(3S)-7-Bromo-1,2,3,8b-tetrahydro-3α,6,8bβ-trimethyl-3aH-cyclopenta[b]benzofuran-3aβ-carbaldehyde

Base Information

Chemical Name:(3S)-7-Bromo-1,2,3,8b-tetrahydro-3α,6,8bβ-trimethyl-3aH-cyclopenta[b]benzofuran-3aβ-carbaldehyde
CAS No.:64052-99-9
Molecular Formula:C₁₅H₁₇BrO₂
Molecular Weight:309.203
Hs Code.:
Mol file:64052-99-9.mol

Synonyms:3aH-Cyclopenta[b]benzofuran-3a-carboxaldehyde,7-bromo-1,2,3,8b-tetrahydro-3,6,8b-trimethyl-, [3S-(3a,3ab,8bb)]-; Aplysinal

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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 (3S)-7-Bromo-1,2,3,8b-tetrahydro-3α,6,8bβ-trimethyl-3aH-cyclopenta[b]benzofuran-3aβ-carbaldehyde

Chemical Property:

Boiling Point:375.3±42.0 °C(Predicted)
PSA：26.30000
Density:1.456±0.06 g/cm3(Predicted)
LogP:3.77520

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (3S)-7-Bromo-1,2,3,8b-tetrahydro-3α,6,8bβ-trimethyl-3aH-cyclopenta[b]benzofuran-3aβ-carbaldehyde

There total 15 articles about (3S)-7-Bromo-1,2,3,8b-tetrahydro-3α,6,8bβ-trimethyl-3aH-cyclopenta[b]benzofuran-3aβ-carbaldehyde 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: 96.0%

: rel-(3S,3aS,8bS)-[7-bromo-3,6,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3-yl]methanol

: 64052-99-9
rel-(3S,3aS,8bS)-7-bromo-3,6,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3a-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(00)01055-3

Reference yield:

: 6921-64-8
4'-hydroxy-2'-methylacetophenone

: 64052-99-9
rel-(3S,3aS,8bS)-7-bromo-3,6,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3a-carbaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1.1: 97 percent / KOH / acetone / 15 h / 20 °C

2.1: 76 percent / S₈ / 24 h / 100 °C

3.1: 90 percent / H₂O / tetrahydrofuran / 18 h / Heating

4.1: 54 percent / t-BuLi / tetrahydrofuran; pentane / 9 h / -78 - 20 °C

5.1: 81 percent / BCl₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: 84 percent / N-isopropylcyclohexylamine; s-BuLi; HMPA / tetrahydrofuran; cyclohexane / 1.5 h / -78 - 20 °C

7.1: titanocene dichloride / heptane / 24 h / 20 °C

7.2: 54 percent / heptane; tetrahydrofuran / 20.5 h / -78 - 20 °C

8.1: 28 percent / Bu₃SnH; AIBN / toluene / 18 h / Heating

9.1: 52 percent / m-CPBA / CH₂Cl₂ / 24 h / 0 °C

10.1: 57 percent / Br₂; NaHCO₃ / CHCl₃ / 1 h / 0 °C

11.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With sulfur; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; 2,2'-azobis(isobutyronitrile); titanocene dichloride; N-cyclohexylisopropylamine; water; bromine; tert.-butyl lithium; sec.-butyllithium; tri-n-butyl-tin hydride; boron trichloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; n-heptane; dichloromethane; chloroform; cyclohexane; acetone; toluene; pentane; 2.1: Willgerodt-Kindler oxidation;
DOI:10.1016/S0040-4020(00)01055-3

Reference yield:

: 122-46-3
3-acetoxytoluene

: 64052-99-9
rel-(3S,3aS,8bS)-7-bromo-3,6,8b-trimethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-3a-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1.1: 93 percent / ZrCl₄ / CH₂Cl₂ / 24 h / 20 °C / sonication

2.1: 97 percent / KOH / acetone / 15 h / 20 °C

3.1: 76 percent / S₈ / 24 h / 100 °C

4.1: 90 percent / H₂O / tetrahydrofuran / 18 h / Heating

5.1: 54 percent / t-BuLi / tetrahydrofuran; pentane / 9 h / -78 - 20 °C

6.1: 81 percent / BCl₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: 84 percent / N-isopropylcyclohexylamine; s-BuLi; HMPA / tetrahydrofuran; cyclohexane / 1.5 h / -78 - 20 °C

8.1: titanocene dichloride / heptane / 24 h / 20 °C

8.2: 54 percent / heptane; tetrahydrofuran / 20.5 h / -78 - 20 °C

9.1: 28 percent / Bu₃SnH; AIBN / toluene / 18 h / Heating

10.1: 52 percent / m-CPBA / CH₂Cl₂ / 24 h / 0 °C

11.1: 57 percent / Br₂; NaHCO₃ / CHCl₃ / 1 h / 0 °C

12.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With sulfur; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; 2,2'-azobis(isobutyronitrile); titanocene dichloride; N-cyclohexylisopropylamine; water; bromine; tert.-butyl lithium; sec.-butyllithium; tri-n-butyl-tin hydride; boron trichloride; zirconium(IV) chloride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; n-heptane; dichloromethane; chloroform; cyclohexane; acetone; toluene; pentane; 3.1: Willgerodt-Kindler oxidation;
DOI:10.1016/S0040-4020(00)01055-3