Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate

Base Information

• Chemical Name: Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate
• CAS No.: 23314-84-3
• Deprecated CAS: 25525-62-6,25525-63-7,21161-55-7,50641-91-3,29751-36-8
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.434
• Nikkaji Number: J1.037.358A
• Mol file: 23314-84-3.mol

Synonyms:Roeller compound;JH 1;23314-84-3;Ro 6-9550;AY 22342;AI3-33972;methyl (2E,6E)-7-ethyl-9-(3-ethyl-3-methyloxiran-2-yl)-3-methylnona-2,6-dienoate;Methyl-12-homojuvenate;12,14-Dihomojuvenate;Methyl 10,11-epoxy-1,11-dimethyl-7-ethyl-2,6-tridecadienoate;Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate;Methyl 10,11-epoxy-7-ethyl-3,11-dimethy,-2,6-tridecadienoate;Methyl 3,11-dimethyl-10,11-epoxy-7-ethyl-2,6-diene-tridecanoate;Methyl 3,11-dimethyl-10-epoxy-7-ethyl-trans,trans-2,6-tridecadienoate;2,6-Tridecadienoic acid, 10,11-epoxy-7-ethyl-3,11-dimethyl-, methyl ester;3,11-Dimethyl-10,11-epoxy-7-ethyl-2,6-tridecadienoic acid methyl ester;2,6-Nonadienoic acid, 7-ethyl-9-(3-ethyl-3-methyloxiranyl)-3-methyl-, methyl ester;7-Ethyl-9-(3-ethyl-3-methyloxiranyl)-1-methyl-2,6-nonadienoic acid methyl ester;7-Ethyl-9-(3-ethyl-3-methyloxiranyl)-3-methyl-2,6-nonadienoic acid methyl ester;2,6-Tridecadienoic acid, 3,11-dimethyl-10,11-epoxy-7-ethyl-, methyl ester;2,6-Tridecadienoic acid, 3,11-dimethyl-10,11-epoxy-7-ethyl-, methyl ester, (E,E)-cis-;AY 22243;AI 3-33972;10,11-Epoxy-7-ethyl-3,11-dimethyltrideca-2-cis-6-dienoic acid, methyl ester;cis/trans-methyl 10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate;Methyl 10,11-epoxy-7-ethyl-3,11-dimethyl-trans,trans,cis-2,6-tridecadienoate;Methyl cis-10,11-epoxy-7-ethyl-3,11-dimethyl-trans,trans-2,6-tridecadienoate;Methyl trans,trans,cis-10,11-epoxy-7-ethyl-3,11-dimethyltrideca-2,6-dienoate;SCHEMBL7709823;SCHEMBL8767062;2,6-Tridecadienoic acid, 10,11-epoxy-7-ethyl-3,11-dimethyl-, methyl ester, (E,E)-cis-;RQIDGZHMTWSMMC-SKDLNQQGSA-N;2,6-Nonadienoic acid, 7-ethyl-9-(3-ethyl-3-methyloxiranyl)-3-methyl-, methyl ester, (2R-(2alpha(2E,6E),3alpha))-;2,6-Nonadienoic acid, 7-ethyl-9-(3-ethyl-3-methyloxiranyl)-3-methyl-, methyl ester, [2R-[2.alpha.(2E,6E),3.alpha.]]-;LS-157136;LS-157137;methyl 10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate;(2E,6E)-10,11-Epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoic acid methyl ester;Methyl (2E,6E)-7-ethyl-9-(3-ethyl-3-methyl-2-oxiranyl)-3-methyl-2,6-nonadienoate #

Chemical Property of Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate

Chemical Property:

• Boiling Point: 379.2°Cat760mmHg
• Flash Point: 159.3°C
• Density: 0.95g/cm³
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Safety Statements: Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.:

MSDS Files:

Useful:

• Canonical SMILES: CCC(=CCCC(=CC(=O)OC)C)CCC1C(O1)(C)CC
• Isomeric SMILES: CC/C(=C\CC/C(=C/C(=O)OC)/C)/CCC1C(O1)(C)CC

Technology Process of Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate

There total 45 articles about Methyl 3,11-dimethyl-7-ethyl-10,11-epoxy-2,6-tridecadienoate 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: 79.0%

(2E,6E)-(10S,11S)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester (119615-14-4) → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)85826-9

Reference yield: 79.0%

C24H34O6S (1389395-08-7) + dimethyl zinc(II) (544-97-8) → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1055/s-0031-1290803

Reference yield:

(2E,6E)-(10S,11R)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1002/1099-0690(200106)2001:11<2145::AID-EJOC2145>3.0.CO;2-J

upstream raw materials:

(2E,6E)-(10S,11S)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester

(2E,6E)-7-Ethyl-9-((2R,3S)-3-ethyl-3-methyl-oxiranyl)-3-methyl-nona-2,6-dienoic acid methyl ester

methyl (2E,6E,10E)-7-ethyl-3,11-dimethyltrideca-2,6,10-trienone

(3E)-1-iodo-4-methylhex-3-ene

Downstream raw materials:

(-)-juvenile hormone I

methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate

Refernces

• 1、 Okochi,Mori. "New enantioselective synthesis of (10R, 11S)-(+)-juvenile hormones I and II". . p. 2145 - 2150. Retrieved 2007/10/03.
• 2、 Peter, Martin G.,Stupp, Hans-Peter,Lentes, Klaus-Ulrich. "Umkehr der Enantioselektivitaet bei der enzymatischen Hydrolyse von Juvenilhormon als Ergebnis einer Proteinfraktionierung". . p. 794 - 795. Retrieved 2007/10/02.