methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate

Base Information

• Chemical Name: methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate
• CAS No.: 145353-91-9
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.274

Synonyms:methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate

Chemical Property of methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate

Chemical Property:

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Technology Process of methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate

There total 6 articles about methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate 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:

(1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one (68069-67-0) → methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate (145353-91-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaOAc, HOAc, CH₃CO₃H, 2) 2N H₂SO₄ / 1) 10 to 20 deg C 18 h, 2) RT, 2 h

2: 1) LDA / 1) THF, -60 to -70 deg C, 1 h, 2) -60 to -20 deg C, 2 h

3: 89 percent / DIBAL / tetrahydrofuran; hexane / 1 h / -70 °C

4: 1) n-BuLi / 1) DME, hexane, 5 deg C, 1 h, 2) DME, RT, 1 h

6: Jones' reagent / acetone / 1 h / Ambient temperature

7: diethyl ether / Ambient temperature

With peracetic acid; n-butyllithium; jones' reagent; sulfuric acid; sodium acetate; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; acetone;

Reference yield:

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one (145353-87-3) → methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate (145353-91-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / DIBAL / tetrahydrofuran; hexane / 1 h / -70 °C

2: 1) n-BuLi / 1) DME, hexane, 5 deg C, 1 h, 2) DME, RT, 1 h

4: Jones' reagent / acetone / 1 h / Ambient temperature

5: diethyl ether / Ambient temperature

With n-butyllithium; jones' reagent; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; acetone;

Reference yield:

(1S,6S,1'S)-(+)-2-(1'-methyl-2'-propenyl)-5-cyclohexen-1-ol (145353-89-5) → methyl (1S,4S,1'S)-(-)-4-(1'-methyl-2'-propenyl)-2-cyclohexenecarboxylate (145353-91-9)

Guidance literature:

Multi-step reaction with 3 steps

2: Jones' reagent / acetone / 1 h / Ambient temperature

3: diethyl ether / Ambient temperature

With jones' reagent; In diethyl ether; acetone;

upstream raw materials:

(1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one

(1S,6S,1'S)-(+)-2-(1'-methyl-2'-propenyl)-5-cyclohexen-1-ol

(3S,3aS,7aR)-(+)-methyl-2,3,3a,4,5,7a-hexahydrobenzfuran-2-one

(3aS,7aR)-(+)-2,3,3a,4,5,7a-hexahydrobenzofuran-2-one

Downstream raw materials:

(+)-(4R)-[(S)-1,5-dimethyl-3-oxohexyl]cyclohex-1-enecarboxylic acid methyl ester

methyl (1'R,4R)-4-(2'-formyl-1'-methylethyl)cyclohex-1-ene-1-carboxylate

methyl (4R,1'R)-(+)-4-(3'-hydroxypropyl)-1-cyclohexanecarboxylate

methyl (4R,1'R,3'RS)-(+)-4-(1',5'-dimethyl-3'-hydroxyhexyl)-1-cyclohexenecarboxylate

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