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19945-61-0 Usage

Definition

ChEBI: An alkatriene consisting of 4,8-dimethylnonane having the three double bonds in the 1-, 3- and 7-positions.

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 2254, 1978 DOI: 10.1021/ja00475a059Tetrahedron Letters, 35, p. 5453, 1994 DOI: 10.1016/S0040-4039(00)73523-4

Check Digit Verification of cas no

The CAS Registry Mumber 19945-61-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,9,4 and 5 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 19945-61:
(7*1)+(6*9)+(5*9)+(4*4)+(3*5)+(2*6)+(1*1)=150
150 % 10 = 0
So 19945-61-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H18/c1-5-7-11(4)9-6-8-10(2)3/h5,7-8H,1,6,9H2,2-4H3/b11-7+

19945-61-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-4,8-dimethyl-1,3,7-nonatriene

1.2 Other means of identification

Product number -
Other names DMNT

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19945-61-0 SDS

19945-61-0Synthetic route

3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 25℃;92%
With potassium tert-butylate In dichloromethane Wittig reaction; Inert atmosphere;84%
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 25℃; for 1h;
Stage #2: 3,7-dimethyl-2,6-octadienal In tetrahydrofuran at 25℃; for 6h; Wittig reaction;
77%
geranyl mesylate
78130-96-8

geranyl mesylate

methylenetriphenylarsorane
47025-43-4, 19365-61-8

methylenetriphenylarsorane

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane for 1h; Ambient temperature;91%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

MePPh3Br

MePPh3Br

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran Condensation;90%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With Wilkinson's catalyst; triphenylphosphine; isopropyl alcohol In tetrahydrofuran at 25℃; for 2h;90%
With triphenylphosphine; isopropyl alcohol; RhCl(PPh3)3 In tetrahydrofuran at 25℃;90%
With (IMes)CuCl; triphenylphosphine; isopropyl alcohol In 1,4-dioxane; diethyl ether at 60℃; for 16h;74%
dibromo-1,1 dimethyl-4,8 nonadiene-3 E, 7
105865-47-2

dibromo-1,1 dimethyl-4,8 nonadiene-3 E, 7

A

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

B

2-Methyl-2-(4-methyl-pent-3-enyl)-bicyclo[1.1.0]butane
105865-53-0

2-Methyl-2-(4-methyl-pent-3-enyl)-bicyclo[1.1.0]butane

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at -30℃;A 89%
B 10%
geranyl mesylate
78130-96-8

geranyl mesylate

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium; lithium iodide In tetrahydrofuran; hexane from 0 degC to room temp.;85%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Stage #1: methyl-triphenylphosphonium iodide With phenyllithium In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere; Cooling with ice;
Stage #2: 3,7-dimethyl-2,6-octadienal In tetrahydrofuran; diethyl ether; cyclohexane at 0 - 20℃; for 2h; Inert atmosphere;
80%
Stage #1: methyl-triphenylphosphonium iodide With phenyllithium In tetrahydrofuran; hexane at 0 - 20℃;
Stage #2: 3,7-dimethyl-2,6-octadienal In tetrahydrofuran; hexane at 0 - 20℃;
60 g
With potassium tert-butylate In tetrahydrofuran Wittig Olefination;
Geraniol
106-24-1

Geraniol

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Stage #1: Geraniol With 1,10-Phenanthroline; potassium tert-butylate; copper(l) chloride In fluorobenzene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With 1-methyl-1H-imidazole; di-tert-butyl-diazodicarboxylate; oxygen In fluorobenzene Reflux;
Stage #3: diazomethyl-trimethyl-silane With triphenylphosphine; isopropyl alcohol In fluorobenzene; diethyl ether at 60℃; Inert atmosphere;
74%
3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene
81678-25-3

3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene

A

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

B

1-Methyl-2-tributylstannanylmethylsulfanyl-1H-imidazole
82895-46-3

1-Methyl-2-tributylstannanylmethylsulfanyl-1H-imidazole

C

2-((E)-3,7-Dimethyl-1-tributylstannanyl-octa-2,6-dienylsulfanyl)-1-methyl-1H-imidazole
82895-45-2

2-((E)-3,7-Dimethyl-1-tributylstannanyl-octa-2,6-dienylsulfanyl)-1-methyl-1H-imidazole

Conditions
ConditionsYield
With n-butyllithium; tri-n-butylstannylmethyl iodide Product distribution;A 45%
B 43%
C 31%
With n-butyllithium; tri-n-butylstannylmethyl iodide Yield given. Multistep reaction;A n/a
B 43%
C 31%
Vinyl bromide
593-60-2

