7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene

Base Information

• Chemical Name: 7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene
• CAS No.: 254888-50-1
• Molecular Formula: C18H18NOP
• Molecular Weight: 295.31500
• DSSTox Substance ID: DTXSID90573238
• Nikkaji Number: J1.870.572I
• Mol file: 254888-50-1.mol

Synonyms:254888-50-1;7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene;DTXSID90573238;AKOS024321556;7-azabicyclo[4.1.0]hept-3-en-7-yl(diphenyl)phosphine oxide

Chemical Property of 7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene

Chemical Property:

• PSA: 29.89000
• LogP: 3.25620
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 295.112601195
• Heavy Atom Count: 21
• Complexity: 412

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC2C1N2P(=O)(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of 7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene

There total 3 articles about 7-(Diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene 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: 90.0%

7-azabicyclo[4.1.0]hept-3-ene (6573-99-5) + Diphenylphosphinic chloride (1499-21-4) → 7-(diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene (254888-50-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 50h;

DOI:10.1039/b210608f

Reference yield:

cyclohexa-1,4-diene (1165952-92-0) → 7-(diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene (254888-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: I₂ / tetrahydrofuran / 4 h / -20 °C

1.2: 51 percent / tetrahydrofuran / 1.5 h / Heating

2.1: 88 percent / aq. KOH / 1 h / Heating

3.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 50 h / 20 °C

With dmap; potassium hydroxide; iodine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b210608f

Reference yield:

methyl 6-iodocyclohex-3-en-1-yl carbamate → 7-(diphenylphosphoryl)-7-azabicyclo[4.1.0]hept-3-ene (254888-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / aq. KOH / 1 h / Heating

2: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 50 h / 20 °C

With dmap; potassium hydroxide; triethylamine; In dichloromethane;

DOI:10.1039/b210608f

upstream raw materials:

7-azabicyclo[4.1.0]hept-3-ene

Diphenylphosphinic chloride

cyclohexa-1,4-diene

Downstream raw materials:

(1RS,3SR,5RS,7SR)-8-(diphenylphosphoryl)-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane

(1RS,3RS,5SR,7SR)-8-(diphenylphosphoryl)-4-oxa-8-azatricyclo[5.1.0.0^3,5]octane