4-(Rhamnosyloxy)phenylacetonitrile

Base Information

• Chemical Name: 4-(Rhamnosyloxy)phenylacetonitrile
• CAS No.: 122001-32-5
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293
• DSSTox Substance ID: DTXSID60153465
• Nikkaji Number: J615.021G
• Wikidata: Q83020338
• Metabolomics Workbench ID: 134444
• ChEMBL ID: CHEMBL446981
• Mol file: 122001-32-5.mol

Synonyms:4-(rhamnosyloxy)phenylacetonitrile;4-RMOPAN

Chemical Property of 4-(Rhamnosyloxy)phenylacetonitrile

Chemical Property:

• Vapor Pressure: 3.09E-11mmHg at 25°C
• Boiling Point: 510.3°Cat760mmHg
• Flash Point: 262.4°C
• PSA: 102.94000
• Density: 1.368g/cm³
• LogP: -0.04102
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 279.11067264
• Heavy Atom Count: 20
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC=C(C=C2)CC#N)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)CC#N)O)O)O

Technology Process of 4-(Rhamnosyloxy)phenylacetonitrile

There total 3 articles about 4-(Rhamnosyloxy)phenylacetonitrile 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:

4-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyloxy)-phenylacetonitrile → 4-(α-L-rhamnopyranosyloxy)phenylacetonitrile (122001-32-5)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.phymed.2019.153010

Reference yield:

1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose (30021-94-4) → 4-(α-L-rhamnopyranosyloxy)phenylacetonitrile (122001-32-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid hydrazide / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 25 °C

3.1: dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

3.2: 0 - 25 °C / Molecular sieve; Inert atmosphere

4.1: sodium methylate / methanol / 0.5 h / 25 °C / Inert atmosphere

With sodium methylate; acetic acid hydrazide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.phymed.2019.153010

Reference yield:

2,3,4-tri-O-acetyl-α-L-rhamnopyranose (28915-80-2) → 4-(α-L-rhamnopyranosyloxy)phenylacetonitrile (122001-32-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 25 °C

2.1: dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

2.2: 0 - 25 °C / Molecular sieve; Inert atmosphere

3.1: sodium methylate / methanol / 0.5 h / 25 °C / Inert atmosphere

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1016/j.phymed.2019.153010

upstream raw materials:

1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose

2,3,4-tri-O-acetyl-α-L-rhamnopyranose

Refernces