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Chemistry
Organic Building Blocks
Carboxylic Acids
2-Methylbut-3-enoic acid
Chemistry
Organic Building Blocks
Carboxylic Acids

[ CAS No. 53774-20-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 53774-20-2
Chemical Structure| 53774-20-2
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Quality Control of [ 53774-20-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 53774-20-2 ]

Product Details of [ 53774-20-2 ]

CAS No. :53774-20-2 MDL No. :MFCD00042650
Formula : C5H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GQWNPIKWYPQUPI-UHFFFAOYSA-N
M.W :100.12 Pubchem ID :143088
Synonyms :

Calculated chemistry of [ 53774-20-2 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.45
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 0.89
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 0.34
Consensus Log Po/w : 0.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.03
Solubility : 9.39 mg/ml ; 0.0938 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 3.27 mg/ml ; 0.0326 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.06
Solubility : 87.8 mg/ml ; 0.877 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 53774-20-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P390-P403+P235-P405-P406-P501 UN#:3265
Hazard Statements:H227-H290-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 53774-20-2 ]

* 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 [ 53774-20-2 ]

[ 53774-20-2 ] Synthesis Path-Downstream   1~68

  • 1
  • [ 106-98-9 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
Reference： [1]Morton; Holden [Journal of the American Chemical Society, 1947, vol. 69, p. 1677,1679]
  • 2
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 22037-73-6 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium
Reference： [1]Roberts; Young [Journal of the American Chemical Society, 1945, vol. 67, p. 150] Lane; Roberts; Young [Journal of the American Chemical Society, 1944, vol. 66, p. 543]
  • 3
  • [ 107-01-7 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
Reference： [1]Morton; Holden [Journal of the American Chemical Society, 1947, vol. 69, p. 1677,1679]
  • 4
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: (E/Z)-crotyl bromide With lithium chloride; zinc In tetrahydrofuran for 2h; Stage #2: carbon dioxide With hydrogenchloride for 24h;
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;
Stage #1: (E/Z)-crotyl bromide; carbon dioxide With indium; cesium fluoride In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;
Reference： [1]Vellalath, Sreekumar; Romo, Daniel [Israel Journal of Chemistry, 2017, vol. 57, # 3, p. 335 - 339]
[2]Rossi,R.; Ingrosso,G. [Gazzetta Chimica Italiana, 1968, vol. 98, p. 866 - 883]
[3]Miao, Bukeyan; Ma, Shengming [Chemical Communications, 2014, vol. 50, # 25, p. 3285 - 3287]
  • 5
  • [ 563-52-0 ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 2-chloro-3-butene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: carbon dioxide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction;
With magnesium Multistep reaction;
Stage #1: 2-chloro-3-butene With magnesium In tetrahydrofuran Heating; Stage #2: carbon dioxide In tetrahydrofuran at -78 - 10℃; Further stages.;
19 %Spectr. Stage #1: 2-chloro-3-butene; carbon dioxide With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;

Reference： [1]Location in patent: experimental part O'Connor, Patrick D.; Bin Kim; Brimble, Margaret A. [European Journal of Organic Chemistry, 2009, # 26, p. 4405 - 4411]
[2]Rossi,R.; Ingrosso,G. [Gazzetta Chimica Italiana, 1968, vol. 98, p. 866 - 883]
