(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

Base Information

• Chemical Name: (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
• CAS No.: 23726-92-3
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• Hs Code.: 2914299000
• European Community (EC) Number: 245-843-7
• UNII: 074X5R04IQ
• DSSTox Substance ID: DTXSID6051487
• Nikkaji Number: J242.653F
• Wikidata: Q27236260
• Mol file: 23726-92-3.mol

Synonyms:2-Buten-1-one,1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (Z)- (8CI);(Z)-b-Damascone;

Chemical Property of (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

Chemical Property:

• Vapor Pressure: 0.00655mmHg at 25°C
• Refractive Index: n20/D 1.498
• Boiling Point: 271.2 ºC at 760 mmHg
• Flash Point: 108 ºC
• PSA: 17.07000
• Density: 0.907 g/cm³
• LogP: 3.65820
• Storage Temp.: 2-8°C
• Water Solubility.: 192.3mg/L(temperature not stated)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(CCCC1(C)C)C
• Isomeric SMILES: C/C=C\C(=O)C1=C(CCCC1(C)C)C
• Uses: A food spice that can be used to formulate rose essence.

Technology Process of (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

There total 10 articles about (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one 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:

4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol (49815-59-0) → beta damascone (23726-91-2) + (Z)-1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (23726-92-3) + 1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (31089-73-3)

Guidance literature:

With potassium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19870700721

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → (Z)-1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (23726-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 52 percent / NaOH, H₂O₂ / methanol; H₂O

2: 96 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.08 h / 0 °C

3: 89 percent / CBr₄, PPh₃ / pyridine / 12 h / 0 °C

4: 80 percent / Zn, CuI / aq. ethanol / sonication

5: 1.) MnO₂; 2.) p-TsOH / 1.) pentane, 24 h; 2.) THF, reflux, 4 h

With manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; carbon tetrabromide; dihydrogen peroxide; toluene-4-sulfonic acid; triphenylphosphine; zinc; In pyridine; methanol; ethanol; water;

DOI:10.1021/jo00035a045

Reference yield:

2-(1-Bromoethyl)-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)oxirane (139609-04-4,139686-52-5) → (Z)-1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (23726-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Zn, CuI / aq. ethanol / sonication

2: 1.) MnO₂; 2.) p-TsOH / 1.) pentane, 24 h; 2.) THF, reflux, 4 h

With manganese(IV) oxide; copper(l) iodide; toluene-4-sulfonic acid; zinc; In ethanol;

DOI:10.1021/jo00035a045

upstream raw materials:

6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester

allylmagnesium bromide

2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol

4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol

Refernces

• 1、 Snowden, Roger L.,Linder, Simon M.,Muller, Bernard L.,Schulte, Karl H.. "172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone". . p. 1858 - 1878. Retrieved 2007/10/02.
• 2、 Visser, Cornelis P.,Cerfontain, Hans. "Photochemistry of dienones. Part 12. Photochemistry of (E)-α- and (E)-β-damascone". . p. 307 - 311. Retrieved 2007/10/02.