2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

Base Information

• Chemical Name: 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
• CAS No.: 472-66-2
• Molecular Formula: C11H18O
• Molecular Weight: 166.263
• Hs Code.: 2912299000
• European Community (EC) Number: 207-454-0
• UNII: CQ51RNO61H
• DSSTox Substance ID: DTXSID0047088
• Nikkaji Number: J196.191H
• Wikidata: Q27275648
• Metabolomics Workbench ID: 45588
• ChEMBL ID: CHEMBL3184950
• Mol file: 472-66-2.mol

Synonyms:2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde;472-66-2;beta-Homocyclocitral;2-(2,6,6-trimethylcyclohexen-1-yl)acetaldehyde;2,6,6-Trimethyl-1-cyclohexen-1-acetaldehyde;beta-Cyclohomocitral;1-CYCLOHEXENE-1-ACETALDEHYDE, 2,6,6-TRIMETHYL-;FEMA No. 3474;beta-Apo-8-carotenal;Cyclohomocitral, beta-;Apo-8-carotenal, beta-;UNII-CQ51RNO61H;ghl.PD_Mitscher_leg0.59;CQ51RNO61H;DTXSID0047088;EINECS 207-454-0;2-(2,6,6-trimethylcyclohex-1-enyl)acetaldehyde;2-(2,6,6-trimethylcyclohex-1-en-1-yl)acetaldehyde;ss-Homocyclocitral;Homocyclocitral, beta-;.BETA.-HOMOCYCLOCITRAL;SCHEMBL881427;.BETA.-APO-8-CAROTENAL;CHEMBL3184950;DTXCID8027088;HOMOCYCLOCITRAL, .BETA.-;CHEBI:171820;Tox21_302284;MFCD00012057;AKOS015912952;NCGC00256023-01;AS-66249;CAS-472-66-2;(266-Trimethyl-1-cyclohexenyl)acetaldehyde;266-Trimethyl-1-cyclohexene-1-acetaldehyde;FT-0691466;(2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde;2-(266-Trimethylcyclohex-1-enyl)acetaldehyde;2,6,6-Trimethyl-1-cyclohexane-1-acetaldehyde;2-(2,6,6-trimethyl-1-cyclohexenyl)acetaldehyde;(2,6,6-Trimethyl-1-cyclohexen-1-yl)acetaldehyde;(2,6,6-Trimethyl-1-cyclohexen-1-yl)acetaldehyde #;Q27275648;2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde, >=75%;2,6,6 - trimethyl - 1 - cyclohexene - 1 - acetaldehyde;2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-ACETALDEHYDE [FHFI];2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde, technical grade, 80%

Chemical Property of 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

Chemical Property:

• Vapor Pressure: 0.0324mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Boiling Point: 243.3 °C at 760 mmHg
• Flash Point: 76.8 °C
• PSA: 17.07000
• Density: 0.879 g/cm³
• LogP: 3.10200
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 166.135765193
• Heavy Atom Count: 12
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

beta-Homocyclocitral ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)CC=O
• Uses: 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde can be used as a starting material to prepare: (±)-Aeginetolide by oxidation in the presence of meta-chloroperoxybenzoic acid (m-CPBA). (±)-Dihydroactinidiolide (a C11-terpenic lactone) via dehydration of key intermediate aeginetolide. It can also be used as a key intermediate to synthesize drimane-related sesquiterpenes and substituted retinoic acid analogs.

Technology Process of 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

There total 20 articles about 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde 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: 94.0%

2-((E)-2-Methoxy-vinyl)-1,3,3-trimethyl-cyclohexene (86558-54-5,86558-55-6) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Guidance literature:

With perchloric acid; In tetrahydrofuran; for 0.5h; Ambient temperature;

Reference yield: 93.7%

2,2,6-trimethylcyclohexan-1-one (2408-37-9) + Bromoacetaldehyde diethyl acetal (2032-35-1) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Guidance literature:

Bromoacetaldehyde diethyl acetal; With iodine; magnesium; In tetrahydrofuran; at 30 - 35 ℃; for 3.25h; Inert atmosphere;

2,2,6-trimethylcyclohexan-1-one; In tetrahydrofuran; at 10 - 15 ℃; for 3h;

Reference yield: 93.1%

2-bromomethyl-1,3-dioxolane (4360-63-8) + 2,2,6-trimethylcyclohexan-1-one (2408-37-9) → (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde (472-66-2)

Guidance literature:

2-bromomethyl-1,3-dioxolane; With iodine; magnesium; In 2-methyltetrahydrofuran; at 30 - 40 ℃; for 3.25h; Inert atmosphere;

2,2,6-trimethylcyclohexan-1-one; In 2-methyltetrahydrofuran; at 10 - 15 ℃; for 3h;

upstream raw materials:

1-ethoxyethynyl-2,2,6-trimethyl-cyclohexanol

2-acetoxyvinylidene-1,1,3-trimethyl-cyclohexane

1-ethynyl-2,2,6-trimethyl-1-cyclohexanol

ethanethiol

Downstream raw materials:

2,4,4-trimethyl-3-(2'-hydroxymethyl)-2-cyclohexene

1-<2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl>pyrrolidine

Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1

(2,6,6-trimethylcyclohex-1-enyl)acetic acid

Refernces

• 1、 -. "Derivatives of erythromycylamine". . . Retrieved 2008/06/13.
• 2、 Lee, Eun,Shin, In-Jae,Kim, Tae-Seong. "Enantiocontrolled synthesis of quaternary carbon centers via anionic oxy-cope rearrengement: An efficient synthesis of (+)-dihydromayurone". . p. 260 - 264. Retrieved 2007/10/02.