2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-

Base Information

• Chemical Name: 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-
• CAS No.: 28656-91-9
• Deprecated CAS: 34140-52-8
• Molecular Formula: C9H9 Br2 N O3
• Molecular Weight: 338.983
• Hs Code.: 2941900000
• Nikkaji Number: J395.450A
• Wikidata: Q104935793
• Mol file: 28656-91-9.mol

Synonyms:NSC 170364;(1S-trans)-3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile;2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-;SMP2_000153;LS-56246;3,5-Dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1-acetonitrile

Chemical Property of 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-

Chemical Property:

• Vapor Pressure: 3.27E-11mmHg at 25°C
• Refractive Index: 1.645
• Boiling Point: 479.6°Cat760mmHg
• Flash Point: 243.8°C
• PSA: 73.48000
• Density: 2.01g/cm³
• LogP: 1.53738
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 338.89287
• Heavy Atom Count: 15
• Complexity: 382

Purity/Quality:

99.3% ^*data from raw suppliers

(+)shy-Aeroplysinin-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(C(C=C1Br)(CC#N)O)O)Br
• Description: (+)-Aeroplysinin-1 is a metabolite originally isolated from the marine sponge V. aerophoba with diverse biological activities. (+)-Aeroplysinin-1 (0.25-0.5 μM) induces cell death in MCF-7 and ZR-75-1 human breast cancer cells in a time- and concentration-dependent manner but has no effect on normal human fibroblasts at concentrations up to 5 μM. It also blocks EGF-induced endocytosis of the EGF receptor (EGFR) and EGF-dependent cell proliferation in MCF-7 cells. (+)-Aeroplysinin-1 inhibits bovine aortic endothelial (BAE) cell proliferation and cord formation in a Matrigel? assay. It inhibits angiogenesis in a dose-dependent manner in a chick chorioallantoic membrane (CAM) assay when administered from 1.5 to 3 nmol per egg. (+)-Aeroplysinin-1 also has antibacterial activity against Gram-positive bacteria, including S. aureus, S. albus, and B. subtilis, but not Gram-negative bacteria and inhibits HIV-1 replication (IC50 = 14.6 μM) via inhibition of HIV-1 reverse transcriptase.
• Uses: (+)shy-Aeroplysinin-1 is a compound that is an inhibitor of EGFR kinase.

Technology Process of 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)-

There total 7 articles about 2,4-Cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1S-trans)- 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: 94.0%

(5S,10R)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate (179798-47-1) → Aeroplysinin I (28656-91-9)

Guidance literature:

With sodium hydroxide; Heating;

DOI:10.1016/j.tetlet.2005.11.097

Reference yield:

(+)-aerophobin 2 → Aeroplysinin I (28656-91-9)

Guidance literature:

With 1H-imidazole; marine sponge Aplysina aerophoba; In ethanol; at 50 ℃; for 0.333333h; pH=6.8; Enzymatic reaction;

DOI:10.1023/B:JOEC.0000006475.10310.3a

Reference yield:

Aplysinamisin-1 → Aeroplysinin I (28656-91-9)

Guidance literature:

With 1H-imidazole; marine sponge Aplysina aerophoba; In ethanol; at 50 ℃; for 0.333333h; pH=6.8; Enzymatic reaction;

DOI:10.1023/B:JOEC.0000006475.10310.3a

upstream raw materials:

(5S,10R)-methyl 7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxylate

(5S,10R)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester

(5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate

Downstream raw materials:

2,6-dibromo-4-hydroxy-4-carbamoylmethylcyclohexa-2,5-dien-1-one

C₁₀H₁₁Br₂NO₃

(1′R,5′S,6′S)-2-(3′,5′-dibromo-1′,6′-dihydroxy-4′-oxocyclohex-2′-enyl)acetonitrile

C₈H₇Br₂NO₃