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Chemical Structure| 16957-70-3 Chemical Structure| 16957-70-3
Chemical Structure| 16957-70-3

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CAS No.: 16957-70-3

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(E)-2-Methyl-2-pentenoic acid is the component can be used to synthesize the cytotoxic natural product Lactimidomycin[1].

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Product Details of (E)-2-Methyl-2-pentenoic acid

CAS No. :16957-70-3
Formula : C6H10O2
M.W : 114.14
SMILES Code : CC/C=C(C)/C(O)=O
MDL No. :MFCD00002655
InChI Key :JJYWRQLLQAKNAD-SNAWJCMRSA-N
Pubchem ID :5365909

Safety of (E)-2-Methyl-2-pentenoic acid

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:Ⅲ

Application In Synthesis of (E)-2-Methyl-2-pentenoic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 16957-70-3 ]

[ 16957-70-3 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 67-56-1 ]
  • [ 16957-70-3 ]
  • [ 1567-14-2 ]
YieldReaction ConditionsOperation in experiment
91% sulfuric acid; for 16h;Heating / reflux; 2-Methylpent-2-enoic acid methyl ester (16B). A mixture of <strong>[16957-70-3]2-methylpent-2-enoic acid</strong> (5.0 g, 44 mmol) and sulfuric acid (0.5 mL) in methanol (250 mL) was heated at reflux for 16 hours. The solution was allowed to cool down to 20 C and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium hydrogen carbonate (2 x 50 mL), distilled water (50 mL), then with brine (50 mL). The organic layer was dried over anhydrous MGS04, filtered and concentrated under reduced pressure to give the title compound (5.1 g, 91percent) as a colourless oil.
  • 2
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  • [ 5145-01-7 ]
  • 3
  • [ 97-61-0 ]
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  • 4
  • [ 14250-96-5 ]
  • [ 16957-70-3 ]
  • 13
  • [ 26184-62-3 ]
  • [ 16957-70-3 ]
  • [ 80510-15-2 ]
  • 14
  • [ 16957-70-3 ]
  • [ 140461-20-7 ]
  • [ 140461-21-8 ]
  • 16
  • [ 16957-70-3 ]
  • [ 83841-91-2 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 2.25h; General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 C. The mixture was allowed to stir for 15 min at 0 C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5% potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90%.
With thionyl chloride; at 20℃; for 20h; Thionyl chloride (14.5 ml, 199 mmol) was added to 2-methyl (2E)-pentenoic acid (15.0 g, 131 mmol) and the mixture was stirred at room temperature for 20 h. Thionyl chloride was evaporated under reduced pressure, and the obtained residue was added dropwise to 28% aqueous NH3 below 0 C and stirred at the same temperature for 2 h. The reaction mixture was extracted with AcOEt. The organic layer was washed with saturated brine, dried over Na2SO4, and then evaporated under reduced pressure. The obtained residue was rinsed with n-hexane to give 6b (9.53 g, 64% yield) as a white solid.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h;Inert atmosphere; Reflux; [00110] One equivalent of oxalyl chloride (26.45 g, 208 mmol) was added to a 2 L reaction vessel containing one equivalent of (E)-<strong>[16957-70-3]2-methylpent-2-enoic acid</strong> (23.85 g, 208 mmol) in DCM (500 mL) under a flow of N2. While stirring, five drops of dry DMF were pipetted into the mixture creating effervescence. The reaction was left in a state a reflux for 2 hours. An aliquot was taken after 90 minutes showing that the reaction had gone to completion.tool ii] ?H NMR (COG3): 5 1.08 (t, 3H, J = 7.6 Hz, Meb), 5 1.88 (q, 3H, J = 1.0 Hz, Me3), 5 2.26 (quinq, 2H, J = 7.5, 0,9 Hz, Cl-I2), 5 6.87 (tq, I H, J = 7.4 Hz, 1.3 Hz, vinylic-H)[00112] 13C{?H} NMR (CDGI3): 5 12.57 (Meb), 5 13.23 (Me3), 5 22.93 (CH2), 5 154.23 (Vinylic-H)
