6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI)

Base Information

• Chemical Name: 6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI)
• CAS No.: 676121-67-8
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol file: 676121-67-8.mol

Synonyms:6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI)

Chemical Property of 6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI)

Chemical Property:

• PSA: 12.53000
• LogP: 2.80600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI)

There total 9 articles about 6H-Indeno[1,2-b]oxirene,1a,6a-dihydro-2-(1-methylethyl)-(9CI) 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: 86.0%

4-isopropyl-1-indene (152685-98-8) → 2-isopropyl-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene (676121-67-8)

Guidance literature:

With Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/jo049381f

Reference yield:

4-hydroxy-5-methyl-hexan-2-one (65651-63-0,38836-21-4) → 2-isopropyl-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene (676121-67-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 71 percent / p-TsOH*H₂O; Na₂SO₄ / benzene / 5 h / 90 °C

2: 79 percent / LiN(TMS)2 / tetrahydrofuran; toluene / 1.17 h / -78 - 20 °C

3: 2,5-di-tert-butylhydroquinone / benzene / 56 h / 200 °C

4: p-TsOH*H₂O / acetone / 0.5 h / 20 °C

5: 75 percent / p-cymene / Pd/C / 45 h / 200 °C

6: 97 percent / NaH / tetrahydrofuran / 2.5 h / 20 °C

7: 87 percent / NaBH₄; NiCl₂*6H₂O / methanol / 3 h / 0 - 20 °C

8: 100 percent / pTsOH*H₂O / benzene / 0.67 h / 20 - 100 °C

9: 86 percent / mCPBA; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; N-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / -78 °C

With sodium tetrahydroborate; 4-methylisopropylbenzene; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene; 3: Diels-Alder reaction / 9: Jacobsen reaction;

DOI:10.1021/jo049381f

Reference yield:

(E)-4-isopropylbut-3-en-2-one (1669-43-8,5166-53-0,1821-29-0) → 2-isopropyl-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene (676121-67-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / LiN(TMS)2 / tetrahydrofuran; toluene / 1.17 h / -78 - 20 °C

2: 2,5-di-tert-butylhydroquinone / benzene / 56 h / 200 °C

3: p-TsOH*H₂O / acetone / 0.5 h / 20 °C

4: 75 percent / p-cymene / Pd/C / 45 h / 200 °C

5: 97 percent / NaH / tetrahydrofuran / 2.5 h / 20 °C

6: 87 percent / NaBH₄; NiCl₂*6H₂O / methanol / 3 h / 0 - 20 °C

7: 100 percent / pTsOH*H₂O / benzene / 0.67 h / 20 - 100 °C

8: 86 percent / mCPBA; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; N-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / -78 °C

With sodium tetrahydroborate; 4-methylisopropylbenzene; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene; 2: Diels-Alder reaction / 8: Jacobsen reaction;

DOI:10.1021/jo049381f

upstream raw materials:

4-isopropyl-1-indene

4-hydroxy-5-methyl-hexan-2-one

(E)-4-isopropylbut-3-en-2-one

5-methyl-2-trimethylsilyloxy-1,3(E)-hexadiene

Downstream raw materials:

5-isopropyl-4-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-1,9,9a,10a-tetrahydro-4H,4bH-10-oxa-4a-aza-indeno[1,2-a]indene-2-carboxylic acid ethyl ester

1-{4-hydroxymethyl-6-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-3,6-dihydro-2H-pyridin-1-yl}-7-isopropyl-indan-2-ol

5-isopropyl-4-phenyl-1,9,9a,10a-tetrahydro-4H,4bH-10-oxa-4a-aza-indeno[1,2-a]indene-2-carboxylic acid ethyl ester

(1S,2R)-(-)-cis-1-[(2R)-4-hydroxymethyl-2-phenyl-1,2,5,6-tetrahydropyridin-1-yl]-7-isopropylindan-2-ol