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(Z)-8-DODECEN-1-YL ACETATE, also known as (8Z)-Dodecenyl Acetate, is a chemical compound derived from 1-Pentyne, which is used as a reagent in the synthesis of various bioactive molecules. It is a white to pale yellow solid with unique chemical properties that make it suitable for various applications across different industries.

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  • 28079-04-1 Structure
  • Basic information

    1. Product Name: (Z)-8-DODECEN-1-YL ACETATE
    2. Synonyms: (8Z)-8-Dodecenyl acetate;(Z)-8-Dodecen-1-ol acetate;8-Dodecen-1-ol, acetate, (Z)-;acetate,(z)-8-dodecen-1-o;z-8-dodecenyl;z-8-dodecenylacetate;(Z)-8-DODECEN-1-YL ACETATE;CIS-8-DODECEN-1-OL ACETATE
    3. CAS NO:28079-04-1
    4. Molecular Formula: C14H26O2
    5. Molecular Weight: 226.36
    6. EINECS: 248-823-6
    7. Product Categories: insect pheromone
    8. Mol File: 28079-04-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 300.1 °C at 760 mmHg
    3. Flash Point: 96.5 °C
    4. Appearance: /
    5. Density: 0.881
    6. Vapor Pressure: 0.00114mmHg at 25°C
    7. Refractive Index: 1.448
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSO (Slightly), Water (Slightly)
    10. Stability: Very Hygroscopic
    11. CAS DataBase Reference: (Z)-8-DODECEN-1-YL ACETATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)
    13. EPA Substance Registry System: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 28079-04-1(Hazardous Substances Data)

28079-04-1 Usage

Uses

Used in Pharmaceutical Industry:
(Z)-8-DODECEN-1-YL ACETATE is used as an active pharmaceutical ingredient for its antibacterial properties. It inhibits protein synthesis by binding to the L6 protein of the 50S ribosomal subunit, making it a potential candidate for the development of new antibiotics.
Used in Chemical Synthesis:
(Z)-8-DODECEN-1-YL ACETATE is used as a reagent for the synthesis of novel 1,2,3-triazole-1,4-benzoxazine hybrids, which exhibit antiproliferative activity. This application is particularly relevant in the development of new cancer treatments.
Used in Anti-Aging Applications:
(Z)-8-DODECEN-1-YL ACETATE is also used as a reagent in the synthesis of disubstituted isoxazoles, which have been shown to exhibit anti-aging activity. This makes it a valuable compound in the cosmetics and skincare industries for the development of anti-aging products.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 675, 1973 DOI: 10.1016/S0040-4039(00)72431-2

Check Digit Verification of cas no

The CAS Registry Mumber 28079-04-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,0,7 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 28079-04:
(7*2)+(6*8)+(5*0)+(4*7)+(3*9)+(2*0)+(1*4)=121
121 % 10 = 1
So 28079-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h5-6H,3-4,7-13H2,1-2H3/b6-5-

28079-04-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name orfralure

1.2 Other means of identification

Product number -
Other names (Z)-8-DODECEN-1-YL ACETATE

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:28079-04-1 SDS

28079-04-1Synthetic route

1-Acetoxydodec-8-yne
26906-26-3

1-Acetoxydodec-8-yne

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With quinoline; hydrogen; Pd-BaSO4 In methanol97%
With hydrogen; Lindlar's catalyst In hexane at 15℃;7 g
(Z)-8-dodecenol
40642-40-8

(Z)-8-dodecenol

acetyl chloride
75-36-5

acetyl chloride

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
In pyridine95%
With pyridine In benzene
Δ8-dodecen-1-ol
153123-34-3

Δ8-dodecen-1-ol

acetic anhydride
108-24-7

acetic anhydride

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With pyridine at 5 - 25℃; for 2h; Large scale;95%
(Z)-8-dodecenol
40642-40-8

(Z)-8-dodecenol

acetic anhydride
108-24-7

acetic anhydride

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 12h; Inert atmosphere; chemoselective reaction;90%
With pyridine89%
In pyridine for 24h; Ambient temperature;75%
(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene
98398-50-6

