(2E)-5-(Phenylmethoxy)-2-pentenoic acid

Base Information

• Chemical Name: (2E)-5-(Phenylmethoxy)-2-pentenoic acid
• CAS No.: 128217-54-9
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.241
• DSSTox Substance ID: DTXSID001279997
• Nikkaji Number: J1.645.425G,J1.698.686K
• Mol file: 128217-54-9.mol

Synonyms:SCHEMBL19990182;DTXSID001279997;128217-54-9;(2E)-5-(Phenylmethoxy)-2-pentenoic acid

Chemical Property of (2E)-5-(Phenylmethoxy)-2-pentenoic acid

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCCC=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COCC/C=C/C(=O)O

Technology Process of (2E)-5-(Phenylmethoxy)-2-pentenoic acid

There total 9 articles about (2E)-5-(Phenylmethoxy)-2-pentenoic acid 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: 97.0%

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → 5-benzyloxy-2-(E)-pentenocarboxylic acid (128217-54-9)

Guidance literature:

With lithium hydroxide; In water; acetone; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00444-0

Reference yield: 78.0%

carbon dioxide (124-38-9,18923-20-1) + ((but-3-yn-1-yloxy)methyl)benzene (22273-77-4) + diethylzinc (557-20-0) → 5-benzyloxy-2-(E)-pentenocarboxylic acid (128217-54-9) + (E)-5-benzyloxy-3-ethyl-2-pentenoic acid

Guidance literature:

carbon dioxide; ((but-3-yn-1-yloxy)methyl)benzene; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 1h;

diethylzinc; In tetrahydrofuran; hexane; at 0 ℃; for 2h; Further stages.;

DOI:10.1021/ol016585z

Reference yield: 64.0%

tert-butyl (E)-5-(benzyloxy)pent-2-enoate (149311-00-2) → 5-benzyloxy-2-(E)-pentenocarboxylic acid (128217-54-9)

Guidance literature:

With trifluoroacetic acid; In benzene;

DOI:10.1021/jo00067a015

upstream raw materials:

5-benzyloxy-2(E)-pentenoic acid methyl ester

tert-butyl (E)-5-(benzyloxy)pent-2-enoate

ethyl (2E)-5-(benzyloxy)pent-2-enoate

carbon dioxide

Downstream raw materials:

(4S)-3-((E)-5'-(Benzyloxy)-2'-penetnoyl)-4-(phenylmethyl)-2-oxazolidinone

5-(benzyloxy)pent-2-enoic acid chloride

(S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one

Domitroban

Refernces

• 1、 Pattenden, Gerald,Ashweek, Neil J.,Baker-Glenn, Charles A. G.,Kempson, James,Walker, Gary M.,Yee, James G. K.. "Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation". scheme or table. p. 1478 - 1497. Retrieved 2008/10/09.
• 2、 Chattopadhyay, Shital K.,Pattenden, Gerald. "A total synthesis of the unique tris-oxazole macrolide ulapualide a produced by the marine nudibranch Hexabranchus sanguineus". . p. 2429 - 2454. Retrieved 2007/10/03.