(+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol

Base Information

• Chemical Name: (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol
• CAS No.: 80113-04-8
• Molecular Formula: C₁₃H₂₂O₂S₂
• Molecular Weight: 274.448
• Mol file: 80113-04-8.mol

Synonyms:(+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol

Chemical Property of (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol

There total 19 articles about (+/-)-1-(1,3-dithianyl)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enol 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: 78.0%

(4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol (123331-89-5,123408-94-6,137036-88-5,137036-89-6) → (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol (67119-86-2,67119-87-3,80113-04-8,123408-90-2,123408-91-3,135503-46-7,135503-47-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1021/jo00284a011

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4S)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol (67119-86-2,67119-87-3,80113-04-8,123408-90-2,123408-91-3,135503-46-7,135503-47-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / Zn(OAc)2, BF₃*Et₂O / 10 h / 10 °C

2: 1) Pd(OAc)2, 1,2-bis(diphenylphosphino)ethane, allyl ethyl carbonate, 2) tri-n-butyltin methoxide / 1) CH₃CN, 20 min, 2) reflux, 7 h

3: 1) n-BuLi / 1) THF, hexane, -30 deg C, 1.5 h, 2) room temperature, 0.5 h

With palladium diacetate; n-butyllithium; allyl ethyl carbonate; boron trifluoride diethyl etherate; zinc diacetate; tributyltin methoxide; 1,2-bis-(diphenylphosphino)ethane;

DOI:10.1021/jo00024a031

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4R)-1-(1,3-dithianyl)-4-(2-(2-hydroxypropanyl))-2-cyclohexen-1-ol (67119-86-2,67119-87-3,80113-04-8,123408-90-2,123408-91-3,135503-46-7,135503-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / BF₃*OEt₂, Zn(OAc)2

2: allyl ethyl carbonate, Pd(OAc)2, bis(diphenylphosphino)ethane, Bu₃SnOMe

3: tetrahydrofuran

4: LAH

With palladium diacetate; lithium aluminium tetrahydride; allyl ethyl carbonate; boron trifluoride diethyl etherate; zinc diacetate; tributyltin methoxide; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran;

DOI:10.1039/c39910000692

upstream raw materials:

(4R)-1-(1,3-dithianyl)-4-(2-propenylepoxy)-2-cyclohexen-1-ol

L-perillaldehyde

(R)-(+)-4-(2-propenyl)-2-cyclohexen-1-one

(R)-4-(2-Methyl-oxiranyl)-cyclohex-2-enone

Downstream raw materials:

(+/-)-11-hydroxy-Δ⁹-tetrahydrocannabinol

(6aR,10aR)-9-[1,3]Dithian-2-yl-6,6-dimethyl-1-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-3-ol

(+/-)-9-normethyl-9-(1,3-dithianyl)-Δ⁹-tetrahydrocannabinol

2-((1R,6R)-3-[1,3]Dithian-2-yl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol