7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

Base Information

• Chemical Name: 7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonyl chloride
• CAS No.: 84752-05-6
• Molecular Formula: C₇H₇ClO₂
• Molecular Weight: 158.584
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID10517295
• Mol file: 84752-05-6.mol

Synonyms:84752-05-6;SCHEMBL949713;DTXSID10517295;NWTBDWZQXVGZKY-UHFFFAOYSA-N;7-OXABICYCLO[2.2.1]HEPT-5-ENE-2-CARBONYL CHLORIDE;7-oxa-5-norbornene-2-carbonyl chloride

Chemical Property of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

Chemical Property:

• PSA: 26.30000
• LogP: 1.09530
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 158.0134572
• Heavy Atom Count: 10
• Complexity: 200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC(C1C(=O)Cl)O2

Technology Process of 7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

There total 1 articles about 7-Oxabicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 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: 21.0%

furan (110-00-9) + acryloyl chloride (814-68-6,25189-84-8) → 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride (84752-05-6,58564-81-1,58564-80-0)

Guidance literature:

acryloyl chloride; With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20 ℃;

furan; at 20 ℃;

DOI:10.1055/s-2002-34868

Reference yield:

7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride (84752-05-6,58564-81-1,58564-80-0) → (1S,2S,4R,6R)-2-(1-Methoxy-1-methyl-ethyl)-6-(2-methyl-benzyloxy)-7-oxa-bicyclo[2.2.1]heptane

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine

2: tetrahydrofuran

3: NaH / tetrahydrofuran

4: MCPBA / CH₂Cl₂

5: Superhydride / tetrahydrofuran

6: NaH / tetrahydrofuran

With pyridine; sodium hydride; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: Grignard reaction / 3: Methylation / 4: Epoxidation / 5: Ring cleavage / 6: Alkylation;

DOI:10.1002/ps.2780440116

Reference yield:

7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride (84752-05-6,58564-81-1,58564-80-0) → (1S,2S,4R,6R)-2-(1-Methoxy-1-methyl-propyl)-6-(2-methyl-benzyloxy)-7-oxa-bicyclo[2.2.1]heptane

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine

2: tetrahydrofuran

3: NaH / tetrahydrofuran

4: MCPBA / CH₂Cl₂

5: Superhydride / tetrahydrofuran

6: NaH / tetrahydrofuran

With pyridine; sodium hydride; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: Grignard reaction / 3: Methylation / 4: Epoxidation / 5: Ring cleavage / 6: Alkylation;

DOI:10.1002/ps.2780440116

upstream raw materials:

furan

acryloyl chloride

Downstream raw materials:

(1R,2S,4R)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.0^3,7]nonan-5-one

methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate

rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol