13965-63-4

Basic information

• Product Name: (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol
• CAS NO: 13965-63-4
• Molecular Formula: C₃₁H₃₇NO₄
• Molecular Weight: 487.6298
• Mol File: 13965-63-4.mol
• Article Data: 2

Chemical Properties

• Density: 1.27g/cm³
• Refractive Index: 1.652
• CAS DataBase Reference: (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol(13965-63-4)
• EPA Substance Registry System: (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol(13965-63-4)

Safety Data

• Hazardous Substances Data: 13965-63-4(Hazardous Substances Data)

Usage

General Description

The chemical "(2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol" is a complex compound with a morphinan structure. It contains a 4-phenylbutan-2-ol group attached to the 18th carbon of the morphinan ring, which is a common component of opioid drugs. The compound also features multiple methoxy groups and a double bond within the morphinan ring, making it a highly complex and potentially potent molecule. Its stereochemistry is specified as (2R)-2, indicating the configuration of its chiral centers. (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol likely has significant pharmacological activity, potentially as an opioid or related analgesic drug.

Synthetic route

thevinone (15358-22-2) + 2-phenyl-ethylmagnesium halide → (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4)

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (20R)-phenethyl-orvinol (14521-98-3)

Conditions	Yield
With potassium hydroxide In diethylene glycol Heating;

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphin-15-en-7α-yl)-4-phenyl-butan-2-ol (36418-76-5)

Conditions	Yield
With hydrogen sulfide; mercury(II) oxide In acetic acid

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (2R,2'R)-4,4'-diphenyl-2,2'-[4,5α;4',5'α-diepoxy-3,6,3',6'-tetramethoxy-17,17'-methanediyl-bis-(6α,14α-etheno-morphinan-7α-yl)]-bis-butan-2-ol (16620-48-7, 16659-03-3)

Conditions	Yield
(i) diazenedicarbocylic acid diethyl ester, acetone, (ii) aq. H2O; Multistep reaction;

Upstream product

• 15358-22-2 thevinone 
• 3277-89-2 phenethylmagnesium bromide 

Downstream Products

• 14521-98-3 (20R)-phenethyl-orvinol 
• 36418-76-5 (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphin-15-en-7α-yl)-4-phenyl-butan-2-ol 
• 16620-48-7 (2R,2'R)-4,4'-diphenyl-2,2'-[4,5α;4',5'α-diepoxy-3,6,3',6'-tetramethoxy-17,17'-methanediyl-bis-(6α,14α-etheno-morphinan-7α-yl)]-bis-butan-2-ol 
• 14521-98-3 (20R)-(5α,7α)-4,5-epoxy-3-hydroxy-6-methoxy-α,17-dimethyl-α-(2-phenylethyl)-6,14-ethenomorphinan-7-methanol 

Relevant articles and documents

Synthesis and evaluation of a full-agonist orvinol for PET-imaging of opioid receptors: [11C]PEO

Antagonist radiotracers have shown only a low sensitivity for detecting competition from high-efficacy agonists at opioid receptors (ORs) in vivo. We report that [11C]PEO binds with high affinity to μ and κ-opioid receptors, is a full agonist, and concentrates in brain regions of rats with a high density of the μ-OR after intravenous injection. Blocking studies with μ and κ-OR selective compounds demonstrated that the binding of [11C]PEO is saturable and selective to the μ-OR in rat brain.