2,4,8,10-Dodecatetraenamide, N-(2-methylpropyl)-, (2E,4E,8Z,10E)-

Base Information

• Chemical Name: 2,4,8,10-Dodecatetraenamide, N-(2-methylpropyl)-, (2E,4E,8Z,10E)-
• CAS No.: 75917-90-7
• Molecular Formula: C16H25NO
• Molecular Weight: 247.381
• Hs Code.: 2924199090
• UNII: NXV62B426A
• Nikkaji Number: J1.573.631C
• Wikidata: Q27285097
• Metabolomics Workbench ID: 136272
• ChEMBL ID: CHEMBL463345
• Mol file: 75917-90-7.mol

Synonyms:(2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide;N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide

Chemical Property of 2,4,8,10-Dodecatetraenamide, N-(2-methylpropyl)-, (2E,4E,8Z,10E)-

Chemical Property:

• Vapor Pressure: 2.22E-07mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 423.5 °C at 760 mmHg
• Flash Point: 259.3 °C
• PSA: 32.59000
• Density: 0.904 g/cm³
• LogP: 4.62380
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 247.193614421
• Heavy Atom Count: 18
• Complexity: 322

Purity/Quality:

99%, ^*data from raw suppliers

Dodeca-2E,4E,8Z,10E-tetraenoicAcidIsobutylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2,4,8,10-Dodecatetraenamide, N-(2-methylpropyl)-, (2E,4E,8Z,10E)-

There total 13 articles about 2,4,8,10-Dodecatetraenamide, N-(2-methylpropyl)-, (2E,4E,8Z,10E)- 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:

trans-Crotonaldehyde (123-73-9,4170-30-3) + (2E,4E)-8-(Triphenyl-λ5-phosphanylidene)-octa-2,4-dienoic acid isobutyl-amide (98095-53-5) → N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide (75917-90-7) + dodeca-2(E),4(E),8(E),10(E)-tetraenoic acid isobutylamide (543-44-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)94859-7

Reference yield:

C10H14O + 2-N-iso-butyl-2-oxoethyl phosphonium chloride (18498-20-9) → (2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide (1308271-58-0) + N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide (75917-90-7)

Guidance literature:

2-N-iso-butyl-2-oxoethyl phosphonium chloride; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.5h;

C₁₀H₁₄O; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo200289f

Reference yield:

(2E,8E)-deca-2,8-dien-6-yn-1-ol (1308271-56-8) → (2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide (1308271-58-0) + N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide (75917-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C

2.2: -78 - 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C

3.2: 2 h / 0 °C

With oxalyl dichloride; naphthalene; potassium tert-butylate; lithium; dimethyl sulfoxide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction;

DOI:10.1021/jo200289f

upstream raw materials:

trans-Crotonaldehyde

(2E,4E)-8-(Triphenyl-λ⁵-phosphanylidene)-octa-2,4-dienoic acid isobutyl-amide

(2E,8E)-deca-2,8-dien-6-yn-1-ol

(2E,6Z,8E)-deca-2,6,8-trien-1-ol

Refernces

• 1、 Crombie, Leslie,Fisher, David. "SYNTHESIS OF NATURAL POLYENE ISOBUTYLAMIDES. STEREOCHEMISTRY OF THE WITTIG REACTIONS". . p. 2481 - 2484. Retrieved 2007/10/02.