[3]Bloodworth; Curtis; Spencer; Tallant [Tetrahedron, 1993, vol. 49, # 13, p. 2729 - 2750]
[4]Andreana, Peter R; McLellan, Jason S; Chen, Yongchen; Wang, Peng George [Organic letters, 2002, vol. 4, # 22, p. 3875 - 3878]
[5]Miao, Bukeyan; Ma, Shengming [Chemical Communications, 2014, vol. 50, # 25, p. 3285 - 3287]
  • 6
  • [ 53774-20-2 ]
  • [ 4516-90-9 ]
YieldReaction ConditionsOperation in experiment
84% With lithium aluminium tetrahydride
75% With lithium aluminium tetrahydride In diethyl ether Heating;
With lithium aluminium tetrahydride
Reference： [1]Bloodworth; Curtis; Spencer; Tallant [Tetrahedron, 1993, vol. 49, # 13, p. 2729 - 2750]
[2]Grandguillot; Rouessac [Tetrahedron, 1991, vol. 47, # 28, p. 5133 - 5148]
[3]Pearce,G.T. et al. [Journal of Organic Chemistry, 1976, vol. 41, # 17, p. 2797 - 2803]
  • 7
  • [ 53774-20-2 ]
  • [ 24560-24-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
With oxalyl dichloride at 0 - 20℃; for 57h;
With oxalyl dichloride In chloroform at 0 - 20℃; for 3h;
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 1h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;

Reference： [1]Rossi,R.; Ingrosso,G. [Gazzetta Chimica Italiana, 1968, vol. 98, p. 866 - 883]
[2]Rajendra, G.; Miller, Marvin J. [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4471 - 4477]
[3]Yevglevskis, Maksims; Lee, Guat L.; Threadgill, Michael D.; Woodman, Timothy J.; Lloyd, Matthew D. [Chemical Communications, 2014, vol. 50, # 91, p. 14164 - 14166]
[4]Yang, Wu; Wang, Yufeng; Lai, Amy; Clark, Charles G.; Corte, James R.; Fang, Tianan; Gilligan, Paul J.; Jeon, Yoon; Pabbisetty, Kumar B.; Rampulla, Richard A.; Mathur, Arvind; Kaspady, Mahammed; Neithnadka, Premsai Rai; Arumugam, Arunachalam; Raju, Sivashankaran; Rossi, Karen A.; Myers, Joseph E.; Sheriff, Steven; Lou, Zhen; Zheng, Joanna J.; Chacko, Silvi A.; Bozarth, Jeffrey M.; Wu, Yiming; Crain, Earl J.; Wong, Pancras C.; Seiffert, Dietmar A.; Luettgen, Joseph M.; Lam, Patrick Y. S.; Wexler, Ruth R.; Ewing, William R. [Journal of Medicinal Chemistry, 2020, vol. 63, # 13, p. 7226 - 7242]
[5]Chen, Shiru; Cheng, Yingjie; Deng, Guo-Jun; Huang, Huawen; Ji, Xiaochen; Qu, Zhonghua [Advanced Synthesis and Catalysis, 2022, vol. 364, # 9, p. 1573 - 1579]
  • 8
  • [ 53774-20-2 ]
  • [ 59014-11-8 ]
YieldReaction ConditionsOperation in experiment
18.5% With (R)-1-phenyl-ethyl-amine In acetone Inert atmosphere; Reflux; (S)-2-Methyl-3-butenoic acid ((S)-4; Method A) To a stirring solution of (±)-2-methyl-3-butenoic acid ((±)-4, 20.0 g, 0.200 mol) in acetone (200 mL) was added (R)-1-phenylethylamine (24.2 g, 0.200 mol) dropwise. The mixture washeated under reux to dissolve a precipitated salt. After coolingto room temperature, the precipitated salt was ltered. The resultingsalt was puried by recrystallization (1.0 g of salt/4.5 mLof acetone, twice). The obtained salt (9.07 g) was dissolved intodil. HCl (3 ; 90 mL), and the solution was extracted with Et2O.The organic layer was washed with brine, dried (Na2SO4) andconcentrated under reduced pressure to give (S)-4 (3.69 g, 18.5%yield): []D23 = +23.0 (c 1.50, CHCl3); NMR H (300 MHz, CDCl3):1.30 (3H, d, J = 7.2 Hz), 3.19 (1H, quint, J = 7.2 Hz), 5.14 (1H, dt,J = 10.2, 1.2 Hz), 5.18 (1H, dt, J = 17.1, 1.2 Hz), 5.93 (1H, ddd, J = 17.1,10.2, 7.2 Hz), 10.18 (1H, br); NMR C (125 MHz, CDCl3): 16.5, 43.5,116.6, 136.5, 181.2. The enantiomeric purity of (S)-4 was determinedby chiral GC analysis to be 54% e.e. Chiral GC: conditions:column, Chiramix (Tamogami et al. 2001) (0.25mmID × 30mL,0.25 μm df); temperature, 75 °C to 180 °C (0.7 °C/min); carrier N2(0.7 mL/min); tR (S)-4: 31.0 min (77.0%), (R)-4: 32.1 min (23.0%).
With (-)-α-methylbenzylamine
Reference： [1]Masuda, Yui; Ogura, Yusuke; Ohkubo, Yasutaka; Takikawa, Hirosato; Watanabe, Hidenori [Bioscience, Biotechnology and Biochemistry, 2021, vol. 85, # 6, p. 1390 - 1394]
[2]Rossi,R. et al. [Gazzetta Chimica Italiana, 1968, vol. 98, p. 1391 - 1399]
  • 9
  • [ 80-59-1 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
83% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
82.9% With lithium diisopropyl amide In tetrahydrofuran; hexane for 1h; Ambient temperature;
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 24℃; for 1h;
Reference： [1]Combettes, Lorraine E.; Schuler, Marie; Patel, Rakesh; Bonillo, Baltasar; Odell, Barbara; Thompson, Amber L.; Claridge, Tim D. W.; Gouverneur, Véronique [Chemistry - A European Journal, 2012, vol. 18, # 41, p. 13126 - 13132]
[2]Rajendra, G.; Miller, Marvin J. [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4471 - 4477]
[3]Deng, Ruohan; Engle, Keary M.; Fu, Yue; Gao, Yang; Li, Zi-Qi; Liu, Peng; Tran, Van T. [Angewandte Chemie - International Edition, 2020, vol. 59, # 51, p. 23306 - 23312][Angew. Chem., 2020, vol. 132, # 51, p. 23506 - 23512,7]
  • 10
  • [ 53774-20-2 ]
  • [ 16644-98-7 ]
  • (3S,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given;
Reference： [1]Larock, Richard C.; Leuck, David J.; Harrison, L. Wayne [Tetrahedron Letters, 1988, vol. 29, # 49, p. 6399 - 6402]
  • 11
  • [ 53774-20-2 ]
  • [ 3240-34-4 ]
  • dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tetrafluoroboric acid In acetic acid for 1h; Ambient temperature;
Reference： [1]Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Bartoli, Donatella [Tetrahedron, 1990, vol. 46, # 20, p. 7139 - 7150]
  • 12
  • [ 53774-20-2 ]
  • [ 588-72-7 ]
  • (3S,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given;
Reference： [1]Larock, Richard C.; Leuck, David J.; Harrison, L. Wayne [Tetrahedron Letters, 1988, vol. 29, # 49, p. 6399 - 6402]
  • 13
  • [ 53774-20-2 ]
  • 4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With bromine; sodium hydrogencarbonate at 0℃;
Reference： [1]Black, T. Howard; Huang, Jianhua [Tetrahedron Letters, 1993, vol. 34, # 9, p. 1411 - 1412]
  • 14
  • [ 53774-20-2 ]
  • [ 64-19-7 ]
  • cis-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
  • trans-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 37% With ammonium persulfate; trifluorormethanesulfonic acid at 70℃;
Reference： [1]Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco [Tetrahedron, 1993, vol. 49, # 24, p. 5351 - 5358]
  • 15
  • [ 53774-20-2 ]
  • [ 106-99-0 ]
  • (3E,6E)-2-Methyl-octa-3,6-dienoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% at 120℃; for 14h;
Reference： [1]Salerno, Giuseppe; Gigliott, Francesco; Chiusoli, Gian Paolo [Journal of Organometallic Chemistry, 1986, vol. 314, p. 231 - 240]
  • 16
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
70% With isopropylmagnesium bromide In diethyl ether Ambient temperature;
Reference： [1]Sato, Fumie; Iijima, Satoshi; Sato, Masao [Journal of the Chemical Society. Chemical communications, 1981, # 4, p. 180 - 181]
  • 17
  • [ 124-38-9 ]
  • [ 591-97-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With magnesium 1.) -70 deg C, THF; 2.) -70 deg C, 0.5 h, then allowed to warm up to 0 deg C; Yield given. Multistep reaction;
49 %Spectr. Stage #1: carbon dioxide; 1-chloro-2-butene With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction;
Reference： [1]Oppolzer, Wolfgang; Kuendig, Ernest Peter; Bishop, Paul M.; Perret, Celia [Tetrahedron Letters, 1982, vol. 23, # 38, p. 3901 - 3904]
[2]Miao, Bukeyan; Ma, Shengming [Chemical Communications, 2014, vol. 50, # 25, p. 3285 - 3287]
  • 18
  • (E)-1-Bromo-2-butene [ No CAS ]
  • [ 124-38-9 ]
  • [ 1617-32-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1: 28 % Spectr. 2: 72 % Spectr. With tetraethylammonium perchlorate; magnesium In N,N-dimethyl-formamide at -10℃; electrochemical reaction;
Reference： [1]Tokuda, Masao; Kabuki, Takashi; Katoh, Yoshitaka; Suginome, Hiroshi [Tetrahedron Letters, 1995, vol. 36, # 19, p. 3345 - 3348]
  • 19
  • [ 53774-20-2 ]
  • [ 3282-30-2 ]
  • C10H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at -78℃; for 1h;
Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738] Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
  • 20
  • [ 53774-20-2 ]
  • [ 543-27-1 ]
  • C10H16O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 1h;
With 4-methyl-morpholine In tetrahydrofuran for 0.0833333h;
Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738] Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[2]Padwa, Albert; Wang, Qiu [Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3210 - 3220]
  • 21
  • [ 75-77-4 ]
  • [ 53774-20-2 ]
