(R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

Base Information

• Chemical Name: (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
• CAS No.: 144017-65-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 144017-65-2.mol

Synonyms:

Chemical Property of (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

Chemical Property:

Purity/Quality:

>95% ^*data from raw suppliers

(R)-Stiripentol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-Stiripentol is an S-isomer of Stiripentol (S686825) which is an epilepsy drug. It has been used as co-therapy for treatment of epilepsy. It inhibits the enzymes responsible for metabolism of other anti-convulsant agents.

Technology Process of (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol

There total 5 articles about (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol 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: 15.0%

5-vinyl-1,3-benzodioxole (7315-32-4) + (3R)-(+)-4,4-dimethyl-1-penten-3-ol (24580-44-7) → (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol (144017-65-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; Inert atmosphere; Heating; Enzymatic reaction;

DOI:10.1016/j.tetasy.2013.02.006

Reference yield:

caffeic acid (331-39-5,501-16-6) → (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol (144017-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 18 h / Reflux

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Heating; Enzymatic reaction

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; 2: |Alkene (Olefin) Metathesis;

DOI:10.1016/j.tetasy.2013.02.006

Reference yield:

4,4-dimethylpent-1-en-3-ol (60041-31-8,61348-36-5,24580-44-7) → (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol (144017-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: lipase A from Candida antarctica immobilized on Immobead 150 / hexane / 9 h / 35 °C / Enzymatic reaction

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Heating; Enzymatic reaction

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lipase A from Candida antarctica immobilized on Immobead 150; In hexane; dichloromethane; 2: |Alkene (Olefin) Metathesis;

DOI:10.1016/j.tetasy.2013.02.006

upstream raw materials:

5-vinyl-1,3-benzodioxole

(3R)-(+)-4,4-dimethyl-1-penten-3-ol

caffeic acid

3,4-dihydroxystyrene

Refernces