Vinyl bromide

2-methylhept-2-en-6-yne
22842-10-0

2-methylhept-2-en-6-yne

trimethylaluminum
75-24-1

trimethylaluminum

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
(i) Zr catalyst, (ii) /BRN= 1361370/, Pd(PPh3)2Cl2, iBu2AlH, ZnCl2; Multistep reaction;
diiodomethane
75-11-6

diiodomethane

cis-3,7-dimethyl-2,6-octadienal
106-26-3

cis-3,7-dimethyl-2,6-octadienal

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With trimethylaluminum; zinc In tetrahydrofuran; hexane
homogeranyl bromide
69405-35-2

homogeranyl bromide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With potassium hydroxide In methanol for 2h; Heating;
geranyl phenyl sulfone
56691-80-6

geranyl phenyl sulfone

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium; tri-n-butylstannylmethyl iodide 1.) THF, -78 deg C, 2.) -78 deg C, 1 h; Yield given. Multistep reaction;
2-[(2E)-3,7-dimethyl-2,6-octadienyl]sulfanylpyridine
82895-40-7

2-[(2E)-3,7-dimethyl-2,6-octadienyl]sulfanylpyridine

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium; tri-n-butylstannylmethyl iodide 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 20 min and 0 deg C 1.5 h; Yield given. Multistep reaction;
With n-butyllithium; tri-n-butylstannylmethyl iodide 1) hexane, THF, -78 deg C, 30 min; 2) hexane, THF, -78 de C, 20 min; o deg C, 10 min; Yield given. Multistep reaction;
3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene
81678-25-3

3,7-dimethyl-1-(N-methyl-2-imidazolylthio)-2,6-octadiene

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Yield given. Multistep reaction;
((E)-2-Benzenesulfonyl-4,8-dimethyl-nona-3,7-dienyl)-trimethyl-silane

((E)-2-Benzenesulfonyl-4,8-dimethyl-nona-3,7-dienyl)-trimethyl-silane

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With fluoride Yield given;
Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

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

A

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

B

(3Z)-4,8-dimethylnona-1,3,7-triene
21214-62-0

(3Z)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Yield given. Yields of byproduct given;
C14H27(2)HSi

C14H27(2)HSi

A

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

B

(3Z)-4,8-dimethylnona-1,3,7-triene
21214-62-0

(3Z)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With P450 enzyme; Phaseolus lunatus Yield given. Yields of byproduct given;
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
In tetrahydrofuran Substitution;
Wittig Olefination;
geranyl phenyl sulfone
56691-80-6

geranyl phenyl sulfone

(tributylstannyl)methyl iodide

(tributylstannyl)methyl iodide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With n-butyllithium; ammonium chloride 1) hexane, THF, -78 deg C, 95 min; Yield given. Multistep reaction;
2-((phenylsulfonyl)methyl)prop-2-enylphenylsulfone
92531-85-6

2-((phenylsulfonyl)methyl)prop-2-enylphenylsulfone

(tributylstannyl)methyl iodide

(tributylstannyl)methyl iodide

A

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

B

2,6-dimethyl-8-(2-pyridylthio)-2,6-dodecadiene
82895-44-1

2,6-dimethyl-8-(2-pyridylthio)-2,6-dodecadiene

Conditions
ConditionsYield
With n-butyllithium; ammonium chloride 1) hexane, THF, -78 deg C, 60 min; RT, 1 h; Yield given. Multistep reaction;
Geraniol
106-24-1

Geraniol

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 7 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2 / -10 °C
2: 92 percent / NaHMDS / tetrahydrofuran / 0 - 25 °C
View Scheme
Multi-step reaction with 2 steps
1: (COCl)2; DMSO / CH2Cl2
2: tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / acetonitrile / 3 h / 0 °C / pH 7 / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
View Scheme
Geraniol
106-24-1

Geraniol

sodium ammonium

sodium ammonium

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / MnO2 / CH2Cl2
2: 90 percent / n-BuLi / tetrahydrofuran
View Scheme
1-chloro-3,7-dimethylocta-2,6-diene
5389-87-7

1-chloro-3,7-dimethylocta-2,6-diene

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / tetrabutylammonium bromide / tetrahydrofuran / 17 h / Ambient temperature
2: 1) butyllithium; 2) aq. NH4Cl / 1) hexane, THF, -78 deg C, 95 min
View Scheme
Multi-step reaction with 2 steps
1: butan-2-one
View Scheme
Multi-step reaction with 2 steps
2: 1.) n-butyllithium(in hexane), 2.) tri-n-butylstannylmethyl iodide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 20 min and 0 deg C 1.5 h
View Scheme
Multi-step reaction with 2 steps
1: tetrabutylammonium bromide
2: 1.) n-butyllithium(in hexane), 2.) tri-n-butylstannylmethyl iodide / 1.) THF, -78 deg C, 2.) -78 deg C, 1 h
View Scheme
1-bromo-4-methylpent-3-ene
2270-59-9

1-bromo-4-methylpent-3-ene

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) Mg, Et2O, (ii) /BRN= 1633817/
2: aq. HBr / 0.5 h / 10 - 15 °C
3: KOH / methanol / 2 h / Heating
View Scheme
2-cyclopropyl-6-methyl-hept-5-en-2-ol
65017-88-1

2-cyclopropyl-6-methyl-hept-5-en-2-ol

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HBr / 0.5 h / 10 - 15 °C
2: KOH / methanol / 2 h / Heating
View Scheme
manganese dioxide
1313-13-9

manganese dioxide

Geraniol
106-24-1

Geraniol

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
In dichloromethane
3-methyl-2,5-dihydrothiophen-1,1-dioxide
1193-10-8

3-methyl-2,5-dihydrothiophen-1,1-dioxide

2,3-dihydrothiophene-1,1-dioxide
1192-16-1

2,3-dihydrothiophene-1,1-dioxide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; water
formaldehyd
50-00-0

formaldehyd

triethylgeranylphosphonium bromide

triethylgeranylphosphonium bromide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

Conditions
ConditionsYield
With potassium carbonate In water at 100℃; for 0.0833333h; Wittig reaction; Microwave irradiation;
non-8-en-1-ol
13038-21-6

non-8-en-1-ol

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

(8Z,10E)-11,15-dimethylhexadeca-8,10,14-trien-1-ol

(8Z,10E)-11,15-dimethylhexadeca-8,10,14-trien-1-ol

Conditions
ConditionsYield
With C35H47N3O4Ru In neat (no solvent) at 50℃; for 24h; Cross Metathesis; Inert atmosphere; chemoselective reaction;95%
(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

(E)-4,8-dimethylnona-3,7-dien-1-ol
459-88-1

(E)-4,8-dimethylnona-3,7-dien-1-ol

Conditions
ConditionsYield
Stage #1: (E)-4,8-dimethylnona-1,3,7-triene With disiamylborane In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; ethanol at 0 - 20℃; for 3h; Inert atmosphere; stereoselective reaction;
91%
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide In tetrahydrofuran at 0℃;75%
With sodium hydroxide; (Si1)2BH; dihydrogen peroxide In tetrahydrofuran Addition;
Stage #1: (E)-4,8-dimethylnona-1,3,7-triene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran
Stage #2: With dihydrogen peroxide
hydrogen cyanide
74-90-8

hydrogen cyanide

(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

2,6-dimethyl-2-propenyl-hept-5-enenitrile

2,6-dimethyl-2-propenyl-hept-5-enenitrile

Conditions
ConditionsYield
rac-1,2-trans-bis-(diphenylphosphinooxy)cyclohexane; bis(1,5-cyclooctadiene)nickel (0) In toluene at 50℃; for 24h;83%
(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

(E)-2-bromo-6-methylocta-2,6-diene-1,8-diol
318967-93-0

(E)-2-bromo-6-methylocta-2,6-diene-1,8-diol

plaunotol
64218-02-6

plaunotol

Conditions
ConditionsYield
Stage #1: (E)-4,8-dimethylnona-1,3,7-triene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 20℃; for 4h; Reduction;
Stage #2: (E)-2-bromo-6-methylocta-2,6-diene-1,8-diol With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 2.5h; Suzuki coupling;
77%
(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

(E)-2,2-dimethyl-3-(3-methylhexa-3,5-dienyl) oxirane
168113-15-3

(E)-2,2-dimethyl-3-(3-methylhexa-3,5-dienyl) oxirane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;75%
(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

(Z)-β-bromocrotyl alcohol 2-tetrahydropyranyl ether
117582-50-0

(Z)-β-bromocrotyl alcohol 2-tetrahydropyranyl ether

9-bora-bicyclo[3.3.1]nonane
280-64-8

9-bora-bicyclo[3.3.1]nonane

(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol 2-tetrahydropyranyl ether
110990-63-1

(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol 2-tetrahydropyranyl ether

Conditions
ConditionsYield
With sodium hydroxide; cis-dichloro-1,1'-bis(diphenylphosphino)ferrocene palladium(II) In tetrahydrofuran; N,N-dimethyl-formamide To a soln. of triene is added a soln. of 9-BBN at 0°C over 10 min, mixt. stirred for 1 h at 0°C, then for 4 h at room temp., addn. of soln. of bromocrotyl ether, catalyst and NaOH, after heating at 50°C for 8 h poured into water.; Extracted with benzene, washed with water, dried (MgSO4), chromy. over silica gel with benzene-acetate, final product is identified by (1)H NMR, IR, elem. anal.;67%
(E)-4,8-dimethylnona-1,3,7-triene
19945-61-0

