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

• ChemBase ID: 163314
• Molecular Formular: C27H42O4Si
• Molecular Mass: 458.70548
• Monoisotopic Mass: 458.28523636
• 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)O
• 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)O
• InChI: InChI=1S/C27H42O4Si/c1-9-10-11-12-18-15-22-24(23(16-18)31-32(7,8)26(2,3)4)20-17-19(25(28)29)13-14-21(20)27(5,6)30-22/h15-17,20-21H,9-14H2,1-8H3,(H,28,29)/t20-,21-/m1/s1
• InChIKey: VLMKGTYPVASJHP-NHCUHLMSSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 138285-38-8
• PubChem SID: 162257449
• PubChem CID: 10950583

CALCULATED PROPERTIES

• Acid pKa: 4.063283
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.3453465
• LogD (pH = 7.4): 3.6204293
• Log P: 6.7952
• Molar Refractivity: 128.2988 cm^3
• Polarizability: 52.01835 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate

DETAILS

Toronto Research Chemicals - B691110

Used in the preparation of a major Tetrahydrocannabinol (T293200) metabolite.