Dihydroretrofractamide B

Base Information

Chemical Name:Dihydroretrofractamide B
CAS No.:75022-26-3
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:
DSSTox Substance ID:DTXSID601149493
Nikkaji Number:J1.010.288J
Wikidata:Q76416158
Metabolomics Workbench ID:45705

$Dihydroretrofractamide B$

Synonyms:Dihydroretrofractamide B;Dihydrop ipercide;10,11-Dihydropipercide;SCHEMBL11305653;SCHEMBL11307682;CHEBI:174786;DTXSID601149493;(2E,4E)-11-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2,4-undecadienamide;(2E,4E)-11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienamide;(2E,4E)-11-(2H-1,3-BENZODIOXOL-5-YL)-N-(2-METHYLPROPYL)UNDECA-2,4-DIENAMIDE;75022-26-3

Suppliers and Price of Dihydroretrofractamide B

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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Total 0 raw suppliers

Chemical Property of Dihydroretrofractamide B

Chemical Property:

XLogP3:6.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:11
Exact Mass:357.23039385
Heavy Atom Count:26
Complexity:458

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)CNC(=O)C=CC=CCCCCCCC1=CC2=C(C=C1)OCO2
Isomeric SMILES:CC(C)CNC(=O)/C=C/C=C/CCCCCCC1=CC2=C(C=C1)OCO2

Technology Process of Dihydroretrofractamide B

There total 23 articles about Dihydroretrofractamide B 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%

: 78-81-9
isobutylamine

: 214462-90-5
(2E,4E)-11-Benzo[1,3]dioxol-5-yl-undeca-2,4-dienoyl chloride

$10,11-dihydroretrofractamide B$: 75022-26-3
10,11-dihydroretrofractamide B

Guidance literature:: With triethylamine; In diethyl ether; at 0 - 20 ℃;
DOI:10.1021/jo981039d

Reference yield: 68.2%

: 78-81-9
isobutylamine

: 75069-53-3
11-(3',4'-methylenedioxyphenyl)-undeca-2(E),4(E)-dienoic acid

$10,11-dihydroretrofractamide B$: 75022-26-3
10,11-dihydroretrofractamide B

Guidance literature:: With triethylamine; In dichloromethane; 1) 0 deg C, 1 h, 2) room temperature, 30 min;

Reference yield:

: 2606-51-1
3,4-Methylenedioxybenzyl bromide

$10,11-dihydroretrofractamide B$: 75022-26-3
10,11-dihydroretrofractamide B

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / dimethylformamide / 1.5 h / 60 °C

2: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C

3: 99 percent / H₂ / Pd/C / methanol / 3 h / 1913.4 Torr

4: 96 percent / LiAlH₄ / tetrahydrofuran / 1 h / 21 - 29 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl_2. -65 deg C, 4 h, 2.) CH₂Cl₂, -65 deg C to -10 deg C, overnight

6: 1.) LDA / 1.) THF, hexane, -23 deg C, 5 min, 2.) THF, hexane, -23 deg C, 2 h

7: 98 percent / KOH / ethanol; H₂O / Ambient temperature

8: (COCl)2 / benzene / 2 h / Heating

9: 90 percent / Et₃N / diethyl ether / 0 - 20 °C

With potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo981039d