  • (E)-2-Methyl-4-trimethylsilanyl-but-2-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -75℃;
Reference： [1]Moret, Eticnne; Franzini, Livia; Schlosser, Manfred [Chemische Berichte, 1997, vol. 130, # 3, p. 335 - 339]
  • 22
  • [ 53774-20-2 ]
  • [ 22122-36-7 ]
YieldReaction ConditionsOperation in experiment
With bromine; triethylamine 1.) CH2Cl2, 1 h, 2.) CHCl3, reflux, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 42 percent / Br2, NaHCO3 / 0 °C 2: 59 percent / AgNO3 / acetic acid / Heating
Reference： [1]Roehrig, Susanne; Hennig, Lothar; Findeisen, Matthias; Welzel, Peter; Mueller, Dietrich [Tetrahedron, 1998, vol. 54, # 14, p. 3439 - 3456]
[2]Black, T. Howard; Huang, Jianhua [Tetrahedron Letters, 1993, vol. 34, # 9, p. 1411 - 1412]
  • 23
  • [ 80-59-1 ]
  • [ 591-51-5 ]
  • [ 53774-20-2 ]
  • [ 19731-91-0 ]
YieldReaction ConditionsOperation in experiment
43% In tetrahydrofuran at -30℃; for 5h;
Reference： [1]Aurell, Maria Jose; Domingo, Luis Ramon; Mestres, Ramon; Munos, Elena; Zaragoza, Ramon Jose [Tetrahedron, 1999, vol. 55, # 3, p. 815 - 830]
YieldReaction ConditionsOperation in experiment
68% With water In diethyl ether Ambient temperature;
  • 25
  • [ 53774-20-2 ]
  • [ 107-18-6 ]
  • 2-methyl-but-3-enoic acid allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
Reference： [1]Andreana, Peter R; McLellan, Jason S; Chen, Yongchen; Wang, Peng George [Organic letters, 2002, vol. 4, # 22, p. 3875 - 3878]
  • 26
  • [ 53774-20-2 ]
  • [ 513-42-8 ]
  • 2-methyl-but-3-enoic acid 2-methyl-allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
Reference： [1]Andreana, Peter R; McLellan, Jason S; Chen, Yongchen; Wang, Peng George [Organic letters, 2002, vol. 4, # 22, p. 3875 - 3878]
  • 27
  • [ 124-38-9 ]
  • [ 17486-12-3 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
42% With methylaluminum dichloride In hexane at 20℃; for 3h;
Reference： [1]Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro [Chemistry Letters, 2003, vol. 32, # 5, p. 454 - 455]
  • 28
  • [ 124-38-9 ]
  • [ 34584-84-4 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
43% With methylaluminum dichloride In hexane at 20℃; for 3h;
Reference： [1]Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro [Chemistry Letters, 2003, vol. 32, # 5, p. 454 - 455]
  • 29
  • [ 16529-56-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
100 % Chromat. With potassium phosphate buffer; Escherichia coli SS1001 cells In water at 35℃; for 1h;
With water at 35℃; for 1h; Enzymatic reaction; potassium phosphate buffer; 18 EXAMPLE; 18 Hydrolysis of 2-Methyl-3-Butenitrile to 2-Methyl-3-Butenoic acid by E. coli SS1001 Cells A 5.0 mL suspension of 0.500 g (wet cell paste) E. COLI SS1001 cells (ATCC PTA-1177) in 50 mM potassium phosphate buffer (pH 7.0) was added to a mixture of 4.91 mL of 50 mM potassium phosphate buffer (PH 7.0) and 81.8 mg of 2-methyl-3-butenenitrile (101 mM final concentration), and the resulting suspension stirred at 35 C. Samples (0.100 mL) were mixed with 0.900 mL of 60 mM N-ethylacetamide (HPLC external standard) in 1: 1 ACETONITRILE : methanol, the resulting mixture was mixed, centrifuged, and the supernatant analyzed by HPLC for 2-METHYL- 3-butenenitrile and 2-methyl-3-butenoic acid. After 1 H, the conversion of 2-methyl-3-butenenitrile was 100 %, and 2-methyl-3-butenoic acid was the only product produced over the course of the reaction.
Reference： [1]Hann, Eugenia C.; Sigmund, Amy E.; Fager, Susan K.; Cooling, Frederick B.; Gavagan, John E.; Bramucci, Michael G.; Chauhan, Sarita; Payne, Mark S.; DiCosimo, Robert [Tetrahedron, 2004, vol. 60, # 3, p. 577 - 581]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2004/101513, 2004, A2 Location in patent: Page 32-33
  • 30
  • [ 53774-20-2 ]
  • [ 125763-07-7 ]
  • (3R,4R)-4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; diphenyl diselenide In acetonitrile at -30℃; for 5h; Title compound not separated from byproducts;
With bromine; sodium hydrogencarbonate In diethyl ether
Reference： [1]Mellegaard, Shelli R.; Tunge, Jon A. [Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8979 - 8981]
[2]Vellalath, Sreekumar; Romo, Daniel [Israel Journal of Chemistry, 2017, vol. 57, # 3, p. 335 - 339]
  • 31
  • acetic acid 1-ethoxythiocarbonylsulfanyl-3-methyl-butyl ester [ No CAS ]
  • [ 53774-20-2 ]
  • 5-acetoxy-3-ethoxythiocarbonylsulfanyl-2,7-dimethyl-octanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dilauryl peroxide In 1,2-dichloro-ethane Heating;
Reference： [1]Bagal, Sharanjeet K.; Tournier, Lucie; Zard, Samir Z. [Synlett, 2006, # 10, p. 1485 - 1490]
  • 32
  • [ 4894-61-5 ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: trans-but-2-enyl chloride With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Reflux; Stage #2: carbon dioxide With sulfuric acid In tetrahydrofuran at -78℃; for 0.5h;
51% Stage #1: trans-but-2-enyl chloride With magnesium In tetrahydrofuran for 3h; Heating; Stage #2: carbon dioxide In tetrahydrofuran Further stages.;
Reference： [1]Yevglevskis, Maksims; Lee, Guat L.; Threadgill, Michael D.; Woodman, Timothy J.; Lloyd, Matthew D. [Chemical Communications, 2014, vol. 50, # 91, p. 14164 - 14166]
[2]Yang, Sung-Hyun; Caprio, Vittorio [Synlett, 2007, # 8, p. 1219 - 1222]
  • 33
  • [ 53774-20-2 ]
  • [ 100-51-6 ]
  • [ 37526-85-5 ]
YieldReaction ConditionsOperation in experiment
98% With dmap; dicyclohexyl-carbodiimide at 20℃; for 12h;
98% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; 116.116B To a solution of 2-methylbut-3-enoic acid (2 g, 18.98 mmol) in CH2C12 (38.0 ml) was added phenylmethanol (1.966 ml, 18.98 mmol), DCC (3.92 g, 18.98 mmol) and DMAP (0.232 g, 1.898 mmol) (slight exotherm). The reaction was stirred at rt for four hours. The reaction was filtered off solid, rinsed with hexane, concentrated. Purification by normal phase chromatography gave 3.55 g (98%) of 116B as a colorless oil
95% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; 2.1 To a solution of 2-methylbut-3-enoic acid (1.0 g, 9.99 mmol) in dichloromethane (1 mL) was added benzyl alcohol (1.1 g, 9.99 mmol), N,N-dicyclohexylcarbodiimide (2.1 g, 9.99 mmol) and dimethylaminopyridine (122 mg, 1.00 mmol). After stirring at 20 °C for 16 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 5% ethyl acetate in petroleum ether) to afford benzyl 2-methylbut-3-enoate (1.8 g, 95%) as colorless oil.
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Intermediate 13. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the resulting mixture was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was collected and concentrated. The filtrate was then concentrated and subjected to silica gel chromatography to yield the desired product as colorless oil.
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; [00354] Intermediate 17. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the reaction was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was concentrated. The residue was purified by silica gel chromatography to yield the desired product as a colorless oil.
186.2 mg With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;

Reference： [1]Yang, Sung-Hyun; Caprio, Vittorio [Synlett, 2007, # 8, p. 1219 - 1222]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2011/100401, 2011, A1 Location in patent: Page/Page column 248
[3]Current Patent Assignee: TENAYA THERAPEUTICS INC - WO2021/127643, 2021, A1 Location in patent: Paragraph 00233-00234
[4]Location in patent: experimental part Den Hartog, Tim; Macia, Beatriz; Minnaard, Adriaan J.; Feringa, Ben L. [Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 999 - 1013]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22814, 2013, A1 Location in patent: Paragraph 00314
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22818, 2013, A1 Location in patent: Paragraph 00354
[7]Miao, Bukeyan; Ma, Shengming [Chemical Communications, 2014, vol. 50, # 25, p. 3285 - 3287]
  • 34
  • [ 53774-20-2 ]
  • furan-2-yl-(2-methyl-but-3-enoyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
Reference： [1]Padwa, Albert; Wang, Qiu [Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3210 - 3220]
  • 35
  • [ 53774-20-2 ]
  • tert-butyl 4-methyl-3-oxo-10-oxa-2-azatricyclo[5.2.101,5]dec-8-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 96 percent / 12 h / 25 °C
Reference： [1]Padwa, Albert; Wang, Qiu [Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3210 - 3220]
  • 36
  • [ 53774-20-2 ]
  • tert-butyl 4-methyl-3-oxo-10-oxa-2-azatricyclo[5.2.101,5]dec-8-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 12 h / 25 °C
Reference： [1]Padwa, Albert; Wang, Qiu [Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3210 - 3220]
  • 37
  • [ 53774-20-2 ]
  • [ 343268-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 75 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating
Reference： [1]Andreana, Peter R; McLellan, Jason S; Chen, Yongchen; Wang, Peng George [Organic letters, 2002, vol. 4, # 22, p. 3875 - 3878]
  • 38
  • [ 53774-20-2 ]
  • 3-methyl-3,6-dihydro-pyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 83 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating
Reference： [1]Andreana, Peter R; McLellan, Jason S; Chen, Yongchen; Wang, Peng George [Organic letters, 2002, vol. 4, # 22, p. 3875 - 3878]
  • 39
  • [ 53774-20-2 ]
  • (4R,5S,2'R)-3-(2'-methyl-3'-butenoyl)-4-methyl-5-phenyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
[2]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
