8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octane

Base Information

• Chemical Name: 8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octane
• CAS No.: 19901-96-3
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• Mol file: 19901-96-3.mol

Synonyms:

Chemical Property of 8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octane

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octane

There total 9 articles about 8,8-Dimethyl-2-methylene-6-oxabicyclo[3.2.1]octane 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: 81.0%

(1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol (72445-03-5,85121-46-6) → (+/-)-Karahana ether (19901-96-3,22922-43-6,106160-64-9,143562-84-9)

Guidance literature:

With p-toluenesulfonyl chloride; In pyridine; at 0 ℃; for 5h;

Reference yield:

methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate (85121-45-5) → (+/-)-Karahana ether (19901-96-3,22922-43-6,106160-64-9,143562-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 0 - 25 °C

2: 81 percent / TsCl, pyridine / 5 h / 0 - 25 °C

With pyridine; lithium aluminium tetrahydride; p-toluenesulfonyl chloride; In diethyl ether;

Reference yield:

methyl(Z)-6,7-epoxy-7-methyl-3-<(trimethylsilyl)methyl>-2-octenoate (103142-50-3) → (+/-)-Karahana ether (19901-96-3,22922-43-6,106160-64-9,143562-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂ / -56 °C

2: LiAlH₄ / diethyl ether / 0 - 25 °C

3: 81 percent / TsCl, pyridine / 5 h / 0 - 25 °C

With pyridine; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; p-toluenesulfonyl chloride; In diethyl ether; dichloromethane;

upstream raw materials:

(1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol

methyl cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanecarboxylate

methyl(Z)-6,7-epoxy-7-methyl-3-<(trimethylsilyl)methyl>-2-octenoate

methyl (Z)-7-methyl-3-((trimethylsilyl)methyl)octa-2,6-dienoate

Refernces

• 1、 Barrero, Alejandro F.,Alvarez-Manzaneda, Enrique J.,Palomino, P. Linares. "Synthesis of (+/-)-Karahana Ether and Karahanaenone by Selective Cyclization of 6,7-Epoxygeranyl Acetate". . p. 13239 - 13250. Retrieved 2007/10/02.
• 2、 Armstrong, Rosemary J.,Weiler, Larry. "Stereoselective cyclization of epoxy allylsilanes. A synthesis of karahana ether". . p. 214 - 216. Retrieved 2007/10/02.