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14369-81-4,MFCD01863567
Catalog No.:AA001I42

14369-81-4 | 2,3-Butadienoic acid, ethyl ester

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1g
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$69.00   $48.00
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5g
95%
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$218.00   $153.00
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10g
95%
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$403.00   $282.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001I42
Chemical Name:
2,3-Butadienoic acid, ethyl ester
CAS Number:
14369-81-4
Molecular Formula:
C6H8O2
Molecular Weight:
112.1265
MDL Number:
MFCD01863567
SMILES:
CCOC(=O)C=C=C
Properties
Properties
 
BP:
80 °C60 mm Hg(lit.)  
Form:
Liquid  
Refractive Index:
n20/D 1.46(lit.)  
Storage:
-20 ℃;Keep in dry area;  

Computed Properties
 
Complexity:
121  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
3  
XLogP3:
0.7  

Downstream Synthesis Route

[1]JournalofOrganicChemistry,1989,vol.54,p.2862-2869

[1]Li,Ridong;Leng,Penglin;Liu,Bin;Wang,Xin;Ge,Zemei;Li,Runtao[Tetrahedron,2016,vol.72,#37,p.5707-5712]

[2]Rout,Laxmidhar;Harned,AndrewM.[Chemistry-AEuropeanJournal,2009,vol.15,#47,p.12926-12928]

[3]Mal,Dipakranjan;Jana,Supriti[JournalofOrganicChemistry,2016,vol.81,#23,p.11857-11865]

[4]An,Feng;Jangra,Harish;Wei,Yin;Shi,Min;Zipse,Hendrik;Ofial,ArminR.[ChemicalCommunications,2022,vol.58,#20,p.3358-3361]

[5]Jung,MichaelE.;Cordova,Jesus;Murakami,Masayuki[OrganicLetters,2009,vol.11,#17,p.3882-3885]

[6]Jung,MichaelE.;Murakami,Masayuki[OrganicLetters,2006,vol.8,#25,p.5857-5859]

[7]Liu,Yunyun;Wang,Hang;Wan,Jie-Ping[JournalofOrganicChemistry,2014,vol.79,#21,p.10599-10604]

[8]Na,Risong;Jing,Chengfeng;Xu,Qihai;Jiang,Hui;Wu,Xi;Shi,Jiayan;Zhong,Jiangchun;Wang,Min;Benitez,Diego;Tkatchouk,Ekaterina;Goddard,WilliamA.;Guo,Hongchao;Kwon,Ohyun[JournaloftheAmericanChemicalSociety,2011,vol.133,#34,p.13337-13348]

[9]Kasten,Kevin;Cordes,DavidB.;Slawin,AlexandraM.Z.;Smith,AndrewD.[EuropeanJournalofOrganicChemistry,2016,vol.2016,#21,p.3619-3624]

[10]Paik,YiHyon;Dowd,Paul[JournalofOrganicChemistry,1986,vol.51,#15,p.2910-2913]

[11]Oh,ChangHo;Gupta,ArunKumar;Park,DaiIn;Kim,Nakjoong[ChemicalCommunications,2005,#45,p.5670-5672]

[12]Huang,Xian;Shen,Ruwei;Zhang,Tiexin[JournalofOrganicChemistry,2007,vol.72,#4,p.1534-1537]

[13]Huang,Zhusheng;Yang,Xiuqin;Yang,Fulai;Lu,Tao;Zhou,Qingfa[OrganicLetters,2017,vol.19,#13,p.3524-3527]

[14]Yao,Chao;Bao,Yishu;Lu,Tao;Zhou,Qingfa[OrganicLetters,2018,vol.20,#8,p.2152-2155]

[15]Li,Sha;Tang,Ziwei;Wang,Yang;Wang,Dan;Wang,Zhanlin;Yu,Chenxia;Li,Tuanjie;Wei,Donghui;Yao,Changsheng[OrganicLetters,2019,vol.21,#5,p.1306-1310]

[16]Liu,Kui;Wang,Gang;Cheng,Shao-Jie;Jiang,Wen-Feng;He,Cheng;Ye,Zhi-Shi[TetrahedronLetters,2019,vol.60,#29,p.1885-1890]

[17]Panchal,Heena;Clarke,Christopher;Bell,Charles;Karad,SomnathNarayan;Lewis,William;Lam,HonWai[ChemicalCommunications,2018,vol.54,#87,p.12389-12392]

