6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Base Information

• Chemical Name: 6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one
• CAS No.: 26097-15-4
• Molecular Formula: C₉H₁₁IO₂
• Molecular Weight: 278.09
• NSC Number: 167916
• DSSTox Substance ID: DTXSID00304873
• Mol file: 26097-15-4.mol

Synonyms:26097-15-4;NSC167916;DTXSID00304873;NSC-167916;6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Chemical Property of 6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Chemical Property:

• Vapor Pressure: 1.31E-05mmHg at 25°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 277.98038
• Heavy Atom Count: 12
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2CC3C1C(=O)OC3C2I

Technology Process of 6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

There total 1 articles about 6-iodo-7-methylhexahydro-2H-3,5-methanocyclopenta[b]furan-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:

(E)-but-2-enoic acid (107-93-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (3-endo,2-exo)-3-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (4397-23-3,4397-24-4,16651-50-6,31329-97-2,53624-84-3,65942-11-2,127179-45-7,130793-97-4,139891-78-4) + 6-endo-hydroxy-5-exo-iodo-3-exo-methylnorborn-2-endo-ylcarboxylic acid γ-lactone (26097-15-4,103000-85-7,131432-93-4)

Guidance literature:

(E)-but-2-enoic acid; cyclopenta-1,3-diene; With lithium perchlorate; ethylene glycol; In water;

With iodine; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1021/ol060741q

Reference yield: 71.0%

silver(I) 4-methylbenzenesulfonate (16836-95-6) + 6-endo-hydroxy-5-exo-iodo-3-exo-methylnorborn-2-endo-ylcarboxylic acid γ-lactone (26097-15-4,103000-85-7,131432-93-4) → C9H11O2(1+) + 7-syn-hydroxy-5-endo-methyl-3-exo-p-tolylsulphonyloxynorborn-6-exo-ylcarboxylic acid γ-lactone (86960-85-2) + 6-endo-hydroxy-3-exo-methyl-5-exo-p-tolylsulphonyloxynorborn-2-endo-ylcarboxylic acid γ-lactone (86960-84-1)

Guidance literature:

In acetonitrile; for 40h; Product distribution; Heating;

Reference yield:

6-endo-hydroxy-5-exo-iodo-3-exo-methylnorborn-2-endo-ylcarboxylic acid γ-lactone (26097-15-4,103000-85-7,131432-93-4) → endo-2-carbomethoxy-exo-3-methylbicyclo[2,2,1]hept-5-ene (7167-30-8,7288-31-5,16651-51-7,17660-75-2,23217-30-3,89577-04-8,136375-14-9,155325-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn; glacial acetic acid / 3 h

2: H₂SO₄ / 18 h / Heating

With sulfuric acid; acetic acid; zinc;

DOI:10.1021/ol060741q

upstream raw materials:

(E)-but-2-enoic acid

cyclopenta-1,3-diene

Downstream raw materials:

endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid

7-syn-hydroxy-5-endo-methyl-3-exo-p-tolylsulphonyloxynorborn-6-exo-ylcarboxylic acid γ-lactone

6-endo-hydroxy-3-exo-methyl-5-exo-p-tolylsulphonyloxynorborn-2-endo-ylcarboxylic acid γ-lactone

6-endo-hydroxy-3-exo-methylnorborn-2-endo-ylcarboxylic acid γ-lactone