Sordidin

Base Information

• Chemical Name: Sordidin
• CAS No.: 162490-88-2
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.279
• European Community (EC) Number: 805-494-9
• Nikkaji Number: J734.589E
• Wikidata: Q104375915
• Mol file: 162490-88-2.mol

Synonyms:2,8-dioxa-1-ethyl-3,5,7-trimethylbicyclo(3.2.1)octane;sordidin

Chemical Property of Sordidin

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

99%, ^*data from raw suppliers

(1S,3R,5R,7S)Sordidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12C(CC(O1)(CC(O2)C)C)C
• Isomeric SMILES: CC[C@@]12[C@H](C[C@@](O1)(C[C@H](O2)C)C)C
• Uses: (1S,3R,5R,7S) Sordidin is an aggregation pheromone of the banana weevil which is an insect pest of bananas. Used in conjunction with pesticides for pest removal.

Technology Process of Sordidin

There total 140 articles about Sordidin 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%

C13H26O4 (1131229-59-8) → (1R,3R,5S,7R/S)-sordidin (162490-88-2)

Guidance literature:

With oxalic acid; In water; pentane; at 20 ℃;

DOI:10.1055/s-0028-1087373

Reference yield: 75.0%

C13H26O4 (1131229-48-5) → (1S,3R,5R,7S)-(+)-sordinin (162490-88-2)

Guidance literature:

With water; oxalic acid; In pentane; at 20 ℃;

DOI:10.1055/s-0028-1087373

Reference yield: 62.0%

(S)-2-methyl-1-((4R,6R)-2,2,4,6-tetramethyl-1,3-dioxan-4-yl)pentan-3-one (1013652-10-2) → (1S,3R,5R,7S)-(+)-sordinin (162490-88-2)

Guidance literature:

With oxalic acid; In pentane; at 0 ℃; for 48h;

DOI:10.1016/j.tet.2007.12.051

upstream raw materials:

ethyllithium

3-pentanone N,N-dimethylhydrazone

N-Cyclohexyldiethylketimine

2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-propyl]-pentane-1,4-diol

Refernces

• 1、 Lundhaug, Kamilla,Skatteb?l, Lars,Aasen, Arne J?rgen. "Synthesis of (1S,3R,5R,7S)-sordidin, the main component of the aggregation pheromone of the banana weevil Cosmopolites sordidus". . p. 100 - 102. Retrieved 2009.
• 2、 Jayaraman, Seetharaman,Ndiege, Isaiah O.,Oehlschlager, Allan C.,Gonzalez, Lilliana M.,Alpizar, Dennis,Falles, Mario,Budenberg, William J.,Ahuya, Peter. "Synthesis, analysis, and field activity of sordidin, a male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus". . p. 1145 - 1161. Retrieved 1997.
• 3、 Nakayama, Toru,Mori, Kenji. "Pheromone synthesis, CLXXXIV: Synthesis and absolute configuration of sordidin, the male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus". . p. 1075 - 1080. Retrieved 1997.
• 4、 Enders, Dieter,Breuer, Irene,Nuehring, Anja. "First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, aggregation pheromones of the banana weevil cosmopolites sordidus". . p. 2677 - 2683. Retrieved 2007/10/03.