105231-06-9

Basic information

• Product Name: (1S,2R,3R)-3-(3-tert-Butoxycarbonyl-propyl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester
• CAS NO: 105231-06-9
• Molecular Weight: 340.417
• Mol File: 105231-06-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R,3R)-3-(3-tert-Butoxycarbonyl-propyl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3R)-3-(3-tert-Butoxycarbonyl-propyl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester(105231-06-9)
• EPA Substance Registry System: (1S,2R,3R)-3-(3-tert-Butoxycarbonyl-propyl)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester(105231-06-9)

Safety Data

• Hazardous Substances Data: 105231-06-9(Hazardous Substances Data)

Upstream product

• 6182-78-1 tert-butyl 4-iodobutanoate 
• 186581-53-3 diazomethane 
• 108-31-6 maleic anhydride 
• 67-56-1 methanol 
• 87240-90-2 4-(1,1-Dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-butyric acid tert-butyl ester 

Relevant articles and documents

Stereoselective Synthesis of (E)-, (E,Z)-, and (E,E)-Conjugated Dienes via Alkylation of 3-Sulfolenes as the Key Step

A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step.Direct alkylation of 3-sulfolene at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78 deg C.Alkylation of 2-alkyl-3-sulfolenes gives trans-2,5-dialkyl-3-sulfolenes with 100percent regioselectivity and more than 90percent stereoselectivity.Desulfonylation of trans-3,5-disubstituted 3-sulfolenes is examined in detail, and the conditions to give stereoselectively the corresponding (E,Z)-and (E,E)-conjugated dienes are found.Applying the method, three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, are easily synthesized by starting with 3-sulfolene with nearly 100percent stereoselectivity.Synthesis of cis-3,4,5-trisubstituted cyclohexenes using 2-substituted 3-sulfolenes as the diene synthons is also described.