(E)-4,8-dimethylnona-1,3,7-triene

methyl 2-diazobut-3-enoate
126554-35-6

methyl 2-diazobut-3-enoate

4-methyl-4-(4-methyl-pent-3-enyl)-cyclohepta-1,5-dienecarboxylic acid methyl ester

4-methyl-4-(4-methyl-pent-3-enyl)-cyclohepta-1,5-dienecarboxylic acid methyl ester

Conditions
ConditionsYield
With Rh2(S-PTAD)4 In hexane; toluene at 20℃; Reflux;67%
Conditions
ConditionsYield
With dibenzyl diselenide In tetrahydrofuran; acetonitrile at 20℃; for 18h; regioselective reaction;66%

19945-61-0Downstream Products

19945-61-0Relevant articles and documents

Olefination of activated halides and mesylates using arsonium ylides

Seyer, Andre,Alcaraz, Lilian,Mioskowski

, p. 7871 - 7874 (1997)

Alkyltriphenylarsonium ylides react with activated primary halides and mesylates to afford olefins in good yields and with high E-selectivity.

Biosynthesis of C11 and C16 homoterpenes in higher plants; stereo- chemistry of the C-C-bond cleavage reaction

Boland, Wilhelm,Gaebler, Andreas,Gilbert, Matthias,Feng, Zhuofu

, p. 14725 - 14736 (1998)

In higher plants the C11 homoterpene 4,8-dimethylnona-1,3,7-triene (1) originates from oxidative degradation of nerolidol (3) or geranylacetone (4). The geometry of the transition state of bond cleavage has been shown to be syn-periplanar, for both 3 and 4 by application of chirally labelled, deuterated precursors to flowers of Magnolia liliiflora nigra or leaves of the Lima bean Phaseolus lunatus. The synthesis of the deuterated, chiral metabolic probes 3 and 8 from nor-farnesene (5), via the enantiomeric epoxides (2S,3R)-6 and ent-6, is described.

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Negishi,E. et al.

, p. 2254 - 2256 (1978)

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Highly Selective and Catalytic Generation of Acyclic Quaternary Carbon Stereocenters via Functionalization of 1,3-Dienes with CO2

Chen, Xiao-Wang,Zhu, Lei,Gui, Yong-Yuan,Jing, Ke,Jiang, Yuan-Xu,Bo, Zhi-Yu,Lan, Yu,Li, Jing,Yu, Da-Gang

, p. 18825 - 18835 (2019/11/28)

The catalytic asymmetric functionalization of readily available 1,3-dienes is highly important, but current examples are mostly limited to the construction of tertiary chiral centers. The asymmetric generation of acyclic products containing all-carbon quaternary stereocenters from substituted 1,3-dienes represents a more challenging, but highly desirable, synthetic process for which there are very few examples. Herein, we report the highly selective copper-catalyzed generation of chiral all-carbon acyclic quaternary stereocenters via functionalization of 1,3-dienes with CO2. A variety of readily available 1,1-disubstituted 1,3-dienes, as well as a 1,3,5-triene, undergo reductive hydroxymethylation with high chemo-, regio-, E/Z-, and enantioselectivities. The reported method features good functional group tolerance, is readily scaled up to at least 5 mmol of starting diene, and generates chiral products that are useful building blocks for further derivatization. Systemic mechanistic investigations using density functional theory calculations were performed and provided the first theoretical investigation for an asymmetric transformation involving CO2. These computational results indicate that the 1,2-hydrocupration of 1,3-diene proceeds with high π-facial selectivity to generate an (S)-allylcopper intermediate, which further induces the chirality of the quaternary carbon center in the final product. The 1,4-addition of an internal allylcopper complex, which differs from previous reports involving terminal allylmetallic intermediates, to CO2 kinetically determines the E/Z- and regioselectivity. The rapid reduction of a copper carboxylate intermediate to the corresponding silyl-ether in the presence of Me(MeO)2SiH provides the exergonic impetus and leads to chemoselective hydroxymethylation rather than carboxylation. These results provide new insights for guiding further development of asymmetric C-C bond formations with CO2

Catalytic enantioselective 1,2-diboration of 1,3-dienes: Versatile reagents for stereoselective allylation

Kliman, Laura T.,Mlynarski, Scott N.,Ferris, Grace E.,Morken, James P.

, p. 521 - 524 (2012/03/11)

More with boron: The development of catalytic enantioselective 1,2-diboration of 1,3-dienes enables a new strategy for enantioselective carbonyl allylation reactions (see scheme). These reactions occur with outstanding levels of stereoselection and can be applied to both monosubstituted and 1,1-disubstituted dienes. The carbonyl allylation reactions provide enantiomerically enriched functionalized homoallylic alcohol products. Copyright

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