Dihydroisocodeine

Base Information

• Chemical Name: Dihydroisocodeine
• CAS No.: 795-38-0
• Molecular Formula: C18H23NO3
• Molecular Weight: 301.386
• UNII: 9H2016E13H
• DSSTox Substance ID: DTXSID2048907
• Nikkaji Number: J72.594C
• Wikipedia: Dihydroisocodeine
• Wikidata: Q15634044
• ChEMBL ID: CHEMBL3187185
• Mol file: 795-38-0.mol

Synonyms:Contugesic;DF 118;DHC Continus;DHC Mundipharma;Dicodin;dihydrocodeine;dihydrocodeine acetate, (5alpha,6alpha)-isomer;dihydrocodeine bitartrate;dihydrocodeine hydrochloride, (5alpha,6alpha)-isomer;dihydrocodeine phosphate (1:1), (5alpha,6alpha)-isomer;dihydrocodeine tartrate (1:1), (5alpha,6alpha)-(R-(R*,R*))-isomer;dihydrocodeine tartrate (1:1), (5alpha,6beta)-(R-(R*,R*))-isomer;dihydrocodeine, (5alpha,6alpha,14alpha)-isomer;dihydrocodeine, (5alpha,6beta)-isomer;dihydrocodeine, (5alpha,6beta,14alpha)-isomer;dihydrocodeine, thiocyanate salt (5alpha,6alpha)-isomer;Paracodin;Paracodina;paramol 118;Rikodeine;Tiamon;Tosidrin

Chemical Property of Dihydroisocodeine

Chemical Property:

• Vapor Pressure: 2.48E-09mmHg at 25°C
• Melting Point: 199-200°
• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• PSA: 41.93000
• Density: 1.31g/cm³
• LogP: 1.66300
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 301.16779360
• Heavy Atom Count: 22
• Complexity: 471

Purity/Quality:

99% ^*data from raw suppliers

6β-Hydrocodol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@@H](CC4)O

Technology Process of Dihydroisocodeine

There total 54 articles about Dihydroisocodeine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

(+/-)-dihydrocodeinone (74035-75-9) → (+/-)-dihydrocodeine (125-28-0,795-38-0,28379-49-9,29699-74-9,144408-29-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

DOI:10.1039/c7sc03189k

Reference yield: 70.0%

N-[2-(3-hydroxy-5-methoxy-1,3,3a,9a-tetrahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide → (+/-)-dihydrocodeine (125-28-0,795-38-0,28379-49-9,29699-74-9,144408-29-7)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; tert-butyl alcohol; at -78 ℃; for 0.166667h;

DOI:10.1021/jo0513008

Reference yield:

Hydrocodone (125-29-1) → dihydro-isocodeine (795-38-0) + 4,5α-epoxy-3,6β-dimethoxy-17-methyl-morphinane (41714-53-8)

Guidance literature:

With methanol; sodium tetrahydroborate;

DOI:10.1021/ja01596a036

upstream raw materials:

Hydrocodone

2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol

6-bromoguaiacol

2-(5-methoxy-cyclohexa-1,4-dienyl)-ethylamine

Downstream raw materials:

Hydrocodone

Refernces

Formal synthesis of (-)-morphine from d-glucal based on the cascade Claisen rearrangement

10.1016/j.tetlet.2007.11.037

The research centers on the formal synthesis of (-)-morphine, commencing from D-glucal. The core experimental procedures involve the preparation of the C-ring using Ferrier's carbocyclization reaction and the stereoselective generation of adjacent tertiary and quaternary carbons in the C-ring through a cascade Claisen rearrangement. The synthesis sequence includes a Suzuki-Miyaura coupling to form an intermediate, followed by the crucial cascade Claisen rearrangement to construct the adjacent tertiary and quaternary carbons, which are integral to the morphine structure. Subsequently, an intramolecular Friedel-Crafts type reaction is employed to build the ABCE-phenanthrofuran skeleton, and the introduction of a tosylamide function precedes a reductive cyclization to yield (-)-dihydroisocodeine, a known synthetic intermediate for (-)-morphine. Various analytical techniques, such as nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, mass spectrometry (MS), and elemental analysis, are utilized to characterize the newly synthesized compounds. The reactants encompass a range of organic acids, alkali metals, organic boronic acids, and D-glucal derivatives.