Welcome to LookChem.com Sign In|Join Free

Cas Database

72526-00-2

72526-00-2

Identification

  • Product Name:2-Propenoic acid, (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

  • CAS Number: 72526-00-2

  • EINECS:

  • Molecular Weight:286.414

  • Molecular Formula: C19H26O2

  • HS Code:

  • Mol File:72526-00-2.mol

Synonyms:(-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate;(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl prop-2-enoate;(1R,2S,5R)-5-methyl-2-(2-phenylprop-2-yl)cyclohexyl acrylate;(-)-8-phenylmenthyl dimethyl phosphonoacetate;5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate;2-Propenoic acid,(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester;(+)-8-phenylmenthyl acrylate;Acrylic acid,[5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl] ester;

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

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

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 13 Articles be found

Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: Promising biologically active heterocyclic scaffolds

Bhalla, Aman,Modi, Garima,Bari, Shamsher S.,Kumari, Anu,Berry, Shiwani,Hundal, Geeta

, p. 1160 - 1165 (2017/03/02)

An efficient and operationally simple strategy for the stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactam heterocycles is described. The C-3 functionalized 3-phenyl/benzylsulfonyl-β-lactams 3/3′, 5/5′ has been synthesized via Michael addition using different Michael acceptors on trans-3-phenyl/benzylsulfonyl-β-lactams 2(a–f) using K2CO3as a base and acetonitrile/DMF as solvents. The reaction furnished exclusively cis-β-lactam adducts 3(a–r) using sterically less hindered Michael acceptors. Further, the effect of steric bulk and chiralilty of Michael acceptors was explored to achieve target C-3 functionalized β-lactams 3(s-u)/3′(s-u) and 5(a–c)/5′(a–c). The structural and stereochemical analysis of novel β-lactams were carried out using FT-IR, NMR (1H,13C,1H-1H COSY,1H-13C COSY and13C DEPT-135), elemental analysis (CHNS), mass spectrometry (EIMS and LCMS) in representative cases and single crystal X-ray crystallographic studies (3e). The cis or trans configuration of the Michael acceptor (E) at C-3 was assigned with respect to C4-H.

Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

García-Mera, Xerardo,Alves, Maria J.,Goth, Albertino,Do Vale, Maria Luísa,Rodríguez-Borges, José E.

, p. 2909 - 2919 (2013/04/10)

Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.

The origin of stereoselectivity in cycloaddition reactions promoted by stereoisomers of 8-phenylmenthyl glyoxylate oxime

Sousa, Carlos A.D.,Lima, Carlos F.R.A.C.,Andrade, Mariana,García-Mera, Xerardo,Rodriguez-Borges, José E.

, p. 5048 - 5057 (2013/07/04)

A structural study of three synthesized stereoisomeric oximes, (-)-8-phenylmenthyl glyoxylate oxime (8-PMGO), (+)-8-phenylneomenthyl glyoxylate oxime (8-PnMGO), and (-)-8-phenylisoneomenthyl glyoxylate oxime (8-PinMGO), was performed by means of variable temperature 1H NMR spectroscopy, X-ray crystallography, and ab initio calculations. It was found that in 8-PMGO a conformation where the phenyl and oxime moieties are stacked is significantly favored, whereas in the other stereoisomers this preference was not so evident. The conformational differences found between the isomers were used to rationalize the outcome of the reaction (simultaneous 1,3-cycloaddition and aza-Diels-Alder reaction) between the referred oximes and cyclopentadiene, in which the stereoselectivity was evaluated and found to be nicely reproduced by a simple conformational analysis. The global results indicate that the stereoselectivity of the studied oximes, a bit higher for 8-PMGO, originates from their particular conformational distribution, in which the phenyloxime aromatic interaction plays a decisive role.

Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels-Alder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries

Garcia-Mera, Xerardo,Rodriguez-Borges, Jose E.,Vale, M. Luisa C.,Alves, Maria J.

experimental part, p. 7162 - 7172 (2011/10/05)

The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl, and cyclopentadiene is described. The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation, and X-ray data of appropriated derivatives. Experimental results confirm the highly exo-selectivity for these aza-Diels-Alder reactions, single adducts being obtained from combinations of (8PM)-(R-PEA) and (8PNM)-(S-PEA).

