(1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

Base Information

• Chemical Name: (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon
• CAS No.: 127060-83-7
• Molecular Formula: C₂₁H₂₅ClO₃
• Molecular Weight: 360.881
• Mol file: 127060-83-7.mol

Synonyms:(1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

Chemical Property of (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

There total 32 articles about (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon 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: 80.0%

2,3-Dichloroprop-1-ene (78-88-6) + 6α-benzoyloxy-4β,7,7-trimethyl-1α,5α-bicyclo<3.3.0>octan-3-one (82881-09-2,89064-08-4,127060-82-6) → (1SR,3aRS,6RS,6aRS)-6-benzoyloxy-1-(2-chloro-2-propenyl)-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone (82873-81-2,127060-83-7)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; benzene; Heating;

DOI:10.1016/0040-4020(84)85126-1

Reference yield: 63.0%

2,3-Dichloroprop-1-ene (78-88-6) + (1R,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon (127060-82-6) → (1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon (127060-83-7)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; benzene; at 80 ℃; for 1.5h;

Reference yield:

(2aS,4R,4aS,6aS,6bR)-2-Hydroxy-6,6-dimethyl-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde (82873-73-2) → (1SR,3aRS,6RS,6aRS)-6-benzoyloxy-1-(2-chloro-2-propenyl)-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone (82873-81-2,127060-83-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 84 percent / Jones reagent / acetone / 1 h

2: 1.) pyridine, Cu(OAc)2; 2.) Pb(OAc)4 / 1.) benzene, 30 min; 2a.) 2.5 h, dark, b.) benzene, reflux, 30 min

3: 1.) t-AmONa; 2.) water / 1.) DMSO, 18 h, r.t.; 2.) 6 h; 3.) 24 h

4: 92 percent / Jones reagent / acetone / 0.5 h / 0 °C

5: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

6: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

7: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

8: 95 percent / pyridine / 12 h / 0 °C

9: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

10: 96 percent / pyridine / 6 h / Ambient temperature

11: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

12: 78 percent / Jones reagent / acetone / 0.5 h / 0 °C

13: 80 percent / 1 M t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

With pyridine; aluminium hydride; lead(IV) acetate; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; copper diacetate; borane; potassium tert-butylate; water; dihydrogen peroxide; sodium tert-pentoxide; methanesulfonyl chloride; lithium chloride; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4020(84)85126-1

upstream raw materials:

2,3-Dichloroprop-1-ene

(1R,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

(1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol

(6R,7R)-(-)-7-Hydroxy-3-oxabicyclo<4.3.0>non-1-en-9-on

Downstream raw materials:

(1S,3aR,6R,6aR)-(-)-6-Benzoyloxy-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-1-(2-oxopropyl)-2(1H)-pentalenon

(-)-Hypnophilin

(3aS,3bR,4R,6aS)-(-)-6-(Benzoyloxy)-3,3a,3b,4,5,6,6a,7-octahydro-3a,5,5-trimethyl-2H-cyclopentapentalen-2-on

(1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone