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

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

 EINECS N/A
CAS No. 75917-90-7 Density 0.904 g/cm3
PSA 32.59000 LogP 4.62380
Solubility N/A Melting Point N/A
Formula C16H25NO Boiling Point 423.5 °C at 760 mmHg
Molecular Weight 247.381 Flash Point 259.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 75917-90-7 (DODECA-2E,4E,8Z,10E-TETRAENIC ACID ISOBUTYLAMIDE) Hazard Symbols N/A
Synonyms

2,4,8,10-Dodecatetraenamide,N-(2-methylpropyl)-, (E,E,E,Z)-;Dodeca-2E,4E,8Z,10E-tetraenoic acidisobutylamide;

Article Data 2

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

123-73-9

trans-Crotonaldehyde

98095-53-5

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

A

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

B

543-44-2

dodeca-2(E),4(E),8(E),10(E)-tetraenoic acid isobutylamide

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; dimethyl sulfoxide at 0℃; Yield given. Yields of byproduct given;
1308271-56-8

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

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
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
View Scheme
1308271-57-9

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

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
1.2: -78 - 20 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
2.2: 2 h / 0 °C
View Scheme

C10H14O

18498-20-9

2-N-iso-butyl-2-oxoethyl phosphonium chloride

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Stage #1: 2-N-iso-butyl-2-oxoethyl phosphonium chloride With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Wittig reaction;
Stage #2: C10H14O In tetrahydrofuran at 0℃; for 2h; Wittig reaction;
1308271-36-4

2-methyl-11-(tetrahydro-2H-pyran-2-yloxy)undeca-3,5-diyn-2-ol

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium hydroxide / toluene / 0.42 h / Reflux
2.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
3.2: -78 - 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
4.2: -78 °C
5.1: diisobutylaluminium hydride / diethyl ether / 0 °C
6.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
7.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
8.2: -78 - 20 °C
9.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
9.2: 2 h / 0 °C
View Scheme
171730-16-8

2-(nona-6,8-diynyloxy)tetrahydro-2H-pyran

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
2.2: -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
3.2: -78 °C
4.1: diisobutylaluminium hydride / diethyl ether / 0 °C
5.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
6.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
7.2: -78 - 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
8.2: 2 h / 0 °C
View Scheme
1027068-32-1

C9H10O

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
1.2: -78 °C
2.1: diisobutylaluminium hydride / diethyl ether / 0 °C
3.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
4.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
6.2: 2 h / 0 °C
View Scheme
1308271-41-1

10-methylundeca-6,8-diyne-1,10-diol

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydroxide / toluene / 0.42 h / Reflux
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
2.2: -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
3.2: -78 °C
4.1: diisobutylaluminium hydride / diethyl ether / 0 °C
5.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
6.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
7.2: -78 - 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
8.2: 2 h / 0 °C
View Scheme
18498-59-4

4-pentyn-1-al

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / diethyl ether; mineral oil / 0 °C
1.2: 0 °C
2.1: diisobutylaluminium hydride / diethyl ether / 0 °C
3.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
4.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
6.2: 2 h / 0 °C
View Scheme
101012-21-9, 139944-45-9

(2E)-hept-2-en-6-yn-1-ol

A

1308271-58-0

(2Z,4E,8Z,10E)-N-isobutyldodeca-2,4,8,10-tetraenamide

B

75917-90-7

N-isobutyl-2E,4E,8Z,10E-dodecatetraenamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: morpholine; palladium(II) chloride benzonitrile complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
2.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
4.2: 2 h / 0 °C
View Scheme

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

The 2,4,8,10-Dodecatetraenamide,N-(2-methylpropyl)-, (2E,4E,8Z,10E)-, with the CAS registry number 75917-90-7, is also known as Dodeca-2E,4E,8Z,10E-tetraenoic acidisobutylamide. It belongs to the product categories of Aromatic Carboxylic Acids; Amides; Anilides; Anhydrides & Salts. This chemical's molecular formula is C16H25NO and molecular weight is 247.3758. What's more, its systematic name and its IUPAC name are the same which is called (2E,4E,8Z,10E)-N-(2-Methylpropyl)dodeca-2,4,8,10-tetraenamide.

Physical properties about 2,4,8,10-Dodecatetraenamide,N-(2-methylpropyl)-, (2E,4E,8Z,10E)-: (1)ACD/LogP: 3.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.66; (4)ACD/LogD (pH 7.4): 3.66; (5)ACD/BCF (pH 5.5): 355.88; (6)ACD/BCF (pH 7.4): 355.88; (7)ACD/KOC (pH 5.5): 2332.55; (8)ACD/KOC (pH 7.4): 2332.55; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.496; (14)Molar Refractivity: 79.98 cm3; (15)Molar Volume: 273.4 cm3; (16)Surface Tension: 31.5 dyne/cm; (17)Density: 0.904 g/cm3; (18)Flash Point: 259.3 °C; (19)Enthalpy of Vaporization: 67.79 kJ/mol; (20)Boiling Point: 423.5 °C at 760 mmHg; (21)Vapour Pressure: 2.22E-07 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(\C=C\C=C\CC/C=C\C=C\C)NCC(C)C
(2)InChI: InChI=1/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-7,10-13,15H,8-9,14H2,1-3H3,(H,17,18)/b5-4+,7-6-,11-10+,13-12+
(3)InChIKey: VLGRWXYRKYWRPX-SRGJGADKBX

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