8',8',8'-Trifluoroabscisic acid

Base Information

• Chemical Name: 8',8',8'-Trifluoroabscisic acid
• CAS No.: 164457-19-6
• Molecular Formula: C₁₅H₁₇F₃O₄
• Molecular Weight: 318.293
• Mol file: 164457-19-6.mol

Synonyms:8',8',8'-trifluoro-ABA;8',8',8'-trifluoroabscisic acid;8',8',8'-trifluoroabscisic acid, (1alpha,1(2Z,4E),6alpha)-(+-)-isomer;8',8',8'-trifluoroabscisic acid, (1R-(1alpha,1(2Z,4E),6alpha))-isomer;8',8',8'-trifluoroabscisic acid, (1R-(1alpha,1(2Z,4E),6beta))-isomer;8',8',8'-trifluoroabscisic acid, (1S-(1alpha,1(2Z,4E),6alpha))-isomer;8',8',8'-trifluoroabscisic acid, (1S-(1alpha,1(2Z,4E),6beta))-isomer

Chemical Property of 8',8',8'-Trifluoroabscisic acid

Chemical Property:

• Boiling Point: 449oC at 760 mmHg
• Flash Point: 225.3oC
• PSA: 74.60000
• Density: 1.356g/cm3
• LogP: 2.79230
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 318.10789351
• Heavy Atom Count: 22
• Complexity: 586

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CC(C1(C=CC(=CC(=O)O)C)O)(C)C(F)(F)F
• Isomeric SMILES: CC1=CC(=O)C[C@@]([C@]1(/C=C/C(=C/C(=O)O)/C)O)(C)C(F)(F)F

Technology Process of 8',8',8'-Trifluoroabscisic acid

There total 43 articles about 8',8',8'-Trifluoroabscisic acid 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:

4-(1,4-dioxaspiro<4.5>dec-7-en-8-yl)morpholine (54621-20-4) → (2Z,4E)-5-((1S,6S)-1-Hydroxy-2,6-dimethyl-4-oxo-6-trifluoromethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid (164457-19-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: triethylamine; triethylborane

2.1: aq. HCl

5.1: 60 percent / Et₃N

6.1: sodium hydride

7.1: 70 percent / H₂ / 10 percent Pd/C / acetic acid; ethanol / 2585.74 Torr

8.1: LDA

8.2: Et₃N

9.1: bromine

9.2: DBU

10.1: LDA / tetrahydrofuran / 20 °C

11.1: lithium aluminum hydride / tetrahydrofuran / 0 °C

12.1: MnO₂ / acetone / 1 h

13.1: MnO₂; NaCN

14.1: AcOH / 4 h / 20 °C

15.1: TsOH / acetone / 1 h / 20 °C

16.1: NaOH / methanol

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; triethyl borane; sodium cyanide; hydrogen; bromine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; acetone; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Dehydrofluorination / 4.1: Addition / 5.1: Methylation / 6.1: Formylation / 7.1: Hydrogenation / 8.1: Metallation / 8.2: Etherification / 9.1: Bromination / 9.2: Dehydrobromination / 10.1: Addition / 11.1: Reduction / 12.1: Oxidation / 13.1: Oxidation / 14.1: Esterification / 15.1: ketal cleavage / 16.1: Hydrolysis;

DOI:10.1016/S0040-4039(99)01206-X

Reference yield:

4-(1,4-dioxaspiro<4.5>dec-7-en-8-yl)morpholine (54621-20-4) → (2Z,4E)-5-((1R,6S)-1-Hydroxy-2,6-dimethyl-4-oxo-6-trifluoromethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid (164457-19-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: triethylamine; triethylborane

2.1: aq. HCl

5.1: 60 percent / Et₃N

6.1: sodium hydride

7.1: 70 percent / H₂ / 10 percent Pd/C / acetic acid; ethanol / 2585.74 Torr

8.1: LDA

8.2: Et₃N

9.1: bromine

9.2: DBU

10.1: LDA / tetrahydrofuran / 20 °C

11.1: 21 percent / lithium aluminum hydride / tetrahydrofuran / 0 °C

12.1: MnO₂ / acetone / 1 h

13.1: MnO₂; NaCN

14.1: AcOH / 4 h / 20 °C

15.1: TsOH / acetone / 1 h / 20 °C

16.1: NaOH / methanol

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; triethyl borane; sodium cyanide; hydrogen; bromine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; acetone; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Dehydrofluorination / 4.1: Addition / 5.1: Methylation / 6.1: Formylation / 7.1: Hydrogenation / 8.1: Metallation / 8.2: Etherification / 9.1: Bromination / 9.2: Dehydrobromination / 10.1: Addition / 11.1: Reduction / 12.1: Oxidation / 13.1: Oxidation / 14.1: Esterification / 15.1: ketal cleavage / 16.1: Hydrolysis;

DOI:10.1016/S0040-4039(99)01206-X

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (2Z,4E)-5-((1S,6S)-1-Hydroxy-2,6-dimethyl-4-oxo-6-trifluoromethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid (164457-19-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 4A MS / tetrahydrofuran / 48 h

2.1: triethylamine; triethylborane

3.1: aq. HCl

6.1: 60 percent / Et₃N

7.1: sodium hydride

8.1: 70 percent / H₂ / 10 percent Pd/C / acetic acid; ethanol / 2585.74 Torr

9.1: LDA

9.2: Et₃N

10.1: bromine

10.2: DBU

11.1: LDA / tetrahydrofuran / 20 °C

12.1: lithium aluminum hydride / tetrahydrofuran / 0 °C

13.1: MnO₂ / acetone / 1 h

14.1: MnO₂; NaCN

15.1: AcOH / 4 h / 20 °C

16.1: TsOH / acetone / 1 h / 20 °C

17.1: NaOH / methanol

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; triethyl borane; sodium cyanide; hydrogen; bromine; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; acetone; 1.1: Condensation / 2.1: Alkylation / 3.1: Hydrolysis / 4.1: Dehydrofluorination / 5.1: Addition / 6.1: Methylation / 7.1: Formylation / 8.1: Hydrogenation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 10.2: Dehydrobromination / 11.1: Addition / 12.1: Reduction / 13.1: Oxidation / 14.1: Oxidation / 15.1: Esterification / 16.1: ketal cleavage / 17.1: Hydrolysis;

DOI:10.1016/S0040-4039(99)01206-X

upstream raw materials:

cyclohexanedione monoethylene ketal

4-(1,4-dioxaspiro<4.5>dec-7-en-8-yl)morpholine

7-(trifluoromethyl)-1,4-dioxaspiro[4.5]decan-8-one

7-methyl-7-trifluoromethyl-1,4-dioxa-spiro[4.5]decan-8-one

Refernces

• 1、 Todoroki, Yasushi,Hirai, Nobuhiro,Koshimizu, Koichi. "8',8'-DIFLUORO- AND 8',8',8'-TRIFLUOROABSCISIC ACIDS AS HIGHLY POTENT, LONG-LASTING ANALOGUES OF ABSCISIC ACID". . p. 561 - 568. Retrieved 2007/10/02.