3-Quinuclidinyl-4-iodobenzilate

Base Information

• Chemical Name: 3-Quinuclidinyl-4-iodobenzilate
• CAS No.: 81381-93-3
• Molecular Formula: C21H22 I N O3
• Molecular Weight: 463.315
• DSSTox Substance ID: DTXSID601001958
• Nikkaji Number: J357.850J
• ChEMBL ID: CHEMBL275313
• Mol file: 81381-93-3.mol

Synonyms:1-AHIP;1-azabicyclo(2.2.2)oct-3-yl alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate;3-quinuclidinyl-4-(125)iodobenzilate;3-quinuclidinyl-4-iodobenzilate;3-quinuclidinyl-4-iodobenzilate, 123I-labeled;3-quinuclidinyl-4-iodobenzilate, 125I-labeled, (R-(R*,R*))-isomer;3-quinuclidinyl-4-iodobenzilate, I125-labeled;4-IQNB;iodine-123-IQNB

Chemical Property of 3-Quinuclidinyl-4-iodobenzilate

Chemical Property:

• Vapor Pressure: 6.9E-13mmHg at 25°C
• Boiling Point: 549°C at 760 mmHg
• Flash Point: 285.8°C
• PSA: 49.77000
• Density: 1.61g/cm³
• LogP: 3.10240
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 463.06444
• Heavy Atom Count: 26
• Complexity: 494

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=C(C=C4)I)O

Technology Process of 3-Quinuclidinyl-4-iodobenzilate

There total 12 articles about 3-Quinuclidinyl-4-iodobenzilate 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: 57.0%

quinuclidinyl benzilate (6581-06-2) → IQNB (81381-93-3)

Guidance literature:

With iodine; silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1081/SCC-100105877

Reference yield: 54.0%

(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate (81381-92-2) → IQNB (81381-93-3)

Guidance literature:

With methanesulfonic acid; 2,2,2-trifluoroethanol; sodium iodide; for 0.75h; Heating;

DOI:10.1021/jm00368a009

Reference yield:

4-nitrobenzophenone (1144-74-7) → IQNB (81381-93-3)

Guidance literature:

Multi-step reaction with 8 steps

1: ZnI₂ / CH₂Cl₂ / 72 h / Ambient temperature

2: 3 N aq. HCl / 24 h / Ambient temperature

3: 1.) K₂CO₃, dicyclohexano-18-crown-6 / 1.) acetonitrile, RT, 0.5 h, 2.) acetonitrile, RT, 96 h

4: 100 percent / H₂ / Pd-polyethylamine / methanol / 24 h / 2280 Torr

5: 1.) Na / 1.) benzene, reflux, 0.5 h, 2.) benzene, reflux, 24 h

6: 10percent aq. H₂SO₄, sodium nitrite / acetone; H₂O / 0.25 h / 0 °C

7: H₂O / 0.33 h / 0 °C

8: 54 percent / NaI, methanesulfonic acid, trifluoroethanol / 0.75 h / Heating

With hydrogenchloride; perhydrodibenzo-18-crown-6; methanesulfonic acid; 2,2,2-trifluoroethanol; sulfuric acid; hydrogen; sodium; potassium carbonate; sodium iodide; zinc(II) iodide; sodium nitrite; Pd-polyethylamine; In methanol; dichloromethane; water; acetone;

DOI:10.1021/jm00368a009

upstream raw materials:

(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate

quinuclidinyl benzilate

4-nitrobenzophenone

1-(4-aminophenyl)-2-phenylethane-1,2-dione