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

Base Information

Chemical Name:(1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone
CAS No.:82873-82-3
Molecular Formula:C₂₁H₂₆O₄
Molecular Weight:342.435
Hs Code.:

Synonyms:

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

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

There total 15 articles about (1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone 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: 99.0%

: 82873-81-2,127060-83-7
(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

: 82873-82-3,127060-84-8
(1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone

Guidance literature:: With Hg(II) salt; for 0.166667h; Ambient temperature;
DOI:10.1016/0040-4020(84)85126-1

Reference yield:

: 82873-73-2
(2aS,4R,4aS,6aS,6bR)-2-Hydroxy-6,6-dimethyl-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

: 82873-82-3,127060-84-8
(1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone

Guidance literature:: Multi-step reaction with 14 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

14: 99 percent / Hg(II) salt / 0.17 h / Ambient temperature

With pyridine; aluminium hydride; lead(IV) acetate; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; copper diacetate; Hg(II) salt; 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

Reference yield:

: 82873-76-5,90546-14-8
(3aRS,6SR,6aRS)-3,3a,4,5,6,6a-hexahydro-6-hydroxy-5,5-dimethyl-1-pentalenecarboxylic acid methyl ester

: 82873-82-3,127060-84-8
(1SR,3aRS,6RS,6aRS)-1-acetonyl-6-benzoyloxy-1,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(3H)-pentalenone

Guidance literature:: Multi-step reaction with 11 steps

1: 92 percent / Jones reagent / acetone / 0.5 h / 0 °C

2: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

3: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

4: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

5: 95 percent / pyridine / 12 h / 0 °C

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

7: 96 percent / pyridine / 6 h / Ambient temperature

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

9: 78 percent / Jones reagent / acetone / 0.5 h / 0 °C

10: 80 percent / 1 M t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

11: 99 percent / Hg(II) salt / 0.17 h / Ambient temperature

With aluminium hydride; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; Hg(II) salt; borane; potassium tert-butylate; dihydrogen peroxide; 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