(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

Base Information

Chemical Name:(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one
CAS No.:153141-24-3
Molecular Formula:C₂₀H₂₅NO₃S
Molecular Weight:359.489
Hs Code.:

Synonyms:(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

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Chemical Property of (-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

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Technology Process of (-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

There total 9 articles about (-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-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: 95.0%

: 15851-89-5,13565-07-6
(E)-p-methylcinnamoyl chloride

: 94594-90-8,124224-04-0
(2R)-bornane-10,2-sultam

: 153141-24-3
(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

Guidance literature:: (2R)-bornane-10,2-sultam; With sodium hydride; In toluene; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

(E)-p-methylcinnamoyl chloride; In toluene; mineral oil; at 0 - 20 ℃; for 18h;
DOI:10.1002/hlca.201100197

Reference yield:

: 153897-28-0
(R)-2-amino-3-cyano-6-methyl-5-(N-oxobornane-10,2-sultam)-4-phenyl-4H-pyran

: 153141-24-3
(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 3 h / 0 °C

2: 82 percent / toluene / 1 h / 130 °C

3: piperidine / toluene / Ambient temperature

With piperidine; lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4020(01)87029-0

Reference yield:

: 153897-33-7
(R)-2-amino-4-(p-chlorophenyl)-3-cyano-6-methyl-5-(N-oxobornane-10,2-sultam)-4H-pyran

: 153141-24-3
(-)-(2E)-3-(4-methylphenyl)-1-[(3aS,6R,7aR)tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]prop-2-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: LiAlH₄ / diethyl ether; tetrahydrofuran / 3 h / 0 °C

2: 82 percent / toluene / 150 °C

3: piperidine / toluene / Ambient temperature

With lithium aluminium tetrahydride; piperidine; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4039(00)73900-1