(Acetylmethylene)triphenylphosphorane

Base Information

• Chemical Name: (Acetylmethylene)triphenylphosphorane
• CAS No.: 1439-36-7
• Molecular Formula: C21H19OP
• Molecular Weight: 318.355
• Hs Code.: 29319090
• European Community (EC) Number: 215-878-2
• NSC Number: 407394
• DSSTox Substance ID: DTXSID60162572
• Nikkaji Number: J40.756I,J500.731C
• Wikidata: Q72514812
• Mol file: 1439-36-7.mol

Synonyms:1439-36-7;(Acetylmethylene)triphenylphosphorane;1-(Triphenylphosphoranylidene)propan-2-one;1-(Triphenylphosphoranylidene)-2-propanone;1-(Triphenylphosphoranylidene)acetone;2-Propanone, 1-(triphenylphosphoranylidene)-;(Acetonylidenetriphenyl)phosphorane;(Acetylmethylene)triphenylphosphine;(Triphenylacetylmethylene)phosphorane;1-TRIPHENYLPHOSPHORANYLIDENE-2-PROPANONE;2-Propanone, (triphenylphosphoranylidene)-;Triphenylphosphoranylidene-2-propanone;NSC 407394;C21H19OP;1-(triphenyl-lambda5-phosphanylidene)propan-2-one;AI3-63066;Acetylmethylene-triphenylphosphorane;EINECS 215-878-2;2-PROPANONE, TRIPHENYLPHOSPHORANYLIDENE-;MFCD00008774;BRN 0750077;Acetylmethylenetriphenylphosphorane;(2-Oxopropylidene)triphenylphosphorane;(Triphenylphosphoranylidene)-2-propanone;Phosphonium, acetonyltriphenyl-;1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one;(Methylcarbonylmethylene)triphenylphosphorane;SCHEMBL1508;Acetonyltriphenylphosphonium-;WLN: 1V1UPR&R&R;acetonylidenetriphenylphosphorane;triphenylphosphoranylideneacetone;1-(Triphenylphosphoranyl)acetone;acetonylidene-triphenylphosphorane;DTXSID60162572;acetylmethylene triphenylphosphorane;2-oxopropylidenetriphenylphosphorane;acetylmethylidene triphenylphosphoran;AMY25572;C21-H19-O-P;STR03989;triphenylphosphoranyliden-2-propanone;NSC407394;Phosphonium, (2-oxopropyl)triphenyl-;2-oxo-1-propylidenetriphenylphosphoran;AKOS002528407;NSC-407394;1-(Triphenylphosphanylidene)propan-2-one;methylcarbonylmethylenetriphenylphosphorane;1-triphenylphosphoran-ylidene-2-propanone;BP-12292;SY007889;methylcarbonylmethylenetriphenyl phosphorane;1-(Triphenylphosphonio)-2-oxopropan-1-ide;LS-123208;CS-0041020;FT-0604856;1-(Triphenyl-5-phosphanylidene)-propan-2-one;EN300-102571;Methyl (triphenylphosphoranylidene)methyl ketone;1-(Triphenylphosphoranylidene)-2-propanone, 99%;A808140;2-Propanone, 1-(triphenylphosphoranylidene)- (8CI);acetonyl(triphenyl)phosphonium

Chemical Property of (Acetylmethylene)triphenylphosphorane

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 2.56E-09mmHg at 25°C
• Melting Point: 203-205 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 478.5°Cat760mmHg
• Flash Point: 243.2°C
• PSA: 26.88000
• Density: 1.14g/cm³
• LogP: 3.37170
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: Soluble in chloroform. Slightly soluble in methanol.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 318.117352223
• Heavy Atom Count: 23
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

(Acetylmethylene)triphenylphosphorane ^*data from reagent suppliers

Safty Information:

• Statements: 22-36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Wittig Reagent (Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.

Technology Process of (Acetylmethylene)triphenylphosphorane

There total 32 articles about (Acetylmethylene)triphenylphosphorane 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: 98.3%

acetonyltriphenylphosphonium chloride (1235-21-8) → 1-triphenylphosphoranylidene-2-propanone (1439-36-7)

Guidance literature:

With sodium hydroxide;

Reference yield: 96.0%

chloroacetone (78-95-5) + triphenylphosphine (603-35-0) → 1-triphenylphosphoranylidene-2-propanone (1439-36-7)

Guidance literature:

chloroacetone; triphenylphosphine; In acetonitrile; at 100 ℃; Inert atmosphere;

With sodium carbonate; potassium carbonate; In water; acetonitrile;

DOI:10.1002/chem.201403880

Reference yield: 95.0%

acetylmethyltriphenylphosphonium iodide (65602-18-8) → 1-triphenylphosphoranylidene-2-propanone (1439-36-7)

Guidance literature:

With sodium methylate; In methanol; for 0.0833333h;

DOI:10.1055/s-1981-29497

upstream raw materials:

[(acetyl)(phenylcarbamoyl)methylene]triphenylphosphorane

acetylmethyltriphenylphosphonium iodide

(trimethylsilyl)methylenetriphenylphosphorane

acetic anhydride

Downstream raw materials:

5,5,5-trifluoro-4-(trifluoromethyl)penta-3-ene-2-one

(E)-4-pyridin-3-ylbut-3-en-2-one

(E)-5-phenyl-3-penten-2-one

4-Acetyl-3-methoxy-1,5-diphenyl-1H-pyrrole-2-carboxylic acid methyl ester

Refernces

The Cinchona alkaloids: A silicon-directed synthesis of some advanced intermediates

10.1021/jo00015a036

The research focuses on the synthesis of advanced intermediates of Cinchona alkaloids using silicon-directed reactions. The purpose of the study is to develop a more efficient and scalable synthetic route for these alkaloids, which are historically significant therapeutic agents, particularly quinine and quinidine. The key chemicals used in the research include benzylamine, 2-(2-bromoethyl)-1,3-dioxolane, 3-(trimethylsilyl)-2(E)-propenoyl chloride, 1-(triphenylphosphoranylidene)-2-propanone, and various other reagents such as lithium aluminum hydride, sodium borohydride, and ceric ammonium nitrate (CAN). The study concludes that a silicon-directed Baeyer-Villager oxidation is an effective method to achieve the desired transformation, yielding N-benzylmeroquinene aldehyde in good yield. The researchers also successfully synthesized alcohols 23a,b and acetates 24a,b, which are advanced intermediates for the Cinchona alkaloids. The research demonstrates the utility of silicon-directed reactions in the synthesis of complex natural products, providing a potentially more accessible route for the production of these valuable compounds.