(1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

Base Information

Chemical Name:(1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one
CAS No.:151053-00-8
Molecular Formula:C₁₉H₂₄OS
Molecular Weight:300.465
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

Chemical Property:

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Technology Process of (1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

There total 1 articles about (1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-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:

: 128261-64-3
(1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one

: 7103-09-5
4-but-1-enylmagnesium bromide

: 151053-00-8
(1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

Guidance literature:: copper(l) iodide; In tetrahydrofuran; at -50 - -40 ℃; for 1h;
DOI:10.1021/jo00071a025

Reference yield:

: 151053-00-8
(1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

: (2RS,4aR,5R)-4-(1-Hydroxy-1-methylethyl)-4a,5-dimethyl-2-(phenylseleno)-3,4,4a,5,6,7-hexahydronaphthalen-1(2H)-one

Guidance literature:: Multi-step reaction with 17 steps

1: m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

2: MsOH, Ac₂O / 1.) 0 deg C, 1 h, 2.) r.t., 15 h

3: m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

4: K₂CO₃, Cs₂CO₃ / acetonitrile / Ambient temperature

5: 90 percent / CuI / diethyl ether; tetrahydrofuran / 1 h

6: 89 percent / 6percent Na(Hg) / methanol / 1.5 h / -50 - -20 °C

7: 1.) diborane, 2.) 30percent aq. H₂O₂, 3 M aq. NaOH / 1.) THF, 0 deg C, 5 h; r.t., 15 h, 2.) 0 deg C, 4 h; r.t., 20 h

8: 92 percent / (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

9: 50 percent / t-BuOK / CH₂Cl₂ / 0.17 h / Ambient temperature

10: 80 percent / Zn(OAc)2, BF₃*Et₂O / 1.) 0 deg C, 10 min, 2.) r.t., 24 h

11: 1.) MeLi, 2.) Et₃N, HMPA / 1.) ether, -78 deg C, 30 min, 2.) -78 to 0 deg C, 3 h

12: Pd(OAc)2 / acetonitrile / 20 h / Ambient temperature

13: 69 percent / m-CPBA / CH₂Cl₂

14: 42 percent / LiBEt₃H

15: 84 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) reflux, 4 h

16: 98 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

17: 66 percent / LHMDS, HMPA / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 3 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dipyridinium dichromate; sodium amalgam; oxalyl dichloride; methanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; zinc diacetate; methyllithium; dihydrogen peroxide; acetic anhydride; lithium triethylborohydride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; diborane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo00071a025

Reference yield:

: 151053-00-8
(1R,3R,4S,5R)-4-But-3-enyl-6,6-dimethyl-3-phenylsulfanyl-bicyclo[3.1.1]heptan-2-one

: (1R,3R,4S,5R)-3-Benzenesulfonyl-4-but-3-enyl-6,6-dimethyl-bicyclo[3.1.1]heptan-2-one

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1.) 0 deg C, 1 h, 2.) r.t., 30 min;
DOI:10.1021/jo00071a025