[(2Z)-12-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (E)-2-methylbut-2-enoate

Base Information

• Chemical Name: [(2Z)-12-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (E)-2-methylbut-2-enoate
• CAS No.: 78657-58-6
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423
• NSC Number: 329694,329691
• ChEMBL ID: CHEMBL1989874
• Mol file: 78657-58-6.mol

Synonyms:NSC329694;HM-4;HM-8;NSC329691;CHEMBL1989874;78657-58-6;NSC-329691;NSC-329694

Chemical Property of [(2Z)-12-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (E)-2-methylbut-2-enoate

Chemical Property:

• Vapor Pressure: 1.09E-13mmHg at 25°C
• Boiling Point: 535.2°Cat760mmHg
• Flash Point: 187.1°C
• Density: 1.22g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 362.17293854
• Heavy Atom Count: 26
• Complexity: 705

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC1CC2(C(CC(O2)C(=CC3C1C(=C)C(=O)O3)C)O)C
• Isomeric SMILES: C/C=C(\C)/C(=O)OC1CC2(C(CC(O2)/C(=C\C3C1C(=C)C(=O)O3)/C)O)C

Technology Process of [(2Z)-12-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (E)-2-methylbut-2-enoate

There total 4 articles about [(2Z)-12-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (E)-2-methylbut-2-enoate 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: 50.0%

(-)-(1R,10R)-1,10-epoxynobilin → (+)-(4Z,1R,3R,6R,7R,8S,10S)-8-angeloxy-3,10-epoxy-1-hydroxy-germacra-4(5),11(13)-dien-6,12-olide (78657-58-6)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; at 20 ℃; Cooling with ice;

DOI:10.3390/molecules22122252

Reference yield: 50.0%

(-)-(1R,10R)-1,10-epoxynobilin → (+)-(4Z,1R,3R,6R,7R,8S,10S)-8-angeloxy-3,10-epoxy-1-hydroxy-germacra-4(5),11(13)-dien-6,12-olide (78657-58-6) + C20H26O6

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃;

DOI:10.3390/molecules22122252

Reference yield:

nobilin → (+)-(4Z,1R,3R,6R,7R,8S,10S)-8-angeloxy-3,10-epoxy-1-hydroxy-germacra-4(5),11(13)-dien-6,12-olide (78657-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C / Cooling with ice

2: boron trifluoride diethyl etherate / toluene / 20 °C / Cooling with ice

With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

DOI:10.3390/molecules22122252

Downstream raw materials:

(Z)-2-Methyl-but-2-enoic acid (Z)-(1R,4S,9R,11R,12S)-1,12-dihydroxy-2,11-dimethyl-7-methylene-6-oxo-5,14-dioxa-tricyclo[9.2.1.0^4,8]tetradec-2-en-9-yl ester