Ecklonialactone B

Base Information

• Chemical Name: Ecklonialactone B
• CAS No.: 121923-96-4
• Molecular Formula: C₁₈H₂₈O₃
• Molecular Weight: 292.419
• Wikidata: Q105151310
• Mol file: 121923-96-4.mol

Synonyms:ecklonialactone B

Chemical Property of Ecklonialactone B

Chemical Property:

• Vapor Pressure: 3.74E-08mmHg at 25°C
• Boiling Point: 446.1°Cat760mmHg
• Flash Point: 190.9°C
• PSA: 38.83000
• Density: 1.005g/cm³
• LogP: 4.01220
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 292.20384475
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C2CC3C(C2C=CCCCCCCCC(=O)O1)O3
• Isomeric SMILES: CCC1C2C[C@H]3C(C2/C=C/CCCCCCCC(=O)O1)O3

Technology Process of Ecklonialactone B

There total 88 articles about Ecklonialactone 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%

C18H26O3 (1239709-02-4) → (-)-ecklonialactone B (121923-96-4)

Guidance literature:

With hydrogen; In dichloromethane; at 20 ℃; for 2.5h; under 760.051 Torr;

DOI:10.1021/ja104796a

Reference yield: 83.0%

C18H28O2 (1485377-99-8) → 12,13-epi-ecklonialactone B (1239708-99-6,121923-96-4)

Guidance literature:

With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 3h; diastereoselective reaction;

DOI:10.1021/ol4028418

Reference yield: 80.0%

C18H26O3 (1239708-98-5) → 12,13-epi-ecklonialactone B (1239708-99-6,121923-96-4)

Guidance literature:

With hydrogen; In dichloromethane; at 20 ℃; for 2.5h; under 760.051 Torr;

DOI:10.1021/ja104796a

upstream raw materials:

C₁₈H₂₆O₃

C₉H₁₅NO₃

C₉H₁₃NO₃

C₁₀H₁₃NO₂

Refernces

Total synthesis of (-)-ecklonialactone B

10.1021/ol4028418

The study reports the total synthesis of (?)-ecklonialactone B and its 9,10-dihydro derivative using two different strategies. Key chemicals involved include Gosteli-type allyl vinyl ethers, which serve as starting materials for the catalytic asymmetric Claisen rearrangement to produce R-keto ester building blocks. These esters are crucial intermediates that undergo further transformations such as K-Selectride reduction, reductive homologation, and ring-closing metathesis (RCM) to form the cyclopentenoid building blocks. The synthesis also involves a B-alkyl Suzuki–Miyaura cross-coupling reaction and a final regio- and diastereoselective epoxidation to achieve the target compounds. The study explores various catalysts and conditions for these reactions, such as the Grubbs catalyst for RCM and the Hoveyda–Grubbs catalyst for diastereotopos-differentiating RCM, to optimize yields and selectivity. The research demonstrates a strategic approach to synthesizing complex natural products with high stereocontrol and functional group transformations.

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