(1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one

Base Information

• Chemical Name: (1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one
• CAS No.: 652991-03-2
• Molecular Formula: C22H22O3
• Molecular Weight: 334.415
• DSSTox Substance ID: DTXSID40450247
• Wikidata: Q82269871
• Mol file: 652991-03-2.mol

Synonyms:652991-03-2;CTK1J7599;DTXSID40450247;(1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one

Chemical Property of (1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 334.15689456
• Heavy Atom Count: 25
• Complexity: 474

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C=CC(C1=O)C(C2OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@@H]2C=C[C@H](C1=O)[C@H]([C@@H]2OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of (1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one

There total 2 articles about (1S,4R,7R,8R)-7,8-bis(phenylmethoxy)bicyclo[2.2.2]oct-5-en-2-one 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: 83.0%

(1S,2R,4R,7R,8R)-7,8-Bis-benzyloxy-2-chloro-bicyclo[2.2.2]oct-5-ene-2-carbonitrile (652990-95-9) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one (652991-03-2)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 48h;

DOI:10.1039/b301271a

Reference yield:

(-)-(5R,6R)-5,6-bis(benzyloxy)cyclohexa-1,3-diene (514854-09-2) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one (652991-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 2,6-lutidine / 12 h / 95 °C

2: 83 percent / aq. KOH / dimethylsulfoxide / 48 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; In dimethyl sulfoxide; 1: Diels-Alder reaction;

DOI:10.1039/b301271a

Reference yield: 94.0%

toluene-4-sulfonic acid hydrazide (1576-35-8) + (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one (652991-03-2) → (1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone (652991-05-4)

Guidance literature:

In methanol; at 20 ℃; for 24h;

DOI:10.1039/b301271a

upstream raw materials:

(1S,2R,4R,7R,8R)-7,8-Bis-benzyloxy-2-chloro-bicyclo[2.2.2]oct-5-ene-2-carbonitrile

(-)-(5R,6R)-5,6-bis(benzyloxy)cyclohexa-1,3-diene

Downstream raw materials:

(1S,4R,7R,8R)-7,8-bis(benzyloxy)bicyclo[2.2.2]oct-5-en-2-one p-tosylhydrazone