2H-pyran

Base Information

• Chemical Name: 2H-pyran
• CAS No.: 289-66-7
• Molecular Formula: C5H6O
• Molecular Weight: 82.102
• UNII: CH5P2A5WTT
• Nikkaji Number: J247.837D
• Wikipedia: Pyran
• Wikidata: Q217356
• Metabolomics Workbench ID: 55150
• Mol file: 289-66-7.mol

Synonyms:Pyran;Pyrans

Chemical Property of 2H-pyran

Chemical Property:

• PSA: 9.23000
• LogP: 1.08650
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 82.041864811
• Heavy Atom Count: 6
• Complexity: 81.9

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC=CO1

Technology Process of 2H-pyran

There total 4 articles about 2H-pyran 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: 65.0%

→ (+/-)-1'-benzoyl-3,4-dihydro-6-methanesulfonamido-4-(1-pyrrolidinyl)-spiro[2H-1-benzopyran-2,4'-piperidine] + 1,2-dihydropyrane (289-66-7)

Guidance literature:

Reference yield: 49.0%

→ 2-methoxy-4-methyl-5,6-dihydro-6 [2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)-buta-1,3-dienyl]-2H-pyran (62824-30-0) + 1,2-dihydropyrane (289-66-7)

Guidance literature:

Reference yield:

β-acetoxy-crotonic acid methyl ester (4525-27-3) + 4-chlorobenzaldehyde (104-88-1) → 1,2-dihydropyrane (289-66-7) + dimethyl 4-(4-chlorophenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate

Guidance literature:

Zinc chloride;

upstream raw materials:

β-acetoxy-crotonic acid methyl ester

4-chlorobenzaldehyde

Downstream raw materials:

3,4-dihydrobenzo[cd]indol-5(1H)-one

3,4,5,6-Tetrahydro-2-hydroxy-3-phenylseleno-2H-pyran

1,3-Dihydro-2-(phenylseleno)benzindol-5(4H)-one

Refernces

Total synthesis of brevisamide

10.1021/ol9015755

The study presents the second total synthesis of Brevisamide, a marine cyclic ether alkaloid derived from Karenia brevis. The streamlined synthesis was achieved in 21 steps with a 5.2% overall yield, featuring a key SmI2 reductive cyclization step to access the tetrasubstituted pyran core. Key chemicals used in the study include monobenzyl protected-1,4-butane diol, which served as the starting material for the synthesis of pyran 3; ethyl propiolate, used in the 1,4-addition to form intermediate 9; and phosphonate ester 2, synthesized through a series of reactions including a Wittig reaction and an Arbuzov reaction, which was crucial for the Horner-Wadsworth-Emmons reaction to assemble the western C1-C4 and eastern C5-C15 fragments. The purpose of these chemicals was to construct the complex structure of Brevisamide through a series of strategic synthetic steps, ultimately leading to the successful synthesis of the natural product.