  • 40
  • [ 53774-20-2 ]
  • (4R,5S,2'S)-3-(2'-methyl-3'-butenoyl)-4-methyl-5-phenyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
[2]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
  • 41
  • [ 53774-20-2 ]
  • (S)-4-Benzyl-3-((R)-2-methyl-but-3-enoyl)-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h

Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
[2]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[3]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[4]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
  • 42
  • [ 53774-20-2 ]
  • (S)-4-Benzyl-3-((S)-2-methyl-but-3-enoyl)-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h

Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
[2]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[3]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[4]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
  • 43
  • [ 53774-20-2 ]
  • [ 184292-93-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h
Reference： [1]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
[2]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 42, p. 13525 - 13530]
[3]Dobarro, Alicia; Velasco, Dolores [Tetrahedron, 1996, vol. 52, # 43, p. 13733 - 13738]
  • 44
  • [ 53774-20-2 ]
  • [ 110080-01-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C
Reference： [1]Rajendra, G.; Miller, Marvin J. [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4471 - 4477]
  • 45
  • [ 53774-20-2 ]
  • [ 110080-02-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C 3: pyridine / tetrahydrofuran / 0.5 h / 0 °C
Reference： [1]Rajendra, G.; Miller, Marvin J. [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4471 - 4477]
  • 46
  • [ 53774-20-2 ]
  • [ 129085-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
Reference： [1]Grandguillot; Rouessac [Tetrahedron, 1991, vol. 47, # 28, p. 5133 - 5148]
  • 47
  • [ 53774-20-2 ]
  • [ 129085-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
Reference： [1]Grandguillot; Rouessac [Tetrahedron, 1991, vol. 47, # 28, p. 5133 - 5148]
  • 48
  • [ 53774-20-2 ]
  • (Z)-2-<2-<2-(p-Methoxyphenoxy)ethyl>-2-methylcyclobutane>propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
Reference： [1]Grandguillot; Rouessac [Tetrahedron, 1991, vol. 47, # 28, p. 5133 - 5148]
  • 49
  • [ 53774-20-2 ]
  • (E)-2-<2-<2-(p-Methoxyphenoxy)ethyl>-2-methylcyclobutane>propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr
Reference： [1]Grandguillot; Rouessac [Tetrahedron, 1991, vol. 47, # 28, p. 5133 - 5148]
  • 50
  • [ 53774-20-2 ]
  • [ 82638-92-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 79 percent / CCl4 / 120 h / 30 °C
Reference： [1]Dondoni, Alessandro [Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3998 - 4000]
  • 51
  • [ 53774-20-2 ]
  • [ 82638-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 24 percent / CCl4 / 35 h / Ambient temperature
Reference： [1]Dondoni, Alessandro [Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3998 - 4000]
  • 52
  • [ 53774-20-2 ]
  • [ 82638-93-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 45 percent / CCl4 / 35 h / Ambient temperature
Reference： [1]Dondoni, Alessandro [Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 3998 - 4000]
  • 53
  • [ 53774-20-2 ]
  • (-)(R)-2-Methyl-1-isopropylamino-butan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: SOCl2 2: diethyl ether 3: LiAlH4 / diethyl ether 4: H2 / Pd-CaCO3 / methanol / 760 Torr
Reference： [1]Rossi,R.; Ingrosso,G. [Gazzetta Chimica Italiana, 1968, vol. 98, p. 866 - 883]
  • 54
  • [ 7204-29-7 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1 2M3BA=2-Methyl-3-butenoic acid 2M3BA=2-Methyl-3-butenoic acid CrX=Mixture of Crotyl acetate, 3-Acetoxybutene-1, 3-Iodobutene-1, cis- and trans-crotyl iodides 3PA=cis+trans-3-pentenoic acid
Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC; KONINKLIJKE DSM N.V. - US6015923, 2000, A
  • 55
  • [ 106-99-0 ]
  • [ 542-28-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
4.1% 1 Example 1 After 1 hour the butadiene (BD) conversion was 78.3%, the yield of cis- and trans-3-pentenoic acid (3PA) was 90.9%, the yield of 2-methyl-3-butenoic acid (2M3BA) was 4.2% and the yield of valerolactone (VL) was 5.0%. After 5 hours the BD conversion was 98.2%, the yield of 3PA was 74%, the yield of 2M3BA was 4.1% and the yield of valerolactone was 15.6%.
Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - US5962732, 1999, A
  • 56
  • [ 1617-32-9 ]
  • [ 106-99-0 ]
  • [ 542-28-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
3.2% 2 Example 2 After 1 hour the butadiene conversion was 52.3% and the 3PA yield was 92.1%, the yield of 2M3BA was 3.2% and the yield of VL was 0.9%.
