ethyl (6aR,10aR)-1-[(tert-butyldimethylsilyl)oxy]-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate

• ChemBase ID: 163315
• Molecular Formular: C29H46O4Si
• Molecular Mass: 486.75864
• Monoisotopic Mass: 486.31653648
• SMILES: C1(=C[C@@H]2[C@@H](CC1)C(Oc1c2c(cc(c1)CCCCC)O[Si](C(C)(C)C)(C)C)(C)C)C(=O)OCC
• Canonical SMILES: CCCCCc1cc2OC(C)(C)[C@H]3[C@H](c2c(c1)O[Si](C(C)(C)C)(C)C)C=C(CC3)C(=O)OCC
• InChI: InChI=1S/C29H46O4Si/c1-10-12-13-14-20-17-24-26(25(18-20)33-34(8,9)28(3,4)5)22-19-21(27(30)31-11-2)15-16-23(22)29(6,7)32-24/h17-19,22-23H,10-16H2,1-9H3/t22-,23-/m1/s1
• InChIKey: HFGATAWDKZPRPB-DHIUTWEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (6aR,10aR)-1-[(tert-butyldimethylsilyl)oxy]-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate
• IUPAC Traditional name: ethyl (6aR,10aR)-1-[(tert-butyldimethylsilyl)oxy]-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate
• Synonyms: (6aR,10aR)-1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-6a,7,8,10a-tetrahydro-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid Ethyl Ester; 1-O-[(tert-Butyl)dimethylsilyloxy]-9-carboxylic Acid Ethyl Ester Δ9-Tetrahydro Cannabinol

Database IDs

• CAS Number: 1262438-66-3
• PubChem SID: 162257450
• PubChem CID: 71314381

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 7.8694
• LogD (pH = 7.4): 7.8694
• Log P: 7.8694
• Molar Refractivity: 137.8165 cm^3
• Polarizability: 55.960075 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B691113

Used in the preparation of Tetrahydrocannabinol (T293200) derivatives. Used in the assessment of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid ethyl ester as a metabolite formed during the combined consumption of cannabis and alcohol.

REFERENCES

• Nadulski, T. et al.; Forensic Sci. Int. 196, 78 (2010)