Rugulovasine B

Base Information

• Chemical Name: Rugulovasine B
• CAS No.: 26909-34-2
• Molecular Formula: C₁₆H₁₆N₂O₂
• Molecular Weight: 268.315
• UNII: 0E5879R1WV
• DSSTox Substance ID: DTXSID901046325
• Nikkaji Number: J657.906J
• Wikidata: Q27236662
• Metabolomics Workbench ID: 161519
• Mol file: 26909-34-2.mol

Synonyms:rugulovasine B;rugulovasine B hydrochloride, (trans-(+-))-isomer

Chemical Property of Rugulovasine B

Chemical Property:

• Boiling Point: 550.3°Cat760mmHg
• Flash Point: 286.6°C
• PSA: 54.12000
• Density: 1.32g/cm³
• LogP: 2.40130
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 268.121177757
• Heavy Atom Count: 20
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2(C(CC3=CNC4=CC=CC2=C34)NC)OC1=O
• Isomeric SMILES: CC1=C[C@@]2([C@@H](CC3=CNC4=CC=CC2=C34)NC)OC1=O
• Description: From cultures of Penicillium concavorugulosum, this isomer of the preceding alkaloid has been obtained. It also forms an amorphous solid which cannot be crystallized and has [α]22436 + lAO (c 1.0, pyridine). It furnishes the corresponding dihydro derivative with m.p. 222-5°C (dec.).

Technology Process of Rugulovasine B

There total 11 articles about Rugulovasine 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:

4-(N-benzyloxycarbonyl-N-methylamino)-3,4-dihydro4'-methyl-1-[(1,1-dimethylethyloxy)carbonyl]-spiro[benz[cd]indole-5(1H),2'-[(5'H)-furan-5'-one]] → 4'-methyl-4c-methylamino-3,4-dihydro-1H-(5rO)-spiro[benzo[cd]indole-5,2'-furan]-5'-one (607363-43-9) + rugulovasine B (26909-34-2) + rugulovasine A (26909-33-1)

Guidance literature:

4-(N-benzyloxycarbonyl-N-methylamino)-3,4-dihydro4'-methyl-1-[(1,1-dimethylethyloxy)carbonyl]-spiro[benz[cd]indole-5(1H),2'-[(5'H)-furan-5'-one]]; With caesium carbonate; In tetrahydrofuran; methanol; at 20 ℃; for 36h;

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; at 20 ℃; for 0.166667h; under 760.051 Torr; Further stages.;

DOI:10.1021/ja010577w

Reference yield:

C23H22N2O2*ClH → rugulovasine B (26909-34-2) + rugulovasine A (26909-33-1)

Guidance literature:

With hydrogenchloride; hydrogen; 20percent Pd(OH)2; In ethanol; at 20 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ja010577w

Reference yield:

1,3,4,5-tetrahydro-5-hydroxy-α-methyl-4-(methylbenzamido)benzindole-5-acrylic acid γ-lactone (74644-92-1) → rugulovasine B (26909-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) t-BuOK, NaOH / 1.) THF, 2.) DMSO, 80 deg C, 4 h

2: methanol / 48 h / Ambient temperature

With sodium hydroxide; potassium tert-butylate; In methanol;

DOI:10.1021/ja00536a067

upstream raw materials:

rugulovasine A

rugulovasine A

2-benzoylamino-3-(1-benzoyl-2,3-dihydro-indol-3-yl)-propionic acid

1,3,4,5-tetrahydro-5-hydroxy-α-methyl-4-(methylbenzamido)benzindole-5-acrylic acid γ-lactone

Downstream raw materials:

rugulovasine A