cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

Base Information

Chemical Name:cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one
CAS No.:110366-72-8
Molecular Formula:C₉H₁₄O₂
Molecular Weight:154.209
Hs Code.:

Synonyms:

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Chemical Property of cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

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Technology Process of cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

There total 2 articles about cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-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: 65.0%

: 110366-63-7
(S)-3-Methyl-3-((E)-3-p-tolylsulfanyl-allyl)-cyclopentanone

: 110366-72-8,110366-73-9,131615-14-0,142619-48-5
cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

: 110366-70-6,110366-71-7
cis-8-(formyloxy)-5-methylbicyclo<3.3.0>octan-2-one

: 110366-74-0
3-methyl-3-<3,3-bis-(p-tolylthio)propyl>cyclopentanone

Guidance literature:: With formic acid; trifluoroacetic acid; at 70 ℃; for 3h;
DOI:10.1021/jo00381a002

Reference yield: 10.0%

: 64-18-6
formic acid

: 110366-63-7
(S)-3-Methyl-3-((E)-3-p-tolylsulfanyl-allyl)-cyclopentanone

: 110366-72-8,110366-73-9,131615-14-0,142619-48-5
cis-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

: 110366-70-6,110366-71-7
cis-8-(formyloxy)-5-methylbicyclo<3.3.0>octan-2-one

: 110366-74-0
3-methyl-3-<3,3-bis-(p-tolylthio)propyl>cyclopentanone

Guidance literature:: With trifluoroacetic acid; at 70 ℃; for 3h;
DOI:10.1021/jo00381a002

Reference yield:

: 110366-72-8,110366-73-9,131615-14-0,142619-48-5
(1R*,5S*,8S*)-8-hydroxy-5-methylbicyclo<3.3.0>octan-2-one

: 131556-26-8,131615-18-4
methyl (1R*,2S*,3R*,5R*,8S*,9R*)-2,5,9-trimethyl-3-phenylselenyl-4-oxotricyclo<6.3.0.0^1,5>undecane-3-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 2) hexamethylphosphoric triamide (HMPT) / THF, Et₂O, 1) 1.1) -78 deg C, 1.5 h, 1.2) -48 deg C, 2.5 h, 2) 2.1) -48 deg C, to RT, 1.5 h, 2.2) RT, 45 min

4: 1) BH₃, 2) 30percent aq. H₂O₂, 3N NaOH / 1) THF, RT, 2 h , 2) THF, MeOH, reflux, 1,5 h

5: 1) oxalyl chloride, 2) Et₃N / DMSO, CH₂Cl₂, 1) -78 deg C, 1 h, 2) 0 deg C, 1 h

6: 85 percent / Et₂O*BF₃ / CH₂Cl₂ / 1 h / 0 °C

7: 74 percent / Raney nickel (W-4) / acetone / 1.5 h / Ambient temperature

8: 1) LDA / THF, 1) -78 deg C, 1 h, 2) RT, 1 h

9: 88 percent / Pd(OAc)2 / acetonitrile / 3.8 h / Ambient temperature

10: 96 percent / diethyl ether; tetrahydrofuran / 1.5 h / -78 °C

11: 88 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

12: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / Ambient temperature

13: 1) LDA, 2) HMPT / THF, 1) -78 deg C, 50 min., 2) -78 deg C, 90 min.

14: 1) LDA / THF, 1) -78 deg C, 40 min., 2) -78 deg C, 25 min.

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hydroxide; oxalyl dichloride; Raney nickel (W-4); boron trifluoride diethyl etherate; borane; hydrogen; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile;
DOI:10.1055/s-1992-34160