[18]Lin,Ling-Zhi;Che,Yuan-Yuan;Bai,Peng-Bo;Feng,Chao[OrganicLetters,2019,vol.21,#18,p.7424-7429]

[19]Zimmermann,Stefan;Akbarzadeh,Mohammad;Otte,Felix;Strohmann,Carsten;Sankar,MuthukumarGomathi;Ziegler,Slava;Pahl,Axel;Sievers,Sonja;Kumar,Kamal[Chemistry-AEuropeanJournal,2019,vol.25,#68,p.15498-15503]

[20]Fei,Weihong;Xu,Ping;Hou,Jie;Yao,Weijun[ChemicalCommunications,2020,vol.56,#78,p.11669-11672]

[21]Liu,Teng;He,Chixian;Wang,Fan;Shen,Xiang;Li,Yongqin;Lang,Man;Li,Guijun;Huang,Chao;Cheng,Feixiang[Synthesis,2021,vol.53,#3,p.518-526]

[22]CurrentPatentAssignee:SUZHOUAIRTOUINTELLIGENTTECH-CN111909148,2020,ALocationinpatent:Paragraph0060;0065-0067;0072;0076-0077;0081;0085-0086

[23]Chen,Yangxu;Li,Tuanjie;Lu,Fangfang;Song,Xue;Yao,Changsheng;Yu,Chenxia;Zhang,Kai[OrganicandBiomolecularChemistry,2022,vol.20,#6,p.1219-1225]

[24]Ametovski,Jhi;Cao,Jing;Hooper,JoelF.;Lupton,DavidW.;Maddigan-Wyatt,JeremyT.[OrganicLetters,2022,vol.24,#15,p.2847-2852]

14369-81-4    113326-75-3    33588-64-6   
1-ethoxycarbonyl-3-(2'-hydroxybenzoyl)-benzob-indolizine 

[1]TetrahedronLetters,1999,vol.40,p.175-176

14369-81-4    603-35-0    10111-08-7   
C24H24O2P(1+)*C4H3N2O(1-) 

[1]Tetrahedron,2006,vol.62,p.3710-3720

14369-81-4   
2-Methoxy-4-(4-methoxy-phenyl)-cyclopent-2-en-(E)-ylidene-aceticacidethylester 

[1]Barluenga,Jose;Vicente,Ruben;Lopez,LuisA.;Tomas,Miguel[JournaloftheAmericanChemicalSociety,2006,vol.128,#21,p.7050-7054]

Literature

Title: DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate.

Journal: Organic & biomolecular chemistry 20121014

Title: Multicomponent reaction to construct spirocyclic oxindoles with a Michael (triple Michael)/cyclization cascade sequence as the key step.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120727

Title: Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Journal: Journal of the American Chemical Society 20110831

Title: Phosphine- and nitrogen-containing Lewis base catalyzed highly regioselective and geometric selective cyclization of isatin derived electron-deficient alkenes with ethyl 2,3-butadienoate.

Journal: Organic letters 20110304

Title: Synthesis of functionalized chromans by PnBu3-catalyzed reactions of salicylaldimines and salicylaldehydes with allenic ester.

Journal: Organic letters 20101217

Title: Phosphine-catalyzed tandem reaction of allenoates with nitroalkenes.

Journal: Organic letters 20101105

Title: Beyond the aza-Morita-Baylis-Hillman reaction: Lewis base-catalyzed reactions of N-Boc-imines with ethyl 2,3-butadienoate.

Journal: The Journal of organic chemistry 20090821

Title: A facile synthetic route to 2 H-chromenes: reconsideration of the mechanism of the DBU-catalyzed reaction between salicylic aldehydes and ethyl 2-methylbuta-2,3-dienoate.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Aza-Baylis-Hillman reactions of N-tosylated aldimines with activated allenes and alkynes in the presence of various Lewis base promoters.

Journal: The Journal of organic chemistry 20051125

Title: Regiocontrolled, palladium-catalyzed bisfunctionalization of allenyl esters. Multicomponent coupling approaches to highly substituted alpha,beta-unsaturated delta-lactones.

Journal: The Journal of organic chemistry 20050819

Title: DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines: synthesis of highly functionalized chromenes.

Journal: Organic letters 20050707

Title: Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one.

Journal: Organic letters 20031127

Title: Highly regioselective construction of spirocycles via phosphine-catalyzed [3 + 2]-cycloaddition.

Journal: The Journal of organic chemistry 20021213

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