(S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone

Base Information

• Chemical Name: (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone
• CAS No.: 131556-48-4
• Molecular Formula: C₁₅H₁₇NO₃S
• Molecular Weight: 291.371

Synonyms:(S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone

Chemical Property of (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone

Chemical Property:

Purity/Quality:

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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone

There total 3 articles about (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone 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:

1-((R)-3-Methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-propenone (131556-37-1) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (R)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-methanone (131556-32-6) + (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-methanone (131556-48-4)

Guidance literature:

With ethylaluminum dichloride; In dichloromethane; at -78 ℃; for 18h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)97793-1

Reference yield:

(R)-3-methyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide (130973-53-4) → (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-methanone (131556-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / NEt₃ / CH₂Cl₂ / 1 h / 0 °C

2: EtAlCl₂ / CH₂Cl₂ / 18 h / -78 °C

With ethylaluminum dichloride; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)97793-1

Reference yield:

(1R,2S)-Bicyclo[2.2.1]hept-5-en-2-yl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-methanone (131556-41-7,131556-42-8,135325-16-5) → (S)-Cyclohex-3-enyl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-methanone (131556-48-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent aq. H₂O₂, LiOH / tetrahydrofuran; H₂O / 0 °C

2: 66 percent / NEt₃ / CH₂Cl₂ / 1 h / 0 °C

3: EtAlCl₂ / CH₂Cl₂ / 18 h / -78 °C

With lithium hydroxide; dihydrogen peroxide; ethylaluminum dichloride; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4039(00)97793-1

upstream raw materials:

1-((R)-3-Methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-propenone

buta-1,3-diene

(R)-3-methyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide

(1R,2S)-Bicyclo[2.2.1]hept-5-en-2-yl-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-methanone

Downstream raw materials:

(1S)-3-cyclohexenecarboxylic acid

(R)-3-methyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide

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