(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene

acetyl chloride
75-36-5

acetyl chloride

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With acetic acid at 60℃; for 6h;77%
1-penten
109-67-1

1-penten

non-8-en-1-yl acetate
13038-22-7

non-8-en-1-yl acetate

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With C32H41N3O4Ru In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Glovebox; chemoselective reaction;65%
With C35H47N3O4Ru In tetrahydrofuran at 35℃; for 2h;58%
With Z-selective metathesis catalyst
With Z-selective cross-metathesis catalyst Inert atmosphere;
Acetic acid (Z)-6-(toluene-4-sulfonyloxy)-dodec-8-enyl ester

Acetic acid (Z)-6-(toluene-4-sulfonyloxy)-dodec-8-enyl ester

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With sodium tetrahydroborate In dimethyl sulfoxide at 80℃;58%
(E)-8-dodecenyl acetate
38363-29-0

(E)-8-dodecenyl acetate

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
(i) HCl, (ii) NBS, (iii) NaI, DMF; Multistep reaction;
Δ8-dodecen-1-ol
153123-34-3

Δ8-dodecen-1-ol

acetic anhydride
108-24-7

acetic anhydride

A

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

B

(E)-8-dodecenyl acetate
38363-29-0

(E)-8-dodecenyl acetate

Conditions
ConditionsYield
With pyridine Yield given. Yields of byproduct given;
With pyridine at 5 - 25℃; for 2h; Overall yield = 93.3 %; Overall yield = 0.57 kg;A n/a
B n/a
acetic anhydride
108-24-7

acetic anhydride

(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene
98398-50-6

(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
With pyridine; water; toluene-4-sulfonic acid 1) MeOH, room temp., 15 h; 2) room temp., 24 h.; Yield given. Multistep reaction;
n-butyl(triphenyl)phosphonium bromide
1779-51-7

n-butyl(triphenyl)phosphonium bromide

A

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

B

(E)-8-dodecenyl acetate
38363-29-0

(E)-8-dodecenyl acetate

Conditions
ConditionsYield
n-butyl(triphenyl)phosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 18℃; for 2h; Further stages. Title compound not separated from byproducts.;
1-Pentyne
627-19-0

1-Pentyne

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaH / dimethylsulfoxide
2: LiAlH4 / diethyl ether
3: H2 / Lindlar catalyst / methanol
4: Py / benzene
View Scheme
(Z)-oct-4-enal
39924-26-0

(Z)-oct-4-enal

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
2: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
3: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
4: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme
7-chloroheptanoic acid
821-57-8

7-chloroheptanoic acid

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaH / dimethylsulfoxide
2: LiAlH4 / diethyl ether
3: H2 / Lindlar catalyst / methanol
4: Py / benzene
View Scheme
(Z)-4-octene-1-ol
54393-36-1

(Z)-4-octene-1-ol

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
2: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
3: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme
8-Dodecyn-1-ol
41589-71-3

8-Dodecyn-1-ol

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Lindlar catalyst / methanol
2: Py / benzene
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / H2 / Ni-P2
2: 89 percent / pyridine
View Scheme
Multi-step reaction with 2 steps
1: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h
2: pyridine / 15 h / 20 °C
View Scheme
8-Dodecinsaeure
18545-07-8

8-Dodecinsaeure

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4 / diethyl ether
2: H2 / Lindlar catalyst / methanol
3: Py / benzene
View Scheme
1,1-dimethoxy-8-tosyloxy-(4Z)-octene
82861-01-6

1,1-dimethoxy-8-tosyloxy-(4Z)-octene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C
2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature
3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
4: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
5: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
6: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme
1,1-dimethoxy-4Z-octene
119265-28-0

1,1-dimethoxy-4Z-octene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature
2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
3: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
4: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
5: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme
(Z)-1-bromo-4-octene
79837-81-3

(Z)-1-bromo-4-octene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
2: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme
7-bromo-hept-1-ene
4117-09-3

7-bromo-hept-1-ene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide
2: 1) 9-BBN, 2) H2O2, AcONa
3: 85 percent / H2 / Ni-P2
4: 89 percent / pyridine
View Scheme
1-pentynyl lithium
18643-50-0

