Benzyl buta-2,3-dienoate

Base Information

• Chemical Name: Benzyl buta-2,3-dienoate
• CAS No.: 187661-86-5
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• DSSTox Substance ID: DTXSID90479827
• Nikkaji Number: J1.840.124J
• Mol file: 187661-86-5.mol

Synonyms:Benzyl buta-2,3-dienoate;187661-86-5;starbld0002725;SCHEMBL20109322;Benzyl 2,3-butadienoate, 95%;DTXSID90479827

Chemical Property of Benzyl buta-2,3-dienoate

Chemical Property:

• Refractive Index: n20/D1.545
• Flash Point: >110℃
• PSA: 26.30000
• Density: 1.059 g/mL at 25 °C
• LogP: 2.07090
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 208

Purity/Quality:

BENZYL 2,3-BUTADIENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=CC(=O)OCC1=CC=CC=C1

Technology Process of Benzyl buta-2,3-dienoate

There total 10 articles about Benzyl buta-2,3-dienoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(carbobenzyloxymethylene)triphenylphosphorane (15097-38-8) + acetyl chloride (75-36-5) → buta-2,3-dienoic acid benzyl ester (187661-86-5)

Guidance literature:

With triethylamine; In dichloromethane; Inert atmosphere;

DOI:10.1002/chem.200902208

Reference yield: 87.0%

(E)-benzyl 3-(trifluoromethylsulfonyloxy)but-2-enoate (1313532-88-5) → buta-2,3-dienoic acid benzyl ester (187661-86-5)

Guidance literature:

With triisopropyl phosphite; N-ethyl-N,N-diisopropylamine; In Isopropyl acetate; at 50 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b02736

Reference yield: 83.0%

acetyl chloride (75-36-5) + Benzyl bromoacetate (5437-45-6) → buta-2,3-dienoic acid benzyl ester (187661-86-5)

Guidance literature:

Benzyl bromoacetate; With triphenylphosphine; In ethyl acetate; at 25 ℃; for 8h;

acetyl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1021/acs.joc.1c02940

upstream raw materials:

(carbobenzyloxymethylene)triphenylphosphorane

acetyl chloride

Ketene

Benzyl bromoacetate

Downstream raw materials:

benzyl 2-(hydroxymethyl)buta-2,3-dienoate

Refernces

Diastereoselective aza-baylis-hillman reactions: synthesis of chiral α-allenlamines and 2-azetines from allenie esters

10.1002/ejoc.200901415

The study focuses on the diastereoselective aza-Baylis–Hillman reactions of allenic esters with activated N-sulfonylimines, using DABCO as a catalyst, to synthesize chiral α-allenylamines and 2-azetines. The research explores the reactivity of allenic esters with various N-arylidenebenzenesulfonamides, leading to the formation of optically active products. It was found that the reaction's outcome could be controlled by adjusting the reaction conditions or the electronic properties of the imine reactants. The study also discusses the potential of these synthesized chiral α-allenylamines as building blocks for the synthesis of chiral pyrrolines and pyrroles, as well as the unique reactivity of strained cyclic enamines like 2-azetines. The results include the synthesis of both acyclic and cyclic derivatives, highlighting the versatility of the methodology for constructing molecular frameworks and the generation of functional groups, which aligns with atom economy principles.