Tert-butyl 3-hydroxypent-4-enoate

Base Information

• Chemical Name: Tert-butyl 3-hydroxypent-4-enoate
• CAS No.: 122763-67-1
• Molecular Formula: C9H16O3
• Molecular Weight: 172.22
• Hs Code.: 2918199090
• European Community (EC) Number: 694-530-5
• DSSTox Substance ID: DTXSID90472090
• Nikkaji Number: J1.756.422F
• Mol file: 122763-67-1.mol

Synonyms:Tert-butyl 3-hydroxypent-4-enoate;122763-67-1;4-Pentenoic acid, 3-hydroxy-, 1,1-dimethylethyl ester;MFCD18207180;SCHEMBL622318;DTXSID90472090;Tert-butyl3-hydroxypent-4-enoate;OBFPCKWYDQCBHO-UHFFFAOYSA-N;tert-Butyl 3-Hydroxy-4-pentenoate;AKOS016001383;SS-4562;SY112763;CS-0005933;EN300-260354;A856618

Chemical Property of Tert-butyl 3-hydroxypent-4-enoate

Chemical Property:

• Boiling Point: 238.1±20.0 °C(Predicted)
• PKA: 13.59±0.20(Predicted)
• PSA: 46.53000
• Density: 0.992±0.06 g/cm3(Predicted)
• LogP: 1.26510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl3-Hydroxypent-4-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C=C)O

Technology Process of Tert-butyl 3-hydroxypent-4-enoate

There total 3 articles about Tert-butyl 3-hydroxypent-4-enoate 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: 98.0%

acetic acid tert-butyl ester (540-88-5) + acrolein (107-02-8,25068-14-8) → tert-butyl 3-hydroxypent-4-enoate (122763-67-1)

Guidance literature:

acetic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

acrolein; In tetrahydrofuran; hexane; for 1h; Further stages.;

DOI:10.1021/ol026040k

Reference yield: 92.7%

tert-butyl 2-(2-hydroxy-3,6-dihydro-2H-1,2-oxaborinin-6-yl)acetate (1360458-67-8) + diisopropyl allylboronate (51851-79-7) → tert-butyl 3-hydroxypent-4-enoate (122763-67-1)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 65 ℃; for 18h; Inert atmosphere;

Reference yield: 88.0%

lithium tert-butyl acetate (1207973-75-8) + acrolein (107-02-8,25068-14-8) → tert-butyl 3-hydroxypent-4-enoate (122763-67-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.0833333h;

DOI:10.1016/0040-4039(95)01902-T

upstream raw materials:

acetic acid tert-butyl ester

acrolein

lithium tert-butyl acetate

tert-butyl 2-(2-hydroxy-3,6-dihydro-2H-1,2-oxaborinin-6-yl)acetate

Refernces

• 1、 Thorat, Rakesh G.,Harned, Andrew M.. "Rapid, enantioselective synthesis of the C1-C13 fragment of biselyngbyolide B". . p. 241 - 243. Retrieved 2018.
• 2、 Rabe, Patrick,Klapschinski, Tim A.,Brock, Nelson L.,Citron, Christian A.,D'Alvise, Paul,Gram, Lone,Dickschat, Jeroen S.. "Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid". . p. 1796 - 1801. Retrieved 2014.
• 3、 -. "PROCESS FOR PREPARING PENTENOATE". Page/Page column 11. . Retrieved 2018/09/08.