1-pentynyl lithium

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide
2: 1) 9-BBN, 2) H2O2, AcONa
3: 85 percent / H2 / Ni-P2
4: 89 percent / pyridine
View Scheme
Multi-step reaction with 6 steps
1: 69 percent / Fe acetylacetonate / diethyl ether; liquid ammonia / from -30 to 20 deg C, 15 h
2: 95 percent / pyridine / -5 - 0 °C
3: 90 percent / LiBr / acetone / 6 h / Heating
4: 78 percent / CuI, bi-2-pyridyl / tetrahydrofuran / 2 h / 2 °C
5: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h
6: pyridine / 15 h / 20 °C
View Scheme
Dodec-1-en-8-yne
197901-17-0

Dodec-1-en-8-yne

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) 9-BBN, 2) H2O2, AcONa
2: 85 percent / H2 / Ni-P2
3: 89 percent / pyridine
View Scheme
6-acetoxy-1-hexanal
68750-25-4

6-acetoxy-1-hexanal

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min
2: DMPA / CH2Cl2
3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C
View Scheme
hex-2-enyl-tributylstannane
74940-39-9

hex-2-enyl-tributylstannane

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min
2: DMPA / CH2Cl2
3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C
View Scheme
Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester
156360-24-6

Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: DMPA / CH2Cl2
2: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C
View Scheme
2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran
53963-10-3

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: KO-tBu, n-BuLi / hexane; diethyl ether / -78 deg C up to RT for 17 h
2: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h
3: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature
4: 77 percent / HOAc / 6 h / 60 °C
View Scheme
(Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene
98369-16-5

(Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature
2: 77 percent / HOAc / 6 h / 60 °C
View Scheme
9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene
98369-07-4

9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h
2: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature
3: 77 percent / HOAc / 6 h / 60 °C
View Scheme
methanol
67-56-1

methanol

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

A

Acetic acid 8-methoxy-dodecyl ester

Acetic acid 8-methoxy-dodecyl ester

B

Acetic acid 9-methoxy-dodecyl ester

Acetic acid 9-methoxy-dodecyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

(Z)-8-dodecen-1-yl acetate
28079-04-1

(Z)-8-dodecen-1-yl acetate

Acetic acid 8,9-bis-methylsulfanyl-dodecyl ester
84801-35-4

Acetic acid 8,9-bis-methylsulfanyl-dodecyl ester

Conditions
ConditionsYield
With iodine In diethyl ether; hexane at 40℃;

28079-04-1Downstream Products

28079-04-1Relevant articles and documents

PHEROMONES OF INSECTS AND THEIR ANALOGS. XXI. SYNTHESIS OF ALK-8Z-EN-1-OLS AND THEIR ACETATES FROM A FUNCTIONALLY DIFFERENTIATED PRODUCT OF OZONOLYSIS OF CYCLOOCTENE

Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Tolstikov, G. A.,Panasenko, A. A.

, p. 240 - 243 (1989)

Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) - components of the sex pheromones of many species of Lepidoptera - have been synthesized from cyclooctene (I) in three stages.The ozonolysis of (I) ( -70 deg C, CH2Cl2-MeOH), NaHCO3; -20 deg C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II).The DNPH of (II), (III), mp 59-61 deg C.The coupling of (II) with n-C3H17CH=PPh3 (IV) or with n-C5H11CH=PPh3 (V) (-70 deg C , 2h; 25 deg C, 15h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively.The reduction of (VI) and (VII) gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25 deg C, 24h) of which, (X) and (XI) , were obtained.The yields (percent): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74.The IR and PMR spectra of compounds (II) and (VI-XI) are given.

SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS

-

Paragraph 0261; 0267, (2021/12/28)

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES

-

Paragraph 0156, (2020/02/14)

Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

-

Paragraph 0060; 0067; 0068; 0070; 0076; 0077, (2019/05/21)

The invention provides a synthesis method of a (Z/E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z/E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.

SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS

-

, (2018/09/12)

Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.

