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Cas Database

100017-31-0

100017-31-0

Identification

  • Product Name:5-Hexen-2-one, 4-methyl-6-phenyl-, (4R,5E)-

  • CAS Number: 100017-31-0

  • EINECS:

  • Molecular Weight:188.269

  • Molecular Formula:C13H16O

  • HS Code:

  • Mol File:100017-31-0.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 4 Articles be found

Stereo- and Regiochemistry in Palladium-Catalyzed Nucleophilic Substitution of Optically Active (E)- and (Z)-Allyl Acetates

Hayashi, Tamio,Yamamoto, Akihiro,Hagihara, Toshiya

, p. 723 - 727 (2007/10/02)

Optically acive (E)- and (Z)-allyl acetates, 3-acetoxy-1-phenyl-1-butene (1) and its regioisomer, 1-acetoxy-1-phenyl-3-butene (2), were allowed to react with sodium dimethyl malonate, sodium acetylacetonate, and sodium methyl acetoacetate in the presence of a palladium catalyst.The reaction of (E)-acetates proceeded with retention of configuration and that of (Z)-acetates proceeded with inversion accompanied by geometrical isomerization from Z to E.The stereochemistry observed in the reaction with phenylzinc bromide was opposite to that with the soft nucleophiles.

Regio- and Enantioselective Copper-Catalyzed 1,4-Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ-Unsaturated Alkyl Ketones

Wu, Xiaoting,Xie, Fang,Ling, Zheng,Tang, Liang,Zhang, Wanbin

supporting information, p. 2510 - 2518 (2016/08/16)

A regio- and enantioselective copper-catalyzed 1,4-conjugate addition of trimethylaluminium to linear δ-aryl-substituted α,β,γ,δ-unsaturated alkyl ketones was developed. A series of γ,δ-unsaturated alkyl ketones were obtained in good yields with high regio- and enantioselectivity (up to 88% ee and 96:4 dr). Expansion of the reaction scope to substrates containing aromatic heterocycles also afforded good yields and enantioselectivities (up to 91% ee) with very high regioselectivities, exclusively providing the single 1,4-products. (Figure presented.).

Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

Cheng, Lei,Li, Ming-Ming,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin

supporting information, p. 11627 - 11630 (2018/09/21)

We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of (R)-flobufen.

Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors

Defieber, Christian,Paquin, Jean-Francois,Serna, Sonia,Carreira, Erick M.

, p. 3873 - 3876 (2007/10/03)

We document a series of investigations that led to new substituted [2.2.2]-diene ligands which display high selectivity in Rh(I)-catalyzed conjugate addition reactions to substrates not previously examined with diene ligands. Moreover, we disclose an unexpected, interesting effect that results from the introduction of a third C=C onto the ligand scaffold (cf. 1).

Process route upstream and downstream products

Process route

trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

trans-3-penten-2-one
3102-33-8

trans-3-penten-2-one

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
ConditionsYield
With potassium hydroxide; R,R,R-5-All-3-iBu-8-MeO-1,8-Me2bicyclo[2.2.2]octa-2,5-diene; Rh(H2C=CH2)2Cl;In1,4-dioxane; water;at 25 ℃; Title compound not separated from byproducts;
ethyl (E)-1-phenylbut-1-en-3-ol
36004-04-3

ethyl (E)-1-phenylbut-1-en-3-ol

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / Et3N, 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 16 h / Ambient temperature
2: 1.) NaH, 2.) bis(μ-chloro)bis(π-allyl)dipalladium, 1,2-bis(diphenylphosphino)ethane (dppe) / 1.) THF, 0 deg C, 2.) THF, reflux, 6 h
3: MeONa / methanol / 16 h / Heating
With dmap; bis(η3-allyl-μ-chloropalladium(II)); sodium methylate; sodium hydride; triethylamine; 1,2-bis-(diphenylphosphino)ethane;Intetrahydrofuran; methanol;
(rac)-(E)-2-acetoxy-4-phenylbut-3-ene
82045-04-3