Reference： [1]Current Patent Assignee: KOCH INDUSTRIES, INC. - US5962732, 1999, A
  • 57
  • [ 53774-20-2 ]
  • [ 762-72-1 ]
  • [ 1432497-06-7 ]
YieldReaction ConditionsOperation in experiment
59% With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In dichloromethane Reflux; Inert atmosphere;
In dichloromethane for 24h; Heating;
Reference： [1]Combettes, Lorraine E.; Schuler, Marie; Patel, Rakesh; Bonillo, Baltasar; Odell, Barbara; Thompson, Amber L.; Claridge, Tim D. W.; Gouverneur, Véronique [Chemistry - A European Journal, 2012, vol. 18, # 41, p. 13126 - 13132]
[2]Tredwell, Matthew; Luft, Jennifer A. R.; Schuler, Marie; Tenza, Kenny; Houk, Kendall N.; Gouverneur, Veronique [Angewandte Chemie - International Edition, 2008, vol. 47, # 2, p. 357 - 360]
  • 58
  • [ 1271-19-8 ]
  • [ 927-77-5 ]
  • [ 106-99-0 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; air; carbon dioxide In diethyl ether Addn. of n-PrMgBr (Et2O) to stirred Et2O suspn. of Cp2TiCl2 and C4H6 (Ar, 0°C) over 5 min, stirring (30 min) at room temp. Bubbling of CO2 through soln. (1 h, room temp.), hydrolysis with aq. HCl, passing of air into react. mixt. for 15 min.; Filtn. gives Cp2TiCl2 in 93% yield recovery. Addn. of aq. NaOH to filtrate, sepn. of org. layer, discarding; extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn.;
Reference： [1]Gao, Yuan; Iijima, Satoshi; Urabe, Hirokazu; Sato, Fumie [Inorganica Chimica Acta, 1994, vol. 222, p. 145 - 154]
  • 59
  • [ 12087-70-6 ]
  • [ 1271-19-8 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 82% With hydrogenchloride; air; carbon dioxide In diethyl ether Passing of gaseous CO2 through Et2O soln. of Ti-compd. (Ar) for 1 h, hydrolysis with aq. HCl and then bubbling of air into react. mixt. for 15 min.; Collecting of pptd. crystals of Cp2TiCl2 by filtn., addn. of aq. NaOH, sepn. of org. layer and discarding. Extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn., (1)H NMR.;
Reference： [1]Gao, Yuan; Iijima, Satoshi; Urabe, Hirokazu; Sato, Fumie [Inorganica Chimica Acta, 1994, vol. 222, p. 145 - 154]
  • 60
  • [ 69079-28-3 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h;
Reference： [1]Location in patent: experimental part Grellepois, Fabienne; Portella, Charles [Synthesis, 2008, # 21, p. 3443 - 3446]
  • 61
  • [ 53774-20-2 ]
  • C5H7FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 0℃; for 2h; Inert atmosphere;
Reference： [1]Location in patent: experimental part O'Connor, Patrick D.; Bin Kim; Brimble, Margaret A. [European Journal of Organic Chemistry, 2009, # 26, p. 4405 - 4411]
  • 62
  • [ 53774-20-2 ]
  • [ 1193511-13-5 ]
  • [ 1193511-19-1 ]
YieldReaction ConditionsOperation in experiment
54% With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux;
Reference： [1]Wilkinson, Susan C.; Lozano, Oscar; Schuler, Marie; Pacheco, Maria C.; Gouverneur, Veronique; Salmon, Roger [Angewandte Chemie - International Edition, 2009, vol. 48, # 38, p. 7083 - 7086][Angewandte Chemie, 2009, vol. 121, # 38, p. 7217 - 7220]
  • 63
  • [ 53774-20-2 ]
  • [ 24400-84-8 ]
  • [ 1193511-17-9 ]
YieldReaction ConditionsOperation in experiment
47% With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux;
Reference： [1]Wilkinson, Susan C.; Lozano, Oscar; Schuler, Marie; Pacheco, Maria C.; Gouverneur, Veronique; Salmon, Roger [Angewandte Chemie - International Edition, 2009, vol. 48, # 38, p. 7083 - 7086][Angewandte Chemie, 2009, vol. 121, # 38, p. 7217 - 7220]
  • 64
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 5204-64-8 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 39h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling;
Reference： [1]Takaya, Jun; Sasano, Kota; Iwasawa, Nobuharu [Organic Letters, 2011, vol. 13, # 7, p. 1698 - 1701]
  • 65
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 5204-64-8 ]
  • [ 53774-20-2 ]
  • [ 13201-46-2 ]
YieldReaction ConditionsOperation in experiment
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In tetrahydrofuran; toluene at 20℃; for 40h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene Cooling;
3% Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 72h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling;
