Acitral

Base Information

• Chemical Name: Acitral
• CAS No.: 877-60-1
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.263
• European Community (EC) Number: 618-064-9
• UNII: IH1N42114Z
• Nikkaji Number: J2.717.055B
• Wikidata: Q21546994
• Mol file: 877-60-1.mol

Synonyms:5-(2,2-Dimethylcyclopropyl)-3-methyl-2-pentenal;877-60-1;(+/-)-TRANS- AND CIS-5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-2-PENTENAL;Acitral;UNII-OO42EX51SR;FEMA No. 4105;SCHEMBL18338905;IH1N42114Z;FEMA NO. 4105, E-;3-Methyl-5-(2,2-dimethylcyclopropyl)-2-pentenal;(2E)-5-(2,2-dimethylcyclopropyl)-3-methyl-pentenal;2-Pentenal, 5-(2,2-dimethylcyclopropyl)-3-methyl-;Q21546994;(E)-5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-PENT-2-ENAL;5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-PENTENAL, (2E)-;(+/-) (E,Z)-5-(2,2-Dimethyl cyclopropyl)-3-methyl-2-pentenal;(+/-) (E,Z)-5-(2,2-Dimethylcyclopropyl)-3-methyl-2-pentenal;(E,Z)-5-(2,2-Dimethylcyclopropyl)-3-methyl-2-pentenal, (+/-)-;()-TRANS- AND CIS-5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-2-PENTENAL;(+/-)-5-(2,2-DIMETHYLCYCLOPROPYL)-3-METHYL-PENTENAL, (2E)-;(+/-)-trans- and cis-5-(2,2-Dimethylcyclopropyl)-3-methyl-2-pentenal [FIFH]

Chemical Property of Acitral

Chemical Property:

• PSA: 17.07000
• LogP: 2.95790
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 166.135765193
• Heavy Atom Count: 12
• Complexity: 201

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=O)CCC1CC1(C)C
• Isomeric SMILES: C/C(=C\C=O)/CCC1CC1(C)C

Technology Process of Acitral

There total 2 articles about Acitral 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:

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → 5-(2,2-dimethylcyclopropyl)-3-methylpent-2-enal (877-60-1)

Guidance literature:

diiodomethane; diethylzinc; In hexane; 1,2-dichloro-ethane; for 1.5h;

(E/Z)-3,7-dimethyl-2,6-octadienal; In hexane; 1,2-dichloro-ethane; at 20 ℃;

Reference yield:

→ 5-(2,2-dimethylcyclopropyl)-3-methylpent-2-enal (877-60-1)

Guidance literature:

entspr. Cyclopropan, Citral;

Reference yield:

5-(2,2-dimethylcyclopropyl)-3-methylpent-2-enal (877-60-1) → 1-((1SR,2RS)-4-(2-(2,2-dimethylcyclopropyl)ethyl)-1,2-dimethylcyclohex-3-enyl)ethanone

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran; diethyl ether / 0.75 h / 5 °C

2.1: pyridine / toluene / 18 h / 25 °C

3.1: 1,5-bis-(diphenylphosphino)pentane; palladium diacetate / 60 - 100 °C

4.1: boron trifluoride diethyl etherate / toluene / 0.33 h / -5 °C

4.2: 1 h / -5 °C

With pyridine; boron trifluoride diethyl etherate; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate; In tetrahydrofuran; diethyl ether; toluene; 4.2: Diels-Alder reaction;

DOI:10.1002/ejoc.201100528

upstream raw materials:

(E/Z)-3,7-dimethyl-2,6-octadienal

Refernces