Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]-

Base Information

• Chemical Name: Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]-
• CAS No.: 87938-77-0
• Molecular Formula: C11H12O3
• Molecular Weight: 192.214
• DSSTox Substance ID: DTXSID60435617
• Mol file: 87938-77-0.mol

Synonyms:87938-77-0;Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]-;DTXSID60435617

Chemical Property of Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]-

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(O2)C=O

Technology Process of Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]-

There total 8 articles about Oxiranecarboxaldehyde, 3-[(phenylmethoxy)methyl]- 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: 85.0%

cis-4-benzyloxy-2,3-epoxy-1-butanol (87172-27-8) → (±)-3-((benzyloxy)methyl)oxirane-2-carbaldehyde (84573-21-7,87938-77-0,99945-63-8,113215-46-6,114925-54-1,127909-66-4,133321-78-5)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/0040-4039(94)85219-7

Reference yield:

4-benzyloxycrotonaldehyde (69152-87-0) → 3-<(benzyloxy)methyl>oxirane-2-carboxaldehyde (87938-77-0)

Guidance literature:

With (±)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether; dihydrogen peroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1039/b512542a

Reference yield:

4-benzyloxybut-2-enal (69152-87-0,122751-47-7,80885-31-0) → 3-<(benzyloxy)methyl>oxirane-2-carboxaldehyde (87938-77-0)

Guidance literature:

4-benzyloxybut-2-enal; With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; In dichloromethane; at 20 ℃;

With dihydrogen peroxide; In dichloromethane; water; at 20 ℃; for 24h;

DOI:10.1021/ol102164y

upstream raw materials:

cis-4-benzyloxy-2,3-epoxy-1-butanol

(Z)-4-benzyloxy-but-2-en-1-ol

benzyl bromide

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

Downstream raw materials:

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

<2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol

Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate

1-(3-Benzyloxymethyl-oxiranyl)-2-methyl-but-3-en-1-ol

Refernces

• 1、 Deobald, Anna Maria,Corrêa, Arlene G.,Rivera, Daniel G.,Paix?o, Márcio Weber. "Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions". supporting information. p. 7681 - 7684. Retrieved 2013/04/24.
• 2、 Zhao, Gui-Ling,Ibrahem, Ismail,Sunden, Henrik,Cordova, Armando. "Amine-catalyzed asymmetric epoxidation of α,β-unsaturated aldehydes". . p. 1210 - 1224. Retrieved 2008/09/17.