Periplanone B

Base Information

• Chemical Name: Periplanone B
• CAS No.: 61228-92-0
• Molecular Formula: C15H20 O3
• Molecular Weight: 248.322
• UNII: 8HV41M9E86,GW5DRN3VEK
• DSSTox Substance ID: DTXSID4058441
• Nikkaji Number: J410.741A
• Wikipedia: Periplanone_B
• Wikidata: Q2594205
• Metabolomics Workbench ID: 143704
• Mol file: 61228-92-0.mol

Synonyms:Periplanone B;(-)-Periplanone B;61228-92-0;(+/-)-Periplanone B;Periplanone B, (+/-)-;(+/-)-Periplanone B [MI];GW5DRN3VEK;UNII-GW5DRN3VEK;Caswell No. 333F;UNII-8HV41M9E86;8HV41M9E86;EPA Pesticide Chemical Code 124801;70613-99-9;Spiro(11-oxabicyclo(8.1.0)undec-6-ene-2,2'-oxiran)-3-one, 8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-;Spiro(11-oxabicyclo(8.1.0)undec-6-ene-2,2'-oxiran)-3-one, 8-methylene-5-(1-methylethyl)-, (1R,2R,5S,6E,10R)-rel-;(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one;Lure & Kill Roach & Ant Killer with Sex Lure;Periplanone-B;Periplanon B;Spiro(11-oxabicyclo(8.1.0)undec-6-ene-2,2'-oxiran)-3-one, 8-methylene-5-(1-methylethyl)-, (1R-(1R*,2R*,5S*,6E,10R*))-;Spiro(11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran)-3-one, 8-methylene-5-(1-methylethyl)-, [1R-(1R*,2R*,5S*,6E,10R*)]-;1,10(14)-Diepoxy-4(15),5-germecradiene-9-one;PERIPLANONE B [MI];SCHEMBL421949;DTXSID4058441;Q2594205;(1R,2R,5S,6E,10R)-8-methylidene-5-propan-2-ylspiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxirane]-3-one

Chemical Property of Periplanone B

Chemical Property:

• Melting Point: 47-50°
• PSA: 42.13000
• LogP: 2.27030
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 424

Purity/Quality:

99%, ^*data from raw suppliers

PERIPLANONE B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CC(=O)C2(CO2)C3C(O3)CC(=C)C=C1
• Isomeric SMILES: CC(C)[C@@H]\1CC(=O)[C@@]2(CO2)[C@H]3[C@H](O3)CC(=C)/C=C1

Technology Process of Periplanone B

There total 74 articles about Periplanone 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: 92.0%

(1S,3S,4E,8R,9R,10S)-8,9-epoxy-10,10-epoxymethano-3-isopropyl-6-methylene-4-cyclodecen-1-ol (70800-65-6,70831-70-8,70831-72-0,70831-75-3,84236-08-8) → (3S,8R,9R,10S)-(-)-periplanone-B (61228-92-0)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81464-2

Reference yield:

(4S,5E,9R,10R)-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one (105930-39-0) → (3S,8R,9R,10S)-(-)-periplanone-B (61228-92-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / LiN(TMS)2, MoO₅*HMPA*Py / tetrahydrofuran

2: imidazole / dimethylformamide

3: n-BuLi / tetrahydrofuran

4: n-Bu₄NF / tetrahydrofuran

5: 92 percent / PDC / dimethylformamide

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

(2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one (113666-35-6) → (3S,8R,9R,10S)-(-)-periplanone-B (61228-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran

2: n-Bu₄NF / tetrahydrofuran

3: 92 percent / PDC / dimethylformamide

With dipyridinium dichromate; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

Periplanol B

(5S,6R)-6-((E)-3-Methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enone

(1S,5S,6R)-6-((E)-3-Methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-1-vinyl-cyclohex-2-enol

(1R,2S,6S)-6-(Tetrahydro-pyran-2-yloxymethyl)-2-trimethylsilanyloxy-cyclohex-3-enecarbaldehyde

Refernces

• 1、 Kuwahara, Shigefumi,Mori, Kenji. "A new stereoselective synthesis of (-)-periplanone-B". . p. 167 - 170. Retrieved 2007/10/02.
• 2、 Hauptmann, H.,Muehlbauer, G.. "SYNTHESE UND KRISTALLSTRUKTUR VON (+/-)-PERIPLANON B". . p. 1315 - 1318. Retrieved 2007/10/02.