CAS 2136-75-6|2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde|(Formylmethylene)triphenylphosphorane|2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde|Formylmethylenetriphenylphosphorane|(Triphenylph...

General Information

Structure

Molecular Formula

C₂₀H₁₇OP

Molecular Mass

304.322141

Exact Mass

304.10170179

Charge

InChI

InChI=1S/C20H17OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

InChIKey

CQCAYWAIRTVXIY-UHFFFAOYSA-N

Canonic Smiles

O=CC=P(c1ccccc1)(c1ccccc1)c1ccccc1

Isomeric Smiles

P(=CC=O)(c1ccccc1)(c1ccccc1)c1ccccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

5.1108

LogD (pH = 7.4)

5.1108

Log P

5.1108

Molar Refractivity

92.7414

Polarizability

36.27359

Polar Surface Area

17.07

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

IUPAC Traditional name

2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde 2-(triphenyl-λ⁵-phosphanylidene)acetaldehyde

Synonyms

(Formylmethylene)triphenylphosphoraneFormylmethylenetriphenylphosphorane(Triphenylphosphoranylidene)acetaldehyde甲酰甲撑基三苯基磷(Formylmethylene)triphenylphosphorane(甲酰亚甲基)三苯基正膦2-(Triphenylphosphoranylidene)-acetaldehyde(Triphenylphosphoranylidene)acetaldehyde(2-Oxoethylidene)triphenylphosphorane(甲酰基亚甲基)三苯基磷烷(Formylmethylene)triphenylphosphorane(Triphenylphosphoranylidene)acetaldehyde

IUPAC name

2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde 2-(triphenyl-λ⁵-phosphanylidene)acetaldehyde

Names and Identifiers

Registration numbers

CAS Number

Beilstein Number

EC Number

MDL Number

PubChem CID

PubChem SID

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

280933

Application
Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.1,2
Packaging
5, 25 g in glass bottle

47720

Other Notes
Wittig reagent for the stereoselective synthesis of Z-α,β-unsaturated aldehydes1

Molecule Details

References

PubChem Literature

From Data Sources

• Wittig reaction followed by reduction with DIBAL-H has been used as a route to allylic alcohols. See, e.g.: J. Org. Chem., 47, 1373 (1982).

• Stable ylide, which undergoes Wittig olefination with aldehydes, but not usually with ketones, to give enals: J. Chem. Soc., 1266 (1961); Angew. Chem. Int. Ed., 14, 486 (1975); Tetrahedron Lett., 3071 (1977). See Appendix 1. Reaction with aldehydes generally gives the thermodynamically more stable (E)-enal. Thus glyoxal gives trans,trans-muconic dialdehyde [(E),(E)-2,4-hexadienal]: Chem. Ber., 107, 710 (1974). The following sequence leads to (Z)-enals: Chem. Ber., 115, 161 (1982):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde 2-(triphenyl-λ⁵-phosphanylidene)acetaldehyde

Synonyms

IUPAC name

2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde 2-(triphenyl-λ⁵-phosphanylidene)acetaldehyde

Registration numbers

CAS Number

Beilstein Number

EC Number

MDL Number

PubChem CID

PubChem SID

Molecule Details

280933

Application
Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.1,2
Packaging
5, 25 g in glass bottle

47720

Other Notes
Wittig reagent for the stereoselective synthesis of Z-α,β-unsaturated aldehydes1

Properties

References

PubChem Literature

From Data Sources

• Wittig reaction followed by reduction with DIBAL-H has been used as a route to allylic alcohols. See, e.g.: J. Org. Chem., 47, 1373 (1982).

Bioactivity

PubChem BioAssay

Molecule

ID:69431