4-Tetrahydropyranyloxy-2-butenal

Base Information

• Chemical Name: 4-Tetrahydropyranyloxy-2-butenal
• CAS No.: 57323-08-7
• Molecular Formula: C9H14 O3
• Molecular Weight: 170.21
• DSSTox Substance ID: DTXSID301239392
• Mol file: 57323-08-7.mol

Synonyms:4-tetrahydropyranyloxy-2-butenal;TGPOB

Chemical Property of 4-Tetrahydropyranyloxy-2-butenal

Chemical Property:

• Vapor Pressure: 0.000965mmHg at 25°C
• Boiling Point: 302.9°Cat760mmHg
• Flash Point: 127.9°C
• PSA: 35.53000
• Density: 1.04g/cm³
• LogP: 1.28470
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 154

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)OCC=CC=O
• Isomeric SMILES: C1CCOC(C1)OC/C=C/C=O

Technology Process of 4-Tetrahydropyranyloxy-2-butenal

There total 7 articles about 4-Tetrahydropyranyloxy-2-butenal 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: 74.0%

(E)-4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-en-1-ol (77741-47-0) → 2-<(2-Buten-4-al-yl)oxy>-2H-tetrahydropyran (57323-08-7)

Guidance literature:

With manganese(IV) oxide; In acetone; for 60h; Ambient temperature;

Reference yield: 72.0%

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol (57323-06-5) → 2-<(2-Buten-4-al-yl)oxy>-2H-tetrahydropyran (57323-08-7)

Guidance literature:

With sodium acetate; quinolinium chlorochromate(VI); In dichloromethane; for 6h; Heating;

Reference yield: 65.0%

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol (57323-06-5) → 2-<(2-Buten-4-al-yl)oxy>-2H-tetrahydropyran (57323-08-7) + (2Z)-4-(tetrahydropyran-2-yloxy)but-2-enal (104226-67-7)

Guidance literature:

With chloro{bis-N,N'-(salicylaldehyde)ethylenediiminato}chromium(III); [bis(acetoxy)iodo]benzene; sodium acetate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol000142y

upstream raw materials:

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

4-(tetrahydro-2H-pyran-2-yl)oxy-2-butenol

(Z)-4-chloro-1-<(tetrahydropyran-2-yl)oxy>but-2-ene

(E)-4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-en-1-ol

Downstream raw materials:

C₁₇H₂₄O₃

(5S,6R)-5-Benzenesulfinyl-2-oxo-6-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,4,5,6-hexahydro-benzofuran-5-carboxylic acid ethyl ester

Ethyl 2-oxo-5-phenylsulfinyl-6-tetrahydropyranyloxy-3a,4,5,6-tetrahydro(3H)benzofuran-5-carboxylate

Trimethyl-[(1S,5S,6R)-6-((E)-3-methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyloxy]-silane

Refernces

• 1、 Goodreid, Jordan D.,Wong, Keith,Leung, Elisa,McCaw, Shannon E.,Gray-Owen, Scott D.,Lough, Alan,Houry, Walid A.,Batey, Robert A.. "Total synthesis and antibacterial testing of the A54556 cyclic acyldepsipeptides isolated from streptomyces hawaiiensis". supporting information. p. 2170 - 2181. Retrieved 2014/12/11.
• 2、 Adam, Waldemar,Hajra, Saumen,Herderich, Markus,Saha-M?ller, Chantu R.. "A highly chemoselective oxidation of alcohols to carbonyl products with iodosobenzene diacetate mediated by chromium(III)(salen) complexes: Synthetic and mechanistic aspects". . p. 2773 - 2776. Retrieved 2007/10/03.