CID 6451060

Base Information

• Chemical Name: CID 6451060
• CAS No.: 3484-37-5
• Molecular Formula: C20H24O4
• Molecular Weight: 328.4
• Wikidata: Q105146012
• Metabolomics Workbench ID: 137321
• ChEMBL ID: CHEMBL470287
• Mol file: 3484-37-5.mol

Synonyms:ovatodiolide

Chemical Property of CID 6451060

Chemical Property:

• Vapor Pressure: 4E-13mmHg at 25°C
• Boiling Point: 572.7°C at 760 mmHg
• Flash Point: 299.1°C
• PSA: 52.60000
• Density: 1.15g/cm³
• LogP: 3.79270
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 665

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC2=CC(CC(=CC3C(CC1)C(=C)C(=O)O3)C)OC2=O
• Isomeric SMILES: C/C/1=C\CCC2=C[C@@H](C/C(=C/[C@H]3[C@H](CC1)C(=C)C(=O)O3)/C)OC2=O

Technology Process of CID 6451060

There total 14 articles about CID 6451060 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:

C22H28O4 → C20H24O4 + ovatodiolide (3484-37-5,63700-26-5)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 120 ℃; for 3h; Reagent/catalyst; Overall yield = 60 percent; Overall yield = 1.10 g; Inert atmosphere;

DOI:10.1002/anie.201904096

Reference yield:

(Z)-6-methyl-2-((4,4,5,5-tetramethyl- 1,3,2-Dioxaborolan-2-yl)methyl)hepta-2,6-dienoic acid methyl ester → C20H24O4 + ovatodiolide (3484-37-5,63700-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: C₄₄H₅₃O₄P / toluene / 168 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.75 h / -78 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / toluene / 3 h / 120 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; C₄₄H₅₃O₄P; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1002/anie.201904096

Reference yield:

C9H12O2 → C20H24O4 + ovatodiolide (3484-37-5,63700-26-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide / toluene / 8 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: C₄₄H₅₃O₄P / toluene / 168 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.75 h / -78 °C / Inert atmosphere

4.1: Hoveyda-Grubbs catalyst second generation / toluene / 3 h / 120 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; Hoveyda-Grubbs catalyst second generation; C₄₄H₅₃O₄P; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1002/anie.201904096

upstream raw materials:

1-methoxy-3-methyl-1-trimethylsilyloxy-1,3-butadiene

(Z)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

Refernces

• 1、 Xiang, Junhong,Ding, Yahui,Li, Jiaxin,Zhao, Xiuhe,Sun, Yuanjun,Wang, Da,Wang, Liang,Chen, Yue. "Ovatodiolides: Scalable Protection-Free Syntheses, Configuration Determination, and Biological Evaluation against Hepatic Cancer Stem Cells". . p. 10587 - 10590. Retrieved 2019/07/04.