(-)-2-Cyano-6-phenyloxazolopiperidine

Base Information

• Chemical Name: (-)-2-Cyano-6-phenyloxazolopiperidine
• CAS No.: 88056-92-2
• Molecular Formula: C14H16 N2 O
• Molecular Weight: 228.294
• Hs Code.: 2934999090
• European Community (EC) Number: 635-825-0
• Nikkaji Number: J602.452A
• Wikidata: Q76145948
• Mol file: 88056-92-2.mol

Synonyms:88056-92-2;(-)-2-Cyano-6-phenyloxazolopiperidine;(3R,5S,8AR)-3-phenylhexahydro-2H-oxazolo[3,2-a]pyridine-5-carbonitrile;(3R,5S,8aR)-3-phenyl-3,5,6,7,8,8a-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile;(3R,5S,8aR)-3-Phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile;(2S,6R,9R)-9-phenyl-7-oxa-1-azabicyclo[4.3.0]nonane-2-carbonitrile;(3R,5S,8aR)-(-)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile;SCHEMBL2882752;AKOS005256850;AS-72663;C1363;T71426;(-)-5-Cyano-3-phenyl-2,3,5,6,7,8-hexahydro-5H-oxazolo[3,2-a]pyridine;(-)-2,3,5,6,7,8-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile;(3R,5S,8aR)-(-)-Hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile, 97%;(3R,5S,8AR)-3-PHENYL-HEXAHYDRO-2H-[1,3]OXAZOLO[3,2-A]PYRIDINE-5-CARBONITRILE;(8aalpha)-3beta-Phenylhexahydro-5H-oxazolo[3,2-a]pyridine-5alpha-carbonitrile

Chemical Property of (-)-2-Cyano-6-phenyloxazolopiperidine

Chemical Property:

• Vapor Pressure: 2.23E-06mmHg at 25°C
• Melting Point: 82 °C
• Refractive Index: -285 ° (C=1, CHCl3)
• Boiling Point: 392.8°C at 760 mmHg
• Flash Point: 191.4°C
• PSA: 36.26000
• Density: 1.18
• LogP: 2.39998
• Solubility.: soluble in Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.126263138
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-2-Cyano-6-phenyloxazolopiperidine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N2C(C1)OCC2C3=CC=CC=C3)C#N
• Isomeric SMILES: C1C[C@H](N2[C@@H](C1)OC[C@H]2C3=CC=CC=C3)C#N

Technology Process of (-)-2-Cyano-6-phenyloxazolopiperidine

There total 5 articles about (-)-2-Cyano-6-phenyloxazolopiperidine 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: 70.0%

potassium cyanide + D-2-phenylglycinol (56613-80-0) + Glutaraldehyde (111-30-8,29257-65-6,79215-57-9) → (-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2)

Guidance literature:

D-2-phenylglycinol; Glutaraldehyde; With citric acid; In water; at 0 ℃; pH=4;

potassium cyanide; In dichloromethane; water; at 20 ℃; for 3h;

With zinc dibromide; for 3h; Inert atmosphere;

DOI:10.15227/orgsyn.070.0054

Reference yield: 63.0%

(R)-2-Amino-1-phenylethanol (2549-14-6,1936-63-6) + potassium cyanide (151-50-8) + Glutaraldehyde (111-30-8,29257-65-6,79215-57-9) → (-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2)

Guidance literature:

(R)-2-Amino-1-phenylethanol; Glutaraldehyde; With citric acid; In water; at 0 ℃; for 0.5h;

potassium cyanide; In dichloromethane; water; at 0 - 20 ℃; for 3.5h;

With sodium hydroxide; zinc dibromide; more than 3 stages;

Reference yield:

D-2-phenylglycinol (56613-80-0) → (-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O / 1 h / pH 3.0

2: H₂O / 72 h / Ambient temperature; pH 3.0

In water;

DOI:10.1021/ja00364a053

upstream raw materials:

potassium cyanide

D-2-phenylglycinol

Glutaraldehyde

(R)-2-Amino-1-phenylethanol

Downstream raw materials:

(3R,5R,8aR)-5-(2-[1,3]Dioxolan-2-yl-ethyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(3R,8aR)-5-(2-[1,3]Dioxolan-2-yl-ethyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(3R,5R,8aR)-5-Benzo[1,3]dioxol-5-ylmethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

(2R)-2-((1S,5S)-7-butyl-6,8-diazabicyclo[3.2.1]oct-6-en-8-yl)-2-phenylethanol

Refernces

• 1、 Royer, Jacques,Husson, Henri-Phillipe. "A NEW POTENTIAL ACYL IMINIUM ION FOR THE ASYMMETIRIC SYNTHESIS OF PIPERIDINE DERIVATIVES". . p. 1493 - 1496. Retrieved 2007/10/02.
• 2、 Royer, Jacques,Husson, Henri-Philippe. "Asymmetric Synthesis. 2. Practical Method for the Asymmetric Synthesis of Indolizidine Alkaloids: Total Synthesis of (-)-Monomorine I". . p. 670 - 673. Retrieved 2007/10/02.