(rac)-(E)-2-acetoxy-4-phenylbut-3-ene

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH, 2.) bis(μ-chloro)bis(π-allyl)dipalladium, 1,2-bis(diphenylphosphino)ethane (dppe) / 1.) THF, 0 deg C, 2.) THF, reflux, 6 h
2: MeONa / methanol / 16 h / Heating
With bis(η3-allyl-μ-chloropalladium(II)); sodium methylate; sodium hydride; 1,2-bis-(diphenylphosphino)ethane;Inmethanol;
(R)-(Z)-1-hydroxy-1-phenyl-2-butene
100017-30-9

(R)-(Z)-1-hydroxy-1-phenyl-2-butene

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N, 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 16 h / Ambient temperature
2: 1.) NaH, 2.) bis(μ-chloro)bis(π-allyl)dipalladium, 1,2-bis(diphenylphosphino)ethane (dppe) / 1.) THF, 0 deg C, 2.) THF, reflux, 6 h
3: MeONa / methanol / 16 h / Heating
With dmap; bis(η3-allyl-μ-chloropalladium(II)); sodium methylate; sodium hydride; triethylamine; 1,2-bis-(diphenylphosphino)ethane;Intetrahydrofuran; methanol;
(R)-(Z)-1-acetoxy-1-phenyl-2-butene
100017-28-5

(R)-(Z)-1-acetoxy-1-phenyl-2-butene

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH, 2.) bis(μ-chloro)bis(π-allyl)dipalladium, 1,2-bis(diphenylphosphino)ethane (dppe) / 1.) THF, 0 deg C, 2.) THF, reflux, 6 h
2: MeONa / methanol / 16 h / Heating
With bis(η3-allyl-μ-chloropalladium(II)); sodium methylate; sodium hydride; 1,2-bis-(diphenylphosphino)ethane;Inmethanol;
(R)-<1-((E)-styryl)ethyl>acetylacetone
118578-64-6

(R)-<1-((E)-styryl)ethyl>acetylacetone

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
ConditionsYield
With sodium methylate;Inmethanol;for 16h; Yield given. Title compound not separated from byproducts; Heating;
(E)-buta-1,3-dienylbenzene
16939-57-4

(E)-buta-1,3-dienylbenzene

acetone
67-64-1

acetone

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); C72H100O6P2; potassium tert-butylate;Inethanol;at 90 ℃; for 72h; Overall yield = 52 %; enantioselective reaction; Inert atmosphere; Sealed tube;
88 % ee
(E,E)-6-phenyl-3,5-hexadien-2-one
4173-44-8

(E,E)-6-phenyl-3,5-hexadien-2-one

trimethylaluminum
75-24-1

trimethylaluminum

(5E)-6-phenyl-4-hepten-2-one
864148-47-0

(5E)-6-phenyl-4-hepten-2-one

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
ConditionsYield
With C48H50N2O4P2; copper(II) acetate monohydrate;Intetrahydrofuran;at -30 ℃; for 12h; Reagent/catalyst; regioselective reaction; Inert atmosphere;
87 % ee
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 20 - 40 °C
2: copper(II) acetate monohydrate; C48H50N2O4P2 / tetrahydrofuran / 12 h / -30 °C / Inert atmosphere
With C48H50N2O4P2; copper(II) acetate monohydrate; sodium hydroxide;Intetrahydrofuran; water;
trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

trans-3-penten-2-one
3102-33-8

trans-3-penten-2-one

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one
100017-31-0

(4R,5E)-4-methyl-6-phenyl-5-hexaen-2-one

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one
1094836-36-8

(4S,5E)-4-methyl-6-phenyl-5-hexen-2-one

Conditions
ConditionsYield
With potassium hydroxide; R,R,R-5-All-3-iBu-8-MeO-1,8-Me2bicyclo[2.2.2]octa-2,5-diene; Rh(H2C=CH2)2Cl;In1,4-dioxane; water;at 25 ℃; Title compound not separated from byproducts;

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