70434-82-1

Basic information

• Product Name: CP 47497
• Synonyms: CP 47497;rel-3α*-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]cyclohexane-1α*-ol;rel-5-(1,1-Dimethylheptyl)-2-[(1R,3S)-3-hydroxycyclohexyl]phenol;CP 47947;cis-3-(2-Hydroxy-4-(1,1-diMethylheptylphenyl)-cyclohexan-1-;2-[(1R,3S)-3-hydroxycyclohexyl]-5-(2-methyloctan-2-yl)phenol
• CAS NO: 70434-82-1
• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.498
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 70434-82-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 421.2 °C at 760 mmHg
• Flash Point: 180.7 °C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 7.59E-08mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Store at -20°C
• PKA: 10.25±0.40(Predicted)
• CAS DataBase Reference: CP 47497(CAS DataBase Reference)
• NIST Chemistry Reference: CP 47497(70434-82-1)
• EPA Substance Registry System: CP 47497(70434-82-1)

Safety Data

• Hazardous Substances Data: 70434-82-1(Hazardous Substances Data)

Usage

Description

CP 47,497 is a monophenol cannabimimetic compound that binds the central cannabinoid (CB1) receptor with a Ki value of 2.2 nM. It is equivalent in analgesic potency to Δ9-THC and exhibits other CB biological activities as well.

Chemical Properties

White Solid

Uses

A cannabinoid receptor ligand.

Biological Activity

Potent CB 1 receptor agonist (K i = 2.2 nM). Display 3-28-fold > potency than Δ 9 -THC . Exhibits analgesic, motor depressant, anticonvulsant and hypothermic effects in vivo .

InChI:InChI=1/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m1/s1

Synthetic route

(Z)-3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanol (70434-49-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal In ethanol under 760 Torr; for 2h;	77%
With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal

cyclohexenone (930-68-7) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI / tetrahydrofuran / 0.5 h / -3 °C 2: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 3: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene (70120-16-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: Mg / tetrahydrofuran / 20 h / Heating 2: CuI / tetrahydrofuran / 0.5 h / -3 °C 3: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 4: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 3 steps 1: (i) Mg, (ii) CuI, (iii) /BRN= 1280477/ 2: sodium tetrahydroborate 3: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanone (70434-13-8) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 2: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: hydrogen; sodium hydrogencarbonate / palladium on activated charcoal View Scheme

2-(3-hydroxyphenyl)-2-methyloctane (70120-12-6) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 2: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 3: Mg / tetrahydrofuran / 20 h / Heating 4: CuI / tetrahydrofuran / 0.5 h / -3 °C 5: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 6: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-(4-bromo-3-hydroxyphenyl)-2-methyloctane (70120-14-8) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 2: Mg / tetrahydrofuran / 20 h / Heating 3: CuI / tetrahydrofuran / 0.5 h / -3 °C 4: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 5: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-(3-benzyloxyphenyl)-2-methylpropionaldehyde (70120-09-1) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

2-<3-(benzyloxy)phenyl>-2-methylpropionitrile (70120-08-0) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 9 steps 1: 1.) diisobutylaluminium hydride (DIBAL), 2.) aq. H2SO4 / 1.) THF, hexane, 25 deg C, 2 h, 2.) THF, hexane, 25 deg C, 2 h 2: 57 percent / DMSO, NaOH / 4 h / 15 °C 3: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 4: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 5: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 6: Mg / tetrahydrofuran / 20 h / Heating 7: CuI / tetrahydrofuran / 0.5 h / -3 °C 8: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 9: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

1-(benzyloxy)-3-(1,1-dimethyl-2-heptenyl)benzene (70120-10-4) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 7 steps 1: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 2: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 3: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 4: Mg / tetrahydrofuran / 20 h / Heating 5: CuI / tetrahydrofuran / 0.5 h / -3 °C 6: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 7: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

pentyltriphenylphosphonium bromide (21406-61-1) → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 57 percent / DMSO, NaOH / 4 h / 15 °C 2: 78 percent / H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr 3: 100 percent / Br2 / CCl4 / 0.25 h / 30 °C 4: 1.) KH / 1.) DMF, -18 deg C, 15 min, 2.) 25 deg C, 30 min 5: Mg / tetrahydrofuran / 20 h / Heating 6: CuI / tetrahydrofuran / 0.5 h / -3 °C 7: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 8: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

C22H29BrMgO → (Z)-3-<4-(1,1-dimethylheptyl)-2-hydroxyphenyl>cyclohexanol (70434-82-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI / tetrahydrofuran / 0.5 h / -3 °C 2: 51 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / -40 °C 3: 77 percent / H2, NaHCO3 / 10percent Pd/C / ethanol / 2 h / 760 Torr View Scheme

Upstream product

• 21406-61-1 pentyltriphenylphosphonium bromide 
• 70120-10-4 1-(benzyloxy)-3-(1,1-dimethyl-2-heptenyl)benzene 
• 70120-08-0 2-<3-(benzyloxy)phenyl>-2-methylpropionitrile 
• 70120-09-1 2-(3-benzyloxyphenyl)-2-methylpropionaldehyde 
• 70120-14-8 2-(4-bromo-3-hydroxyphenyl)-2-methyloctane 
• 70120-12-6 2-(3-hydroxyphenyl)-2-methyloctane 
• 70434-13-8 3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanone 
• 70120-16-0 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene 
• 930-68-7 cyclohexenone 
• 70434-49-0 (Z)-3-<2-(benzyloxy)-4-(1,1-dimethylheptyl)phenyl>cyclohexanol 

Relevant articles and documents

A Cannabinoid Derived Prototypical Analgesic

The synthesis and analgesic testing of 3-cyclohexanol (1) are described.Prior (SAR) studies led us to conclude that the pyran ring of 9-nor-9β-hydroxyhexahydrocannabinol (HHC) was not necessary for the expression of biological activity in this series of cannabinoids.Analysis of models and the use of molecular mechanics calculations suggested that a simpler compound, such as 1, would possess the biological activity of HHC.Compound 1 was prepared in nine steps from acetonitrile (2).Biological testing in five models of pain shows that compound 1 and morphine are equally potent as analgesics and demonstrates that the pyran ring of HHC is not necessary for biological activity.Further simplification of 1 was pursued by the synthesis of 4--2-pentanol (17), but this derivative exhibits significantly reduced analgesic activity.