(2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

Base Information

• Chemical Name: (2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal
• CAS No.: 54226-17-4
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• UNII: HF36R5J7B2
• DSSTox Substance ID: DTXSID30431944
• Wikidata: Q82245986
• Mol file: 54226-17-4.mol

Synonyms:54226-17-4;(2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienal;HF36R5J7B2;(2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal;(2Z,4E)-3-METHYL-5-(2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)PENTA-2,4-DIENAL;2,4-Pentadienal, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2Z,4E)-;(7E,9Z)-|A-Ionylidene Acetaldehyde;UNII-HF36R5J7B2;SCHEMBL8565948;DTXSID30431944;OPSSCPNCFKJCFR-GHYOLMRSSA-N;(7E,9Z)-beta-Ionylideneacetaldehyde;beta-Ionylideneacetaldehyde, (7E,9Z)-;(7E,9Z)-.BETA.-IONYLIDENEACETALDEHYDE;.BETA.-IONYLIDENEACETALDEHYDE, (7E,9Z)-

Chemical Property of (2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

Chemical Property:

• Boiling Point: 329.1±11.0 °C(Predicted)
• PSA: 17.07000
• Density: 0.948±0.06 g/cm3(Predicted)
• LogP: 4.21440
• Solubility.: Acetone, Chloroform, Dichloromethane, Ether, Ethyl Acetate
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 354

Purity/Quality:

97% ^*data from raw suppliers

(7E,9Z)-β-IonylideneAcetaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=O)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=O)/C
• Uses: Intermediate in the preparation of Retinoic Acid derivatives.

Technology Process of (2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

There total 41 articles about (2Z,4E)-3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 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: 75.0%

(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol (3917-40-6) → (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal (54226-17-4)

Guidance literature:

With manganese(IV) oxide; In diethyl ether; for 4h;

DOI:10.1016/j.bmc.2004.04.047

Reference yield:

ethyl 4-bromo-3-methylcrotonate (51318-62-8,51371-55-2,26918-14-9) → (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal (54226-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc / tetrahydrofuran / Reflux; Inert atmosphere

2: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / -78 - -40 °C

3: hydrogenchloride / 1,2-dichloro-ethane; water / 12.5 h / 40 °C

With hydrogenchloride; diisobutylaluminium hydride; zinc; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: |Reformatsky Reaction;

Reference yield:

3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile (105175-91-5) → (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal (3917-41-7) + (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal (54226-17-4)

Guidance literature:

With diisobutylaluminium hydride; tartaric acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, THF, 0 -> 40-45 deg C, 1 h, 2.) room temperature, 2 h;

upstream raw materials:

(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

3-methyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-penta-2,4-dienenitrile

9-hydroxy-β-ionylideneacetaldehyde dimethyl acetal

Downstream raw materials:

9-cis-retinoic acid

9,13-di-cis-retinoic acid

(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid

6-methyl-8t-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3t,5c,7-trien-2-one

Refernces

• 1、 Maj, Jadwiga,Morzycki, Jacek W.,Rárová, Lucie,Wasilewski, Grzegorz,Wojtkielewicz, Agnieszka. "A cross-metathesis approach to the synthesis of new etretinate type retinoids, ethyl retinoate and its 9Z-isomer". supporting information. p. 5430 - 5433. Retrieved 2012/11/07.
• 2、 Wada, Akimori,Fukunaga, Kouki,Ito, Masayoshi,Mizuguchi, Yukari,Nakagawa, Kimie,Okano, Toshio. "Preparation and biological activity of 13-substituted retinoic acids". . p. 3931 - 3942. Retrieved 2007/10/03.