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

Base Information

• Chemical Name: Methyl cis-10,11-epoxy-3,11-dimethyl-7-ethyl-trans,trans-2,6-tridecadienoate
• CAS No.: 13804-51-8
• Deprecated CAS: 24193-20-2,17447-05-1,23334-69-2,33212-32-7,106974-33-8
• Molecular Formula: C18H30 O3
• Molecular Weight: 294.434
• Hs Code.: 2918990090
• UNII: 3Q8213U4LQ
• DSSTox Substance ID: DTXSID201024926
• Nikkaji Number: J37.974C,J2.915.671I
• Wikidata: Q27105096
• Mol file: 13804-51-8.mol

Synonyms:C18-juvenile hormone;juvenile hormone I;juvenile hormone I, (2alpha(2E,6E),3alpha)-(+-)-isomer;juvenile hormone I, (2alpha(2E,6E),3beta)-(+-)-isomer;juvenile hormone I, (2alpha(2E,6E),3beta)-isomer;juvenile hormone I, (2alpha(2E,6Z),3beta)-(+-)-isomer;juvenile hormone I, (2alpha(2Z,6E),3alpha)-(+-)-isomer;juvenile hormone I, (2alpha(2Z,6E),3beta)-(+-)-isomer;juvenile hormone I, (2alpha(2Z,6Z),3alpha)-(+-)-isomer;juvenile hormone I, (2alpha(2Z,6Z),3beta)-(+-)-isomer;juvenile hormone I, (2R-(2alpha(2E,6E),3alpha))-isomer;juvenile hormone-I;methyl-7-ethyl-3,11-dimethyl-cis-10,11-oxido-trans,trans-2,6-tridecadienoate

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

Chemical Property:

• Vapor Pressure: 5.94E-06mmHg at 25°C
• Refractive Index: nD24 1.4732
• Boiling Point: 379.2°C at 760 mmHg
• Flash Point: 159.3°C
• PSA: 38.83000
• Density: 0.95g/cm³
• LogP: 4.57000
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• 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

JuvenileHormoneI ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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)/CC[C@@H]1[C@](O1)(C)CC
• Uses: Juvenile Hormone I is an acyclic sesquiterpenoid that regulates many aspects of insect physiology. Juvenile Hormone regulate development, reproduction, diapause, and polyphenisms.

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

There total 46 articles about Methyl cis-10,11-epoxy-3,11-dimethyl-7-ethyl-trans,trans-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:

butanone

(-)-juvenile hormone I

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

Refernces

• 1、 Stotter,Hornish. "-". . p. 4444,4445. Retrieved 1973.
• 2、 Johnson,W.S. et al.. "". . p. 4463 - 4464. Retrieved 1970.
• 3、 Okochi,Mori. "New enantioselective synthesis of (10R, 11S)-(+)-juvenile hormones I and II". . p. 2145 - 2150. Retrieved 2007/10/03.
• 4、 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.