(S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Chemical Properties

Melting point:

54-56°C

Boiling point:

54-56°C

Density 

1.186±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform

form 

Solid

pka

4.28±0.20(Predicted)

color 

White

InChI

InChI=1S/C11H12O2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7H2,(H,12,13)/t10-/m0/s1

InChIKey

VDLWTJCSPSUGOA-JTQLQIEISA-N

SMILES

[C@@H]1(C(O)=O)C2=C(C=CC=C2)CCC1

CAS DataBase Reference

85977-52-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-51

Safety Statements 

26-24/25

HS Code 

29163990

(S)-(-)-1,2,3,4-Tetrahedro-naphthoic acid Usage And Synthesis

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Dipeptidyl Boronate Proteasome Inhibitors.

Synthesis

General procedure for the synthesis of (S)-tetrahydronaphthalenecarboxylic acid from 1,2,3,4-tetrahydro-1-naphthalenecarboxylic acid: 15.6 g (0.1 mol) of 1,2,3,4-tetrahydronaphthalenecarboxylic acid and 29.8 g (0.1 mol) of quinine were added to 158 mL of a 50% (v/v) aqueous ethanol solution, and stirred for 30 min at 50 °C until complete dissolution. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent ratio of petroleum ether (PE):ethyl acetate (EA) = 1:2. Upon completion of the reaction, the reaction solution was cooled to below 0 °C overnight to promote crystallization. Subsequent to filtration, the solid was collected and dried. The dried solid was recrystallized with 90 mL of ethanol, crystallized again at 0 °C, diafiltrated and dried. The resulting product was dissolved in a mixture of 55 mL of 1 mol/L hydrochloric acid and 100 mL of ethyl acetate in a partitioning operation. The organic phase was dried and filtered and concentrated to obtain the crude product. Finally, the crude product was recrystallized from hexane to give 7.21 g of (S)-1,2,3,4-tetrahydronaphthalenecarboxylic acid in the form of white solid in 43.6% yield.

References

[1] Patent: CN108084176, 2018, A. Location in patent: Paragraph 0093; 0102; 0103; 0104
[2] Arkiv foer Kemi, 1958, vol. 12, p. 161,165
[3] Patent: CN107382697, 2017, A

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