flustramine A

Base Information

• Chemical Name: flustramine A
• CAS No.: 71239-64-0
• Molecular Formula: C₂₁H₂₉BrN₂
• Molecular Weight: 389.379
• Mol file: 71239-64-0.mol

Synonyms:Pyrrolo[2,3-b]indole,6-bromo-3a-(1,1-dimethyl-2-propenyl)-1,2,3,3a,8,8a-hexahydro-1-methyl-8-(3-methyl-2-butenyl)-,(3aR,8aR)- (9CI); Pyrrolo[2,3-b]indole,6-bromo-3a-(1,1-dimethyl-2-propenyl)-1,2,3,3a,8,8a-hexahydro-1-methyl-8-(3-methyl-2-butenyl)-,(3aR-cis)-; (-)-Flustramine A; Flustramine A

Chemical Property of flustramine A

Chemical Property:

• Vapor Pressure: 6.95E-08mmHg at 25°C
• Boiling Point: 438.4°C at 760 mmHg
• Flash Point: 218.9°C
• PSA: 6.48000
• Density: 1.201g/cm³
• LogP: 5.34980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of flustramine A

There total 10 articles about flustramine A 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: 90.0%

(3aR,8aS)-6-bromo-1-methyl-8-(3-methylbut-2-enyl)-3a-(2-methylbut-3-en-2-yl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-2(1H)-one (82534-44-9) → Flustramine A (71239-64-0)

Guidance literature:

With Ν,Ν-dimethylethylamine alane; In tetrahydrofuran; toluene; at 20 ℃; for 0.0833333h;

DOI:10.1039/b512485a

Reference yield:

C17H36OSi (877797-53-0) → Flustramine A (71239-64-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

2.1: 4 Angstroem molecular sieves / acetonitrile; dimethylformamide / 144 h / 20 °C

3.1: t-BuOK / dimethylformamide / 1.5 h / 20 °C

3.2: 70 percent / dimethylformamide / -78 - 20 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: 97 percent / Ph₃P / CH₂Cl₂; methanol / -78 - 20 °C

5.1: 77 percent / NaH / dimethylformamide / 0.17 h / 0 °C

6.1: 83 percent / tetrahydrofuran / 1 h / 20 °C

7.1: 88 percent / aq. NaOH / methanol / 24 h / Heating

8.1: EDAC*HCl; C₆F₅OH; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

8.2: 76 percent / tetrahydrofuran / 20 °C

9.1: 92 percent / AlH₃*EtNMe₂ / tetrahydrofuran; toluene / 0.08 h / -15 °C

10.1: 90 percent / AlH₃*EtNMe₂ / tetrahydrofuran; toluene / 0.08 h / 20 °C

With sodium hydroxide; Ν,Ν-dimethylethylamine alane; 2,3,4,5,6-pentafluorophenol; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Wittig reaction;

DOI:10.1039/b512485a

Reference yield:

C21H28BrNO3 (877797-47-2) → Flustramine A (71239-64-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: t-BuOK / dimethylformamide / 1.5 h / 20 °C

1.2: 70 percent / dimethylformamide / -78 - 20 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 97 percent / Ph₃P / CH₂Cl₂; methanol / -78 - 20 °C

3.1: 77 percent / NaH / dimethylformamide / 0.17 h / 0 °C

4.1: 83 percent / tetrahydrofuran / 1 h / 20 °C

5.1: 88 percent / aq. NaOH / methanol / 24 h / Heating

6.1: EDAC*HCl; C₆F₅OH; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

6.2: 76 percent / tetrahydrofuran / 20 °C

7.1: 92 percent / AlH₃*EtNMe₂ / tetrahydrofuran; toluene / 0.08 h / -15 °C

8.1: 90 percent / AlH₃*EtNMe₂ / tetrahydrofuran; toluene / 0.08 h / 20 °C

With sodium hydroxide; Ν,Ν-dimethylethylamine alane; 2,3,4,5,6-pentafluorophenol; potassium tert-butylate; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction;

DOI:10.1039/b512485a

upstream raw materials:

(3aR,8aS)-6-bromo-1-methyl-8-(3-methylbut-2-enyl)-3a-(2-methylbut-3-en-2-yl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-2(1H)-one

C₁₇H₃₆OSi

C₂₁H₂₈BrNO₃

2-{(R)-6-bromo-3-[(E)-methyldec-3-en-2-yl]-2-oxoindolin-3-yl}acetonitrile

Refernces