N-(Cyclopropylmethyl)normorphine

Base Information

• Chemical Name: N-(Cyclopropylmethyl)normorphine
• CAS No.: 1976-45-0
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.408
• DSSTox Substance ID: DTXSID20173442
• Nikkaji Number: J406.898J
• Wikidata: Q83043503
• Mol file: 1976-45-0.mol

Synonyms:N-(cyclopropylmethyl)normorphine

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Chemical Property of N-(Cyclopropylmethyl)normorphine

Chemical Property:

• Vapor Pressure: 1.33E-11mmHg at 25°C
• Boiling Point: 519.1°Cat760mmHg
• Flash Point: 267.8°C
• PSA: 52.93000
• Density: 1.42g/cm³
• LogP: 1.91620
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 325.16779360
• Heavy Atom Count: 24
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C2CC6=C3C(=C(C=C6)O)OC4C(C=C5)O
• Isomeric SMILES: C1CC1CN2CC[C@]34[C@@H]5[C@H]2CC6=C3C(=C(C=C6)O)O[C@H]4[C@H](C=C5)O

Technology Process of N-(Cyclopropylmethyl)normorphine

There total 14 articles about N-(Cyclopropylmethyl)normorphine 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%

3-O,N-dicyclopropylcarbonylnormorphine (81815-58-9) → 17-(cyclopropylmethyl)normorphine (1976-45-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 23h; Ambient temperature;

DOI:10.1248/cpb.39.2000

Reference yield:

cyclopropylcarbinyl bromide (7051-34-5) + 3-<(vinyloxy)carbonyl>normorphine hydrobromide (91265-72-4) → 17-(cyclopropylmethyl)normorphine (1976-45-0)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 80 ℃; for 10h;

DOI:10.1021/jm00376a026

Reference yield:

normorphine (466-97-7,13396-02-6,99295-16-6,142864-36-6) → 17-(cyclopropylmethyl)normorphine (1976-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / triethylamine / CHCl₃ / 8 h / Heating

2: 74 percent / LiAlH₄ / tetrahydrofuran / 23 h / Ambient temperature

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; chloroform;

DOI:10.1248/cpb.39.2000

upstream raw materials:

cyclopropanecarboxylic acid chloride

17-cyclopropanecarbonyl-3,6α-bis-cyclopropanecarbonyloxy-4,5α-epoxy-morphin-7-ene

17-(cyclopropylmethyl)-7,8-didehydro-4,5α-epoxy-3-methoxymorphinan-6α-ol

3-O,N-dicyclopropylcarbonylnormorphine

Downstream raw materials:

(-)-3-Acetyl-6β-(acetylthio)-N-(cyclopropylmethyl)normorphine

17-(cyclopropylmethyl)normorphinone