A (Z/E) - 8 - dodecene -1 - ethoxylate ester synthesis method

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, (2018/07/06)

The invention discloses a (Z/E)-8-dodecylene-1-olacetate synthesis method. The method is characterized in that 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials undergo a coupling reaction to produce 8-(2-oxotetrahydropyranyl)dodecyne, the 8-(2-oxotetrahydropyranyl)dodecyne is subjected to hydrogenation, one-pot deprotection and esterification so that (Z)-8-dodecylene-1-olacetate and (E)-8-dodecylene-1-olacetate are obtained, wherein a mole ratio of (Z)-8-dodecylene-1-olacetate to (E)-8-dodecylene-1-olacetate is (90%-99.5%): (10%-0.5%). The method utilizes 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials, provides a novel reaction route, has a short route, produces less by-product, has simple and routine processes, is free of complex post-reaction treatment processes and improves production efficiency. The method satisfies different insect pheromone trap or lure requirements on an isomer ratio in practical application and is suitable for large-scale industrial production.

A pheromone food heart insectthe pear is small (Z/E)-8-dodecene acetum acid ester synthetic method

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Paragraph 0046; 0047, (2017/02/28)

The invention provides a synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate. The synthesis method comprises the following steps: (1) by taking methylbenzene or benzene as a solvent and 1,8-octanediol and hydrobromic acid as starting raw materials, performing unilateral bromination reaction to obtain 8-bromooctanol; (2) by taking ethanol as a solvent, adding 8-bromooctanol and triphenylphosphine into a reaction kettle, after the reaction, cooling and separating out 8-hydroxyl octyl triphenylphosphine crystals by taking methylbenzene as an eluent; (3) performing Witting reaction on the 8-hydroxyl octyl triphenylphosphine and n-butyraldehyde under the presence of a catalyst 18-crown ether-6 to obtain (Z/E)-8-dodeceneanol, wherein potassium carbonate is adopted as alkali; and (4) by taking pyridine as a solvent, reacting the (Z/E)-8-dodeceneanol with acetic anhydride or acetyl chloride to obtain (Z/E)-8-dodecene acetate. The method mild in conditions, fewer in steps, high in yield, and suitable for industrial production, and raw materials are easily available.

PALLADIUM-CATALYZED DECARBONYLATION OF FATTY ACID ANHYDRIDES FOR THE PRODUCTION OF LINEAR ALPHA OLEFINS

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Page/Page column, (2014/06/23)

The present invention is directed to methods of forming olefins, especially linear alpha olefins from fatty acids or anhydrides, each method comprising: contacting an amount of precursor carboxylic acid anhydride with a palladium catalyst comprising a bidentate bis-phosphine ligand in a reaction mixture so as to form an olefin in a product with the concomittant formation and removal of CO and water from the reaction mixture, either directly or indirectly, wherein the reaction mixture is maintained with a sub-stoichiometric excess of a sacrificial carboxylic acid anhydride, an organic acid, or both, said sub-stoichiometric excess being relative to the amount of the precursor carboxylic acid anhydride. The precursor carboxylic acid anhydride may be added to the reaction mixture directly or formed in situ by the reaction between at least one precursor carboxylic acid with a stoichiometric amount of the sacrificial acid anhydride.

Palladium-catalyzed decarbonylative dehydration of fatty acids for the production of linear alpha olefins

Liu, Yiyang,Kim, Kelly E.,Herbert, Myles B.,Fedorov, Alexey,Grubbs, Robert H.,Stoltz, Brian M.

, p. 130 - 136 (2014/03/21)

A highly efficient palladium-catalyzed decarbonylative dehydration reaction of carboxylic acids is reported. This method transforms abundant and renewable even-numbered natural fatty acids into valuable and expensive odd-numbered alpha olefins. Additionally, the chemistry displays a high functional group tolerance. The process employs a low loading of palladium catalyst and proceeds under solvent-free and relatively mild conditions.

Concise syntheses of insect pheromones using Z-Selective cross metathesis

Herbert, Myles B.,Marx, Vanessa M.,Pederson, Richard L.,Grubbs, Robert H.

supporting information, p. 310 - 314 (2013/02/23)

Very short synthetic routes to nine cisolefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.

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