Structure-activity relationship studies optimizing the antiproliferative activity of novel cyclic somatostatin analogues containing a restrained cyclic β-amino acid

Sukopp, Martin,Schwab, Richard,Marinelli, Luciana,Biron, Eric,Heller, Markus,Várkondi, Edit,Pap, ákos,Novellino, Ettore,Kéri, Gy?rgy,Kessler, Horst

, p. 2916 - 2926 (2007/10/03)

The cyclic somatostatin analogue cyclo[Pro1-Phe 2-D-Trp3-Lys4-Thr5-Phe6] (L-363,301) displays high biological activity in inhibiting the release of growth hormone, insulin, and glucagon. According to the sequence of L-363,301, we synthesized a number of cyclic hexa- and pentapeptides containing nonnatural α- and β-amino acids. The N-fluorenylmethoxycarbonyl protected cyclic β-amino acid [1S, 2S, 5R]-2-amino-3,5-dimethyl-2-cyclohex-3-enecarboxylic acid (cβAA), for the replacement of the Phe6-Pro1 moiety of L-363,301, was synthesized in two steps by an enantioselective multicomponent reaction using (-)-8-phenylmenthol as a chiral auxiliary. The resulting peptide cyclo[cβAA1-Tyr2-D-Trp 3-Nle4-Thr(Trt)5] (Trt = triphenylmethyl) shows high antiproliferative effects in an in vitro assay with A431 cancer cells. The same peptide without the Trt group does not reveal any biological activity, whereas L-363,301 and closely related hexapeptides show only minor activity. By comparison of the solution structure of cyclo[cβAA1-Tyr 2-D-Trp3-Nle4-Thr(Trt)5] with the structure of L-363,301, a nearly perfect match of the βII′-turn region with D-Trp in the i + 1 position was observed. The cyclic β-amino acid cβAA is likely needed for the bioactive conformation of the peptide.

Process route upstream and downstream products

Process route

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

acrylic acid
79-10-7

acrylic acid

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 10h;
46%
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 10h;
46%
(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
97%
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;
93%
With triethylamine; In dichloromethane; at -10 - 25 ℃;
91%
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2.2h;
87%
With triethylamine; In diethyl ether; 1.) 0 deg C, 4 h, 2.) 20 deg C, 12 h;
75%
With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;
73%
With triethylamine; In tetrahydrofuran; at 20 ℃;
73%
acryloyl chloride; With dmap; In tetrahydrofuran; at 0 ℃; for 0.25h;
(-)-8-phenylmenthol; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; Further stages.;
43%
With triethylamine; dmap; In dichloromethane; 1.) 0 deg C, 1 h, 2.) RT, overnight;
With dmap; triethylamine; In dichloromethane; at 0 ℃;
With dmap; triethylamine;
With dmap; triethylamine; In dichloromethane; for 3h; Inert atmosphere; Cooling with ice;
Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
88002-15-7

Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 97 percent / 10N KOH / ethanol / 20 h / Heating
2: 75 percent / NEt3 / diethyl ether / 1.) 0 deg C, 4 h, 2.) 20 deg C, 12 h
With potassium hydroxide; triethylamine; In diethyl ether; ethanol;
(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate
1427281-83-1

(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: L-Selectride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
3: triethylamine; dmap
With dmap; lithium aluminium tetrahydride; L-Selectride; triethylamine; In tetrahydrofuran;
(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

acrylic acid
79-10-7

acrylic acid

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 10h;
46%
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 10h;
46%
(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
97%
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;
93%
With triethylamine; In dichloromethane; at -10 - 25 ℃;
91%
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2.2h;
87%
With triethylamine; In diethyl ether; 1.) 0 deg C, 4 h, 2.) 20 deg C, 12 h;
75%
With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;
73%
With triethylamine; In tetrahydrofuran; at 20 ℃;
73%
acryloyl chloride; With dmap; In tetrahydrofuran; at 0 ℃; for 0.25h;
(-)-8-phenylmenthol; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; Further stages.;
43%
With triethylamine; dmap; In dichloromethane; 1.) 0 deg C, 1 h, 2.) RT, overnight;
With dmap; triethylamine; In dichloromethane; at 0 ℃;
With dmap; triethylamine;
With dmap; triethylamine; In dichloromethane; for 3h; Inert atmosphere; Cooling with ice;
Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
88002-15-7

Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 97 percent / 10N KOH / ethanol / 20 h / Heating
2: 75 percent / NEt3 / diethyl ether / 1.) 0 deg C, 4 h, 2.) 20 deg C, 12 h
With potassium hydroxide; triethylamine; In diethyl ether; ethanol;
(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate
1427281-83-1

(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: L-Selectride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
3: triethylamine; dmap
With dmap; lithium aluminium tetrahydride; L-Selectride; triethylamine; In tetrahydrofuran;

Global suppliers and manufacturers

Global( 0) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 72526-00-2
Post Buying Request Now
close
Remarks: The blank with*must be completed