1H-Indene,4-(1-methylethyl)-(9CI)

Base Information

• Chemical Name: 1H-Indene,4-(1-methylethyl)-(9CI)
• CAS No.: 152685-98-8
• Molecular Formula: C12H14
• Molecular Weight: 158.243
• Mol file: 152685-98-8.mol

Synonyms:1H-Indene,4-(1-methylethyl)-(9CI)

Chemical Property of 1H-Indene,4-(1-methylethyl)-(9CI)

Chemical Property:

• PSA: 0.00000
• LogP: 3.37930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indene,4-(1-methylethyl)-(9CI)

There total 1 articles about 1H-Indene,4-(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:

4-hydroxy-5-methyl-hexan-2-one (65651-63-0,38836-21-4) → 4-isopropyl-1-indene (152685-98-8)

Guidance literature:

Multi-step reaction with 8 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

With sodium tetrahydroborate; 4-methylisopropylbenzene; 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; sodium hydride; toluene-4-sulfonic acid; sodium sulfate; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; acetone; toluene; benzene; 3: Diels-Alder reaction;

DOI:10.1021/jo049381f

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-isopropyl-1-indene (152685-98-8) → (1S,2R)-(-)-cis-1-[(2R)-4-hydroxymethyl-2-phenyl-1,2,5,6-tetrahydropyridin-1-yl]-7-isopropylindan-2-ol (461641-20-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / mCPBA; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; N-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / -78 °C

2.1: H₂SO₄; acetonitrile / hexane / 1 h / 20 °C

2.2: 39 percent / H₂O / 2 h / 100 °C

3.1: CHCl₃ / 3 h / 24 °C

4.1: 1.12 g / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.08 h / 20 °C

With lithium aluminium tetrahydride; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; sulfuric acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; acetonitrile; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; 1.1: Jacobsen reaction / 2.1: Ritter reaction;

DOI:10.1021/jo049381f

upstream raw materials:

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

Downstream raw materials:

(1S,2R)-(-)-cis-1-amino-7-isopropylindan-2-ol

2-isopropyl-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene

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

Refernces

• 1、 Tanaka, Katsunori,Kobayashi, Toyoharu,Mori, Hajime,Katsumura, Shigeo. "Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine". . p. 5906 - 5925. Retrieved 2007/10/03.