CAS 1099-45-2|ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate|(Ethoxycarbonylmethylene)triphenylphosphorane|ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate|Ethyl (triphenylphosphoranylidene)acet...

General Information

Structure

Molecular Formula

C₂₂H₂₁O₂P

Molecular Mass

348.374701

Exact Mass

348.12791654

Charge

InChI

InChI=1S/C22H21O2P/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,2H2,1H3

InChIKey

IIHPVYJPDKJYOU-UHFFFAOYSA-N

Canonic Smiles

CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1

Isomeric Smiles

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

6.2381

LogD (pH = 7.4)

6.2381

Log P

6.2381

Molar Refractivity

103.1977

Polarizability

40.616707

Polar Surface Area

26.3

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Names and Identifiers

IUPAC Traditional name

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

Synonyms

(Ethoxycarbonylmethylene)triphenylphosphoraneEthyl (triphenylphosphoranylidene)acetate(Carbethoxymethylene)triphenylphosphoraneEthyl (triphenylphosphoranyliden)acetate(乙氧基羰基亚甲基)三苯基磷烷乙基(三苯基膦)乙酸酯(Ethoxycarbonylmethylene)triphenylphosphoraneTriphenylcarbethoxymethylenephosphorane(2-Ethoxy-2-oxoethylidene)triphenylphosphorane
(Carbethoxymethylene)triphenylphosphorane
(Carbethoxymethylidene)triphenylphosphorane
(Ethoxycarbonylmethylidene)triphenylphosphorane
Ethyl (triphenylphosphoranylidene)acetateethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate乙氧甲酰基亚甲基三苯基膦(Carbethoxymethylene)triphenylphosphorane乙基(三苯基膦)乙酸酯(Ethoxycarbonylmethylene)triphenylphosphorane(乙氧基羰基亚甲基)三苯基磷烷2-(Triphenylphosphoranylidene)acetic Acid Ethyl Ester(Carboethoxymethylene)triphenylphosphorane(2-Ethoxy-2-oxoethylidene)triphenylphosphoraneNSC 72406

IUPAC name

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

Names and Identifiers

Registration numbers

CAS Number

1099-45-2

MDL Number

MFCD00009183

Wikipedia Title

Triphenylcarbethoxymethylenephosphorane

Chemspider ID

PubChem CID

Beilstein Number

EC Number

PubChem SID

2484533616203551624892754

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Triphenylcarbethoxymethylenephosphorane

Sigma Aldrich

C5106

Packaging
25, 100 g in poly bottle
5 g in glass bottle

02595

Application
Stabilized phosphoran

TRC

C175910

A common Wittig reagent. A cholinesterase inhibitor.

Molecule Details

References

PubChem Literature

From Data Sources

• Hata, A., et al.: Mol. Pharmacol., 67, 640 (1996)

• Naito, T., et al.: Chem. Pharm. Bull., 44, 624 (1996)

• More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).

• Coumarins have been synthesized from o-hydroxy acetophenones: Monatsh. Chem., 115, 765 (1984); o-hydroxy aldehydes give the 4-unsubstituted analogues: Chem. Pharm. Bull., 39, 3100 (1991); 42, 2032 (1994); Indian J. Chem. B, 32, 1159 (1993):

• Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).

• See also (Methoxycarbonylmethylene)triphenylphosphorane, A14020, and Appendix 1.

• Stable crystalline ylide which reacts with aldehydes giving substituted ethyl acrylates. This reaction has been used in an indole synthesis from o-nitrobenzaldehydes: Synthesis, 862 (1984); 401 (1987):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

Synonyms

IUPAC name

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

Registration numbers

CAS Number

1099-45-2

MDL Number

MFCD00009183

Wikipedia Title

Triphenylcarbethoxymethylenephosphorane

Chemspider ID

PubChem CID

Beilstein Number

EC Number

PubChem SID

2484533616203551624892754

Molecule Details

Wikipedia

Triphenylcarbethoxymethylenephosphorane

Sigma Aldrich

C5106

Packaging
25, 100 g in poly bottle
5 g in glass bottle

02595

Application
Stabilized phosphoran

TRC

C175910

A common Wittig reagent. A cholinesterase inhibitor.

References

PubChem Literature

From Data Sources

• Hata, A., et al.: Mol. Pharmacol., 67, 640 (1996)

• Naito, T., et al.: Chem. Pharm. Bull., 44, 624 (1996)

• More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).

• Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).

• See also (Methoxycarbonylmethylene)triphenylphosphorane, A14020, and Appendix 1.

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:69791