Trimedlure B1

Base Information

• Chemical Name: Trimedlure B1
• CAS No.: 5748-20-9
• Molecular Formula: C12H21ClO2
• Molecular Weight: 232.7469
• UNII: RH591UGA6D
• Wikidata: Q27288115
• Mol file: 5748-20-9.mol

Synonyms:Trimedlure B1;UNII-RH591UGA6D;RH591UGA6D;5748-20-9;TML-B1;TRANS-TRIMEDLURE B1;Q27288115;CYCLOHEXANECARBOXYLIC ACID, 5-CHLORO-2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (1.ALPHA.,2.BETA.,5.ALPHA.)-;CYCLOHEXANECARBOXYLIC ACID, 5-CHLORO-2-METHYL-, 1,1-DIMETHYLETHYL ESTER, (1R,2R,5R)-REL-

Chemical Property of Trimedlure B1

Chemical Property:

• Vapor Pressure: 0.00302mmHg at 25°C
• Boiling Point: 284.2°Cat760mmHg
• Flash Point: 127.3°C
• PSA: 26.30000
• Density: 1.03g/cm³
• LogP: 3.37170
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 232.1230076
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC1C(=O)OC(C)(C)C)Cl
• Isomeric SMILES: C[C@@H]1CC[C@H](C[C@H]1C(=O)OC(C)(C)C)Cl

Technology Process of Trimedlure B1

There total 14 articles about Trimedlure B1 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:

(1S,6S)-6-Methyl-cyclohex-3-enecarbonyl chloride (92284-36-1) → (1S,2S,5R)-5-Chloro-2-methyl-cyclohexanecarboxylic acid tert-butyl ester (92344-64-4,5748-20-9,5748-22-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: 1) LDA 2) HMPT / 1) THF, 0 deg C 2) 25 deg C, 16h

3: HCl / tetrahydrofuran / 6 h / Heating

4: 40 percent / LAH / tetrahydrofuran / 16 h / Heating

5: 71 percent / Jones reagent

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; jones reagent; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00198a012

Reference yield:

(1S,6S)-6-Methyl-cyclohex-3-enecarbonyl chloride (92284-36-1) → 5t-Chlor-2t-methyl-cyclohexan-1r-carbonsaeure-tert-butylester (92344-63-3,5748-20-9,5748-22-1)

Guidance literature:

Multi-step reaction with 6 steps

2: 1) LDA 2) HMPT / 1) THF, 0 deg C 2) 25 deg C, 16h

3: HCl / tetrahydrofuran / 6 h / Heating

4: 40 percent / LAH / tetrahydrofuran / 16 h / Heating

5: 71 percent / Jones reagent

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; jones reagent; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00198a012

Reference yield:

(1R,6R)-6-Methyl-cyclohex-3-enecarboxylic acid ((S)-1-phenyl-ethyl)-amide (92284-47-4) → (1S,2S,5R)-5-Chloro-2-methyl-cyclohexanecarboxylic acid tert-butyl ester (92344-64-4,5748-20-9,5748-22-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) LDA 2) HMPT / 1) THF, 0 deg C 2) 25 deg C, 16h

2: HCl / tetrahydrofuran / 6 h / Heating

3: 40 percent / LAH / tetrahydrofuran / 16 h / Heating

4: 71 percent / Jones reagent

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; jones reagent; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00198a012

upstream raw materials:

(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid

tert-butyl alcohol

1R,6R-(+)-6-Methyl-3-cyclohexenyl-methanol

(1S,6S)-6-Methyl-cyclohex-3-enecarbonyl chloride

Downstream raw materials:

6-methylcyclohex-1-ene-1-carboxylic acid

trans-6-Methyl-cyclohex-3-en-carbonsaeure-tert-butylester

2-Methyl-bicyclo<3,1,0>hexan-1-carbonsaeure-tert.-butylester

tert-butyl (RS)-6-methyl-cyclohex-1-ene-carboxylate

Refernces

• 1、 Sonnet, Philip E.,McGovern, Terrence P.,Cunningham, Roy T.. "Enantiomers of the Biologically Active Components of the Insect Attractant Trimedlure". . p. 4639 - 4643. Retrieved 2007/10/02.