Tropoxane

Base Information

• Chemical Name: Tropoxane
• CAS No.: 192461-10-2
• Molecular Formula: C₁₅H₁₆Cl₂O₃
• Molecular Weight: 315.196
• DSSTox Substance ID: DTXSID801028338
• Nikkaji Number: J873.203E
• Wikipedia: Tropoxane
• Wikidata: Q7846271
• Mol file: 192461-10-2.mol

Synonyms:Tropoxane;Tropoxane (O-1072);SCHEMBL20942841;DTXSID801028338;Q7846271;(1R,2S,5S)-3beta-(3,4-Dichlorophenyl)-8-oxabicyclo[3.2.1]octane-2beta-carboxylic acid methyl ester;192461-10-2

Chemical Property of Tropoxane

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 314.0476498
• Heavy Atom Count: 20
• Complexity: 376

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2CCC(O2)CC1C3=CC(=C(C=C3)Cl)Cl
• Isomeric SMILES: COC(=O)[C@@H]1[C@H]2CC[C@H](O2)C[C@@H]1C3=CC(=C(C=C3)Cl)Cl

Technology Process of Tropoxane

There total 3 articles about Tropoxane 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: 45.0%

O-1059 (192461-09-9) → O-1072 (192461-10-2) + O-1066 (192461-11-3)

Guidance literature:

With methanol; samarium diiodide; In tetrahydrofuran; at -70 ℃; for 2h;

DOI:10.1021/jm9703045

Reference yield:

3,4-dichlophenylboronic acid (151169-75-4) → O-1072 (192461-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / LiCl, tris(dibenzylideneacetone)dipalladium, Na₂CO₃ / various solvent(s) / 1 h / Heating

2: 13 percent / SmI₂, methanol / tetrahydrofuran / 2 h / -70 °C

With methanol; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; samarium diiodide; sodium carbonate; lithium chloride; In tetrahydrofuran;

DOI:10.1021/jm9703045

Reference yield:

(1R,5S)-3-Trifluoromethanesulfonyloxy-8-oxa-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester → O-1072 (192461-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / LiCl, tris(dibenzylideneacetone)dipalladium, Na₂CO₃ / various solvent(s) / 1 h / Heating

2: 13 percent / SmI₂, methanol / tetrahydrofuran / 2 h / -70 °C

With methanol; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; samarium diiodide; sodium carbonate; lithium chloride; In tetrahydrofuran;

DOI:10.1021/jm9703045

upstream raw materials:

O-1059

3,4-dichlophenylboronic acid

Downstream raw materials:

(1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-hydroxymethyl-8-oxabicyclo[3.2.1]octane

Refernces

• 1、 Meltzer, Peter C.,Liang, Anna Y.,Blundell, Paul,Gonzalez, Mario D.,Chen, Zhengming,George, Clifford,Madras, Bertha K.. "2-carbomethoxy-3-aryl-8-oxabicyclo[3.2.1]octanes: Potent non-nitrogen inhibitors of monoamine transporters". . p. 2661 - 2673. Retrieved 2007/10/03.