS015833090;AS-81167;TS-01947;S-(+)-1,2,3,4-tetrahydro-1-naphthol;(1S)-1,2,3,4-tetrahydro-1-naphthalenol;CS-0079961;T2360;(S)-1-hydroxy-1,2,3,4-tetrahydronaphthalene;EN300-216467;T72587;A829313;A870642;(S)-(+)-1,2,3,4-Tetrahydro-1-naphthol, 99%;Q27260807;(S)-(+)-1,2,3,4-Tetrahydro-1-naphthol, puriss., >=99.0% (sum of enantiomers, GC)

Chemical Property of (S)-(+)-1,2,3,4-Tetrahydro-1-naphthol

Chemical Property:

• Melting Point: 37-39 °C
• Refractive Index: 33 ° (C=2.5, CHCl3)
• Boiling Point: 254.8 °C at 760 mmHg
• PKA: 14.33±0.20(Predicted)
• Flash Point: 99.9 °C
• PSA: 20.23000
• Density: 1.112g/cm³
• LogP: 2.05630
• Solubility.: almost transparency in Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)?-?(+)?-?1,?2,?3,?4-?Tetrahydro-?1-?naphthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2=CC=CC=C2C1)O
• Isomeric SMILES: C1C[C@@H](C2=CC=CC=C2C1)O
• Uses: (S)?-?(+)?-?1,?2,?3,?4-?Tetrahydro-?1-?naphthol is a building block used in pharmaceutical chemistry such as in the synthesis of a potent and orally bioavailable GPR40 agonist acting as a novel insulin secretagogues with low risk of hypoglycemia

Technology Process of (S)-(+)-1,2,3,4-Tetrahydro-1-naphthol

There total 53 articles about (S)-(+)-1,2,3,4-Tetrahydro-1-naphthol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

3,4-dihydronaphthalene-1(2H)-one (529-34-0) → (R)-(-)-1,2,3,4-tetrahydro-1-naphthol (529-33-9,23357-45-1,53732-47-1,87248-51-9)

Guidance literature:

With 2-(ethylamino)pyridine; lithium aluminium tetrahydride; (-)-N-methylephedrine; In diethyl ether; at -78 ℃; for 3h;

Reference yield: 68.0%

1,2,3,4-Tetrahydro-1-naphthol (529-33-9) → (S)-1-tetralol (53732-47-1) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0)

Guidance literature:

With 3 A molecular sieve; oxygen; (-)-sparteine; palladium dichloro (η-2,5-norbornadiene); In toluene; at 80 ℃; for 40h; under 760.051 Torr;

DOI:10.1021/ja015791z

Reference yield: 44.0%

1,2,3,4-Tetrahydro-1-naphthol (529-33-9) + chlorotris(p-methylphenyl)silane (18740-66-4) → (S)-1-tetralol (53732-47-1) + ((1,2,3,4-tetrahydronaphthalen-1-yl)oxy)tri-p-tolylsilane + (R)-1-tetralol (23357-45-1)

Guidance literature:

1,2,3,4-Tetrahydro-1-naphthol; With Levamisole; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 ℃; Inert atmosphere; Molecular sieve; Resolution of racemate;

chlorotris(p-methylphenyl)silane; In tetrahydrofuran; at -78 ℃; for 48h; enantioselective reaction; Inert atmosphere; Molecular sieve; Resolution of racemate;

DOI:10.1021/jo402569h

upstream raw materials:

1,2,3,4-Tetrahydro-1-naphthol

tetralin

3,4-dihydronaphthalene-1(2H)-one

(S)-1,2,3,4-tetrahydro-1-naphthylbutyrate

Refernces

• 1、 Li, Aipeng,Ting, Wang,Yang, Ke,Zhang, Xuanshuo,Yin, Dongming,Qin, Yong,Zhang, Lianbing. "Engineering a Carbonyl Reductase as a Potential Tool for the Synthesis of Chiral α-Tetralinols". . p. 4625 - 4633. Retrieved 2021.
• 2、 Karasawa, Masayuki,Shoji, Osami,Stanfield, Joshua Kyle,Suzuki, Kazuto,Yonemura, Kai. "Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3-Based Whole-Cell Biocatalyst". supporting information. . Retrieved 2021/12/16.
• 3、 Oestreich, Martin,Seliger, Jan. "Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts". . p. 247 - 251. Retrieved 2020/10/29.