5β-Acetoxy-2,2a,4aα,5,6,7,7aα,8,10bβ,10c-decahydro-2aβ,7α,10,10cβ-tetramethylnaphtho[2,1,8-cde]azulene-3(4H)-one

Base Information

Chemical Name:5β-Acetoxy-2,2a,4aα,5,6,7,7aα,8,10bβ,10c-decahydro-2aβ,7α,10,10cβ-tetramethylnaphtho[2,1,8-cde]azulene-3(4H)-one
CAS No.:65118-74-3
Molecular Formula:C₂₂H₃₀O₃
Molecular Weight:342.478
Hs Code.:
Mol file:65118-74-3.mol

Synonyms:Naphth[2,1,8-cde]azulen-3(2aH)-one,5-(acetyloxy)-2,4,4a,5,6,7,7a,8,10b,10c-decahydro-2a,7,10,10c-tetramethyl-,[2aS-(2aa,4ab,5a,7b,7ab,10ba,10ca)]-; Kempene 2; Kempene II; NK 2(terpene)

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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 5β-Acetoxy-2,2a,4aα,5,6,7,7aα,8,10bβ,10c-decahydro-2aβ,7α,10,10cβ-tetramethylnaphtho[2,1,8-cde]azulene-3(4H)-one

Chemical Property:

PSA：43.37000
LogP:4.47200

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 5β-Acetoxy-2,2a,4aα,5,6,7,7aα,8,10bβ,10c-decahydro-2aβ,7α,10,10cβ-tetramethylnaphtho[2,1,8-cde]azulene-3(4H)-one

There total 34 articles about 5β-Acetoxy-2,2a,4aα,5,6,7,7aα,8,10bβ,10c-decahydro-2aβ,7α,10,10cβ-tetramethylnaphtho[2,1,8-cde]azulene-3(4H)-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: 91.0%

: 1291100-99-6
C₂₀H₂₈O₂

: 108-24-7
acetic anhydride

: 65118-74-3
Kempen-2

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1002/anie.201007551

Reference yield: 32.0%

: 135041-61-1
Acetic acid (3aR,5aS,6R,8R,9S,9aS,9bR)-1-acetyl-3a,8,9a-trimethyl-4-oxo-9-(2-oxo-ethyl)-3a,4,5,5a,6,7,8,9,9a,9b-decahydro-3H-cyclopenta[a]naphthalen-6-yl ester

: 65118-74-3,135096-60-5
(+/-)-kempene-2

Guidance literature:: With TiCl₃-1,2-dimethoxyethane; copper; zinc; In 1,2-dimethoxyethane; for 2h; Heating;
DOI:10.1021/ja00015a064

Reference yield:

: 527-61-7
2,6-dimethyl-1,4-benzoquinone

: 65118-74-3,135096-60-5
(+/-)-kempene-2

Guidance literature:: Multi-step reaction with 21 steps

1: 1.) BF₃*Et₂O, 2.) Zn, HOAc / 1.) 96 h, 2.) reflux, 18 h

2: 1.) L-Selectride, 2.) NaOH, H₂O₂ / 1.) THF, -78 deg C, 2.) THF, 0 deg C

3: 83 percent / NaH, Bu₄NI / tetrahydrofuran / 72 h

4: 1.) sec-BuLi / 1.) THF, from -60 deg C to -20 deg C, 1 h, 2.) THF, -40 deg C, 30 min

5: ethanol

6: 1.) KOtBu / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 18 h

7: disiamylborane / tetrahydrofuran / 72 h / 40 °C

8: H₂O₂, NaOH / 0 °C

9: 98 percent / NaH, Bu₄NI / tetrahydrofuran / 48 h

10: 1.) BH₃*THF, 2.) NaOH, H₂O₂ / 1.) 0 deg C, 6 h

11: 90 percent / (COCl)2, DMSO / CH₂Cl₂

12: 1.) pyridinium bromide perbromide, 2.) LiBr, Li₂CO₃ / 1.) THF, -78 deg C, 30 min, 2.) DMF, 120 deg C, 16 h

13: 66 percent / EtAlCl₂ / toluene / 24 h / 80 °C

14: 95 percent / (CH₃)3NO / OsO₄ / acetone; H₂O

15: 88 percent / H₂ / 10percent Pd/C / ethyl acetate

16: 81 percent / NaIO₄ / dioxane; H₂O

17: 61 percent / TsOH*H₂O / benzene / 2 h / 80 °C

18: 66 percent / pyridine, DMAP

19: 68 percent / HCl / ethanol / 2 h / 80 °C

20: 57 percent / PCC/Al₂O₃ / hexane; CH₂Cl₂

21: 32 percent / TiCl₃*1.5DME, Zn-Cu / 1,2-dimethoxy-ethane / 2 h / Heating

With pyridine; hydrogenchloride; dmap; aluminum oxide; sodium hydroxide; sodium periodate; borane-THF; oxalyl dichloride; TiCl₃-1,2-dimethoxyethane; trimethylamine-N-oxide; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dihydrogen peroxide; sec.-butyllithium; pyridinium hydrobromide perbromide; ethylaluminum dichloride; bis-(1,2-dimethylpropyl)borane; tetra-(n-butyl)ammonium iodide; lithium carbonate; L-Selectride; copper; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; pyridinium chlorochromate; lithium bromide; zinc; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene;
DOI:10.1021/ja00015a064