(1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate

Base Information

• Chemical Name: (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate
• CAS No.: 104898-08-0
• Molecular Formula: C₂₆H₄₃NO₄S
• Molecular Weight: 465.698
• Mol file: 104898-08-0.mol

Synonyms:(1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate

Chemical Property of (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate

There total 12 articles about (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate 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: 93.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate (104898-08-0)

Guidance literature:

With silver cyanide; In benzene; for 5h; Heating;

Reference yield:

(R)-3,4-Dimethyl-pent-4-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester → (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate (104898-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1N NaOH / aq. ethanol / Heating

2: AgCN / benzene / 4 h / Heating

3: 1.) CuI*P(Bu)3; 2.) Et₂O*BF₃ / 1.) -78 deg C, 30 min, Et₂O; 2.) Et₂O-THF (4:1) -78 to -40 deg C, 20 h

4: 1N NaOH / aq. ethanol / Heating

5: AgCN / benzene / 4 h / Heating

With sodium hydroxide; silver cyanide; CuI*P(n-Bu)3; boron trifluoride diethyl etherate; In ethanol; benzene;

DOI:10.1002/hlca.19850680126

Reference yield:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → (1S,2R,4R)-1-(N,N-dicyclohexylaminosulfonylmethyl)-7,7-dimethylbicyclo<2.2.1>heptan-2-yl crotonate (104898-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1: AgCN / benzene / 4 h / Heating

2: 1.) CuI*P(Bu)3; 2.) Et₂O*BF₃ / 1.) -78 deg C, 30 min, Et₂O; 2.) Et₂O-THF (4:1) -78 to -40 deg C, 20 h

3: 1N NaOH / aq. ethanol / Heating

4: AgCN / benzene / 4 h / Heating

With sodium hydroxide; silver cyanide; CuI*P(n-Bu)3; boron trifluoride diethyl etherate; In ethanol; benzene;

DOI:10.1002/hlca.19850680126

upstream raw materials:

trans-chrotonyl chloride

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

<(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>propionate

(E)-Hex-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Downstream raw materials:

(R)-3-Methyl-pent-4-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(S)-3-Methyl-hexanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(R)-6-Isopropenyl-3-methyl-dec-9-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(-)-10-dicyclohexylsulfamoyl-D-isoborneol