Marmelo oxide B

Base Information

• Chemical Name: Marmelo oxide B
• CAS No.: 92343-93-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• UNII: Q64KN7NJ8S
• Nikkaji Number: J146.597J
• Wikidata: Q105261088
• Mol file: 92343-93-6.mol

Synonyms:Marmelo oxide B;(+)-Marmelo oxide B;Marmelo oxide B, (+)-;Q64KN7NJ8S;92343-93-6;(2S,4R)-Tetrahydro-4-methyl-2-[(1E)-3-methyl-1,3-butadien-1-yl]furan;Furan, tetrahydro-4-methyl-2-(3-methyl-1,3-butadienyl)-, [2S-[2alpha(E),4beta]]-;Furan, tetrahydro-4-methyl-2-[(1E)-3-methyl-1,3-butadien-1-yl]-, (2S,4R)-

Chemical Property of Marmelo oxide B

Chemical Property:

• PSA: 9.23000
• LogP: 2.54370
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC(OC1)C=CC(=C)C
• Isomeric SMILES: C[C@@H]1C[C@H](OC1)/C=C/C(=C)C

Technology Process of Marmelo oxide B

There total 38 articles about Marmelo oxide B 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: 60.0%

(2S,4R,5E)-2,7-Dimethyl-5,7-octadien-1,4-diol (89102-91-0) → marmelo oxide A (89103-56-0,92343-93-6)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 20 ℃;

Reference yield:

(2R,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (74183-60-1) → 3,5-cis-marmelo oxide (89103-56-0,92343-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran

2: TsCl, pyridine

With pyridine; lithium aluminium tetrahydride; p-toluenesulfonyl chloride; In tetrahydrofuran;

Reference yield:

(2R,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (74183-60-1) → 3,5-trans-marmelo oxide (89103-56-0,92343-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran

2: TsCl, pyridine

With pyridine; lithium aluminium tetrahydride; p-toluenesulfonyl chloride; In tetrahydrofuran;

upstream raw materials:

2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran

2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran

2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran

(E)-2-methyl-3,5-hexadien-2-ol

Refernces

• 1、 Srikrishna, A.,Krishnan, K.. "Synthesis of (+/-)-Marmelo Oxides by a Radical Cyclization Reaction". . p. 3981 - 3983. Retrieved 2007/10/02.
• 2、 Nishida, Yoshihiro,Ohrui, Hiroshi,Meguro, Hiroshi. "Absolute Configurations of Marmelo Oxides". . p. 2969 - 2972. Retrieved 2007/10/02.