References: [1]Helvetica Chimica Acta,1982,vol. 65,p. 1563 - 1575.
[2]Chemistry of Natural Compounds,1985,vol. 21,p. 103 - 105.
    Khimiya Prirodnykh Soedinenii,1985,vol. 21,p. 107 - 110.
[3]Synthetic Communications,1993,vol. 23,p. 143 - 152.
[4]Helvetica Chimica Acta,1987,vol. 70,p. 2201 - 2214.
[5]Journal of Chemical Ecology,1996,vol. 22,p. 673 - 680.
[6]Journal of the American Chemical Society,2003,vol. 125,p. 11796 - 11797.
[7]Journal of the American Chemical Society,2005,vol. 127,p. 2390 - 2391.
[8]Tetrahedron,2005,vol. 61,p. 3419 - 3428.
[9]Organic Letters,2005,vol. 7,p. 2349 - 2352.
[10]Chemistry Letters,2006,vol. 35,p. 358 - 359.
[11]Helvetica Chimica Acta,2006,vol. 89,p. 876 - 883.
[12]Advanced Synthesis and Catalysis,2006,vol. 348,p. 2371 - 2375.
[13]Journal of the American Chemical Society,2008,vol. 130,p. 3633 - 3644.
[14]Tetrahedron,2011,vol. 67,p. 5630 - 5634.
[15]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 1060 - 1075.
[16]Chemistry - A European Journal,2012,vol. 18,p. 13780 - 13786.
[17]Journal of the American Chemical Society,2013,vol. 135,p. 5308 - 5311.
[18]Journal of the American Chemical Society,2014,vol. 136,p. 13194 - 13197.
[19]Angewandte Chemie - International Edition,2015,vol. 54,p. 6288 - 6291.
    Angew. Chem.,2015,vol. 127.
[20]Patent: WO2015/189073,2015,A1 .Location in patent: Paragraph 00110; 00111; 00112.
[21]Chemistry - A European Journal,2017,vol. 23,p. 3577 - 3582.
[22]European Journal of Organic Chemistry,2017,vol. 2017,p. 6067 - 6076.
  • 17
  • [ 16957-70-3 ]
  • [ 134778-14-6 ]
  • [ 107153-77-5 ]
  • 18
  • [ 16957-70-3 ]
  • [ 137283-13-7 ]
  • 20
  • [ 16957-70-3 ]
  • [ 101622-48-4 ]
  • 21
  • [ 16957-70-3 ]
  • (E)-2-Methyl-pent-2-enoyl azide [ No CAS ]
  • 22
  • [ 16957-70-3 ]
  • C6H8O2(2-)*2Li(1+) [ No CAS ]
  • 24
  • [ 84307-86-8 ]
  • [ 16957-70-3 ]
  • 25
  • [ 79140-68-4 ]
  • [ 16957-70-3 ]
  • 26
  • [ 123-38-6 ]
  • [ 598-72-1 ]
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  • 27
  • [ 16957-70-3 ]
  • [ 1972-28-7 ]
  • [ 137283-17-1 ]
  • 28
  • [ 1567-14-2 ]
  • [ 1617-37-4 ]
  • [ 16957-70-3 ]
  • 30
  • [ 16957-70-3 ]
  • [ 1187-82-2 ]
YieldReaction ConditionsOperation in experiment
89% In methanol; EXAMPLE 2 Asymmetric hydrogenation of <strong>[16957-70-3]trans-2-methyl-2-pentenoic acid</strong> In an atmosphere of argon, 14.3 mg (16.8*10-3 mmol) of Ru(OAc)2 [(S)-(-)-OcH-binap] complex and 409 mg (3.58 mmol) of <strong>[16957-70-3]trans-2-methyl-2-pentenoic acid</strong> were dissolved in 18 ml of methanol, and the resulting solution was put into a 100 ml capacity autoclave and stirred at 25° C. for 24 hours under a hydrogen pressure of 1.5 atm. The reaction solution was concentrated under a reduced pressure and then subjected to distillation under a reduced pressure to obtain 370 mg of (S)-2-methylpentanoic acid with a yield of 89percent.
  • 31
  • [ 16957-70-3 ]
  • (2R,3S)-2,3-Dibromo-2-methyl-pentanoic acid [ No CAS ]
  • 32
  • [ 80-59-1 ]
  • [ 74-88-4 ]
  • [ 10276-09-2 ]
  • [ 16957-70-3 ]
 

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