(1R,2R,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Base Information

• Chemical Name: (1R,2R,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
• CAS No.: 84573-16-0
• Molecular Formula: C₂₉H₃₁NO₇
• Molecular Weight: 505.568
• Mol file: 84573-16-0.mol

Synonyms:rocaglamide;rocaglamide A

Chemical Property of (1R,2R,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Chemical Property:

• Vapor Pressure: 1.02E-18mmHg at 25°C
• Melting Point: 117-118 °C
• Boiling Point: 667.3°C at 760 mmHg
• PKA: 11.70±0.70(Predicted)
• Flash Point: 357.4°C
• PSA: 97.69000
• Density: 1.321g/cm³
• LogP: 3.05060
• Storage Temp.: ?20°C
• Solubility.: Soluble in DMSO or Ethanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 505.21005233
• Heavy Atom Count: 37
• Complexity: 810

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rocaglamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)C1C(C2(C(C1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5
• Isomeric SMILES: CN(C)C(=O)[C@H]1[C@H]([C@]2(C3=C(C=C(C=C3OC)OC)O[C@]2(C1C4=CC=CC=C4)C5=CC=C(C=C5)OC)O)O
• Description: Rocaglamide is an anti-inflammatory, insecticidal, and anticancer tetrahydrobenzofuran isolated from Aglaia species. It has been shown to inhibit both TNF-α and the activation of NF-κB in Jurkat T cells with IC50 values in the nanomolar range. At 25 nM, rocaglamide induces apoptosis in various human leukemia cell lines, activating p38 MAPK/JNK and suppressing ERK. Rocaglamide also reduces IFN-γ, TNF-α, IL-2, and IL-4 production in peripheral blood T cells at a concentration of 50 nM. Furthermore, rocaglamide can inhibit the T cell expression of the immune response transcription factor, nuclear factor of activated T cells.
• Uses: Rocaglamide is derived from a Chinese medicinal plant Aglaia. Rocaglamide induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells freshly isolated from patients.

Technology Process of (1R,2R,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

There total 68 articles about (1R,2R,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide 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: 73.0%

(2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide (1139257-91-2) → rocaglamide (84573-16-0,117894-34-5,134931-37-6,145679-29-4)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In acetonitrile; at 20 ℃; for 20h;

DOI:10.1002/anie.201501374

Reference yield: 65.0%

N,N-dimethylammonium chloride (506-59-2) + endo rocaglic acid (190385-15-0) → rocaglamide (84573-16-0,117894-34-5,134931-37-6,145679-29-4)

Guidance literature:

N,N-dimethylammonium chloride; endo rocaglic acid; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.583333h;

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 13h;

With hydrogenchloride; In water; N,N-dimethyl-formamide;

Reference yield: 24.0%

dimethyl amine (124-40-3) + endo rocaglic acid (190385-15-0) → rocaglamide (84573-16-0,117894-34-5,134931-37-6,145679-29-4)

Guidance literature:

With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1021/np970163+

upstream raw materials:

(2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide

dimethyl amine

endo rocaglic acid

N,N-dimethylammonium chloride

Refernces

• 1、 Zhou, Zhe,Tius, Marcus A.. "Synthesis of each enantiomer of rocaglamide by means of a palladium(0)-catalyzed nazarov-type cyclization". supporting information. p. 6037 - 6040. Retrieved 2015/05/13.
• 2、 Malona, John A.,Cariou, Kevin,Frontier, Alison J.. "Nazarov cyclization initiated by peracid oxidation: The total synthesis of (±)-rocaglamide". supporting information; experimental part. p. 7560 - 7561. Retrieved 2009/10/17.