(1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

Base Information

• Chemical Name: (1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one
• CAS No.: 226219-94-9
• Molecular Formula: C₂₁H₂₄O₂S
• Molecular Weight: 340.486

Synonyms:(1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

Chemical Property of (1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

Chemical Property:

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Technology Process of (1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

There total 1 articles about (1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one 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:

(+)-(S)-1-hexynyl p-tolyl sulfoxide (61783-64-0) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → 5-(1-hydroxybutyl)tricyclo<5.2.1.02,6>deca-4,8-dien-3-one + 5-(1-hydroxybutyl)tricyclo<5.2.1.02,6>deca-4,8-dien-3-one + (1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.02,6>deca-4,8-dien-3-one (226219-94-9) + (1R,2R,6S,7S)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.02,6>deca-4,8-dien-3-one (226219-96-1)

Guidance literature:

Yield given; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) toluene, RT, 30 min, 2.) toluene, 65 deg C, 27 h;

DOI:10.1016/S0957-4166(99)00032-4

Reference yield: 70.0%

(1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.02,6>deca-4,8-dien-3-one (226219-94-9) → (1S,2S,6R,7R)-4-butyl-5-p-tolylsulfanyltricyclo<5.2.1.02,6>deca-4,8-dien-3-one (226220-08-2)

Guidance literature:

With trifluoroacetic anhydride; sodium iodide; In acetone; at -40 ℃;

DOI:10.1016/S0957-4166(99)00032-4

Reference yield:

(1S,2S,6R,7R)-4-butyl-5-<(S)-4-tolylsulfinyl>tricyclo<5.2.1.02,6>deca-4,8-dien-3-one (226219-94-9) → (3aR,4R,7S,7aS)-2-Butyl-3-p-tolylsulfanyl-3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / NaI, trifluoroacetic anhydride / acetone / -40 °C

2: DIBALH / diethyl ether; hexane / -60 °C

With diisobutylaluminium hydride; trifluoroacetic anhydride; sodium iodide; In diethyl ether; hexane; acetone;

DOI:10.1016/S0957-4166(99)00032-4

upstream raw materials:

(+)-(S)-1-hexynyl p-tolyl sulfoxide

bicyclo[2.2.1]hepta-2,5-diene

Downstream raw materials:

(1S,2S,6R,7R)-4-butyl-5-p-tolylsulfanyltricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

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