Reference： [1]Takaya, Jun; Sasano, Kota; Iwasawa, Nobuharu [Organic Letters, 2011, vol. 13, # 7, p. 1698 - 1701]
[2]Takaya, Jun; Sasano, Kota; Iwasawa, Nobuharu [Organic Letters, 2011, vol. 13, # 7, p. 1698 - 1701]
  • 66
  • [ 53774-20-2 ]
  • [ 20626-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.5 h / -78 °C 2.1: hydrogenchloride / tetrahydrofuran; water; chloroform / 0 °C / pH 3
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 1.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C
Stage #1: 2-methylbut-3-enoic acid With (<i>S</i>)-1-phenyl-ethylamine In acetone at 80℃; for 0.666667h; Stage #2: With hydrogenchloride In water at 20 - 30℃; for 0.666667h; B.2; B.3 Step 2 : Preparation of (R)-2-methylbut-3-enoic acid (S)-1-phenyl-ethane salt (SM-2-4) Compound SM-2-2 (48g, 48mmol) was dissolved in acetone (100 mL) was added Compound SM-2-3 (67mL, 52mmol), refluxed for 40min 80C , natural cooling after crystallization.After suction filtration, the filter cake was added 50mL of acetone, dissolved by heating, crystallization at room temperature, suction-filtered to give the target molecule SM-2-4 (20.5g, 19%, dr≈2/1).Compound SM-2-4 (22g, 99mmol) was dissolved in 1N hydrochloric acid solution (135mL) was stirred at rt 40min, after-treatment to give SM-2 (9.8g, 98%)
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22814, 2013, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22818, 2013, A1
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116882, 2015, A1
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2016/205482, 2016, A1
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116886, 2015, A1
[6]Current Patent Assignee: SICHUAN KELUN PHARMACEUTICAL COMPANY LIMITED - CN109721613, 2019, A Location in patent: Paragraph 0212; 0213; 0216-0220
[7]Corte, James R.; Pinto, Donald J. P.; Fang, Tianan; Osuna, Honey; Yang, Wu; Wang, Yufeng; Lai, Amy; Clark, Charles G.; Sun, Jung-Hui; Rampulla, Richard; Mathur, Arvind; Kaspady, Mahammed; Neithnadka, Premsai Rai; Li, Yi-Xin Cindy; Rossi, Karen A.; Myers, Joseph E.; Sheriff, Steven; Lou, Zhen; Harper, Timothy W.; Huang, Christine; Zheng, Joanna J.; Bozarth, Jeffrey M.; Wu, Yiming; Wong, Pancras C.; Crain, Earl J.; Seiffert, Dietmar A.; Luettgen, Joseph M.; Lam, Patrick Y. S.; Wexler, Ruth R.; Ewing, William R. [Journal of Medicinal Chemistry, 2020, vol. 63, # 2, p. 784 - 803]
  • 67
  • [ 53774-20-2 ]
  • [ 1422387-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22814, 2013, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22818, 2013, A1
[3]Corte, James R.; Pinto, Donald J. P.; Fang, Tianan; Osuna, Honey; Yang, Wu; Wang, Yufeng; Lai, Amy; Clark, Charles G.; Sun, Jung-Hui; Rampulla, Richard; Mathur, Arvind; Kaspady, Mahammed; Neithnadka, Premsai Rai; Li, Yi-Xin Cindy; Rossi, Karen A.; Myers, Joseph E.; Sheriff, Steven; Lou, Zhen; Harper, Timothy W.; Huang, Christine; Zheng, Joanna J.; Bozarth, Jeffrey M.; Wu, Yiming; Wong, Pancras C.; Crain, Earl J.; Seiffert, Dietmar A.; Luettgen, Joseph M.; Lam, Patrick Y. S.; Wexler, Ruth R.; Ewing, William R. [Journal of Medicinal Chemistry, 2020, vol. 63, # 2, p. 784 - 803]
  • 68
  • [ 53774-20-2 ]
  • [ 1422387-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: hydrogen; palladium 10% on activated carbon / methanol / 20 h / 2585.81 Torr / Inert atmosphere
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere 5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 22 h / 20 °C / 2844.39 Torr
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22814, 2013, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2013/22818, 2013, A1
[3]Corte, James R.; Pinto, Donald J. P.; Fang, Tianan; Osuna, Honey; Yang, Wu; Wang, Yufeng; Lai, Amy; Clark, Charles G.; Sun, Jung-Hui; Rampulla, Richard; Mathur, Arvind; Kaspady, Mahammed; Neithnadka, Premsai Rai; Li, Yi-Xin Cindy; Rossi, Karen A.; Myers, Joseph E.; Sheriff, Steven; Lou, Zhen; Harper, Timothy W.; Huang, Christine; Zheng, Joanna J.; Bozarth, Jeffrey M.; Wu, Yiming; Wong, Pancras C.; Crain, Earl J.; Seiffert, Dietmar A.; Luettgen, Joseph M.; Lam, Patrick Y. S.; Wexler, Ruth R.; Ewing, William R. [Journal of Medicinal Chemistry, 2020, vol. 63, # 2, p. 784 - 803]

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