(3Z)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-(5-methyl-6-oxopyran-2-yl)hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione

Base Information

• Chemical Name: (3Z)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-(5-methyl-6-oxopyran-2-yl)hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione
• CAS No.: 160796-24-7
• Molecular Formula: C₃₀H₃₈O₄
• Molecular Weight: 462.629
• Mol file: 160796-24-7.mol

Synonyms:stellettin A

Chemical Property of (3Z)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-(5-methyl-6-oxopyran-2-yl)hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione

Chemical Property:

• Vapor Pressure: 2.56E-15mmHg at 25°C
• Boiling Point: 620.4°C at 760 mmHg
• Flash Point: 262.2°C
• PSA: 64.35000
• Density: 1.107g/cm³
• LogP: 6.62490
• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 462.27700969
• Heavy Atom Count: 34
• Complexity: 1110

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(OC1=O)C(=CC=CC(=C2C(=O)CC3C2(CCC4C3(CCC(=O)C4(C)C)C)C)C)C
• Isomeric SMILES: CC1=CC=C(OC1=O)/C(=C/C=C/C(=C/2\C(=O)CC3C2(CCC4C3(CCC(=O)C4(C)C)C)C)/C)/C

Technology Process of (3Z)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-(5-methyl-6-oxopyran-2-yl)hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione

There total 29 articles about (3Z)-3a,6,6,9a-tetramethyl-3-[(3E,5E)-6-(5-methyl-6-oxopyran-2-yl)hepta-3,5-dien-2-ylidene]-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalene-2,7-dione 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: 64.0%

C19H27BrO2 + 3-methyl-6-((2E,4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dien-2-yl)-2H-pyran-2-one → (-)-iso-stelletin A + (+)-stelletin A (160796-24-7)

Guidance literature:

With potassium trimethylsilonate; palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; at 55 ℃; Reagent/catalyst; Solvent; Inert atmosphere; Darkness; Glovebox; Sealed tube;

DOI:10.1021/jacs.0c12569 DOI:10.1021/jacs.1c07261

Reference yield:

C19H27BrO2 + 3-methyl-6-((2E,4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dien-2-yl)-2H-pyran-2-one → (±)-9-epi-stelletin A (160796-24-7)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium carbonate; In tetrahydrofuran; water; at 20 - 65 ℃; for 6h; Sonication; Inert atmosphere; Darkness;

DOI:10.1021/jacs.0c12569 DOI:10.1021/jacs.1c07261

Reference yield:

C19H27BrO2 + 3-methyl-6-((2E,4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dien-2-yl)-2H-pyran-2-one → (-)-9-epi-stelletin A (160796-24-7)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium carbonate; In tetrahydrofuran; water; at 20 - 65 ℃; for 6h; Sonication; Inert atmosphere; Darkness;

DOI:10.1021/jacs.0c12569 DOI:10.1021/jacs.1c07261

upstream raw materials:

(4aR,6S,8aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

(E)-3-(3-methyl-2-oxo-2H-pyran-6-yl)but-2-enal

Refernces

• 1、 Boyko, Yaroslav D.,Chu, Tiffany,Hergenrother, Paul J.,Huck, Christopher J.,Ning, Shang,Sarlah, David,Shved, Alexander S.,Tonogai, Emily J.,Yang, Cheng. "Erratum: Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques (J. Am. Chem. Soc. (2021) 143:4 (2138-2155) DOI: 10.1021/jacs.0c12569)". supporting information. p. 12418 - 12418. Retrieved 2021/08/30.