1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide

Base Information

• Chemical Name: 1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide
• CAS No.: 703-03-7
• Molecular Formula: C10H11OP
• Molecular Weight: 178.171
• DSSTox Substance ID: DTXSID00368096
• Nikkaji Number: J1.751.425C,J879.612B
• ChEMBL ID: CHEMBL1256412
• Mol file: 703-03-7.mol

Synonyms:1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide;703-03-7;SCHEMBL221410;CHEMBL1256412;1-phenyl-2-phospholene 1-oxide;DTXSID00368096;HMS1784A20;2-Phospholene, 1-phenyl-, 1-oxide;AKOS030696639;1-Phenyl-2,3-dihydro-1H-phosphole 1-oxide;1-phenyl-2,3-dihydro-1H-1??-phosphol-1-one;2,3-Dihydro-1-phenyl-1H,1H,1H-phosphole-1-one;Z56794961

Chemical Property of 1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 178.054751968
• Heavy Atom Count: 12
• Complexity: 226

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CP(=O)(C=C1)C2=CC=CC=C2

Technology Process of 1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide

There total 8 articles about 1H-Phosphole, 2,3-dihydro-1-phenyl-, 1-oxide 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: 95.0%

1-phenyl-3-phospholene 1-oxide (5186-73-2) → 1-phenyl-2-phospholene-1-oxide (703-03-7)

Guidance literature:

With methanesulfonic acid; at 50 ℃; for 60h; Temperature;

DOI:10.3762/bjoc.16.75

Reference yield: 86.0%

1-phenyl-3-phospholene 1-oxide (5186-73-2) + phenylboronic acid (98-80-6) → (1S,3S)-1,3-diphenylphospholane 1-oxide + 1-phenyl-2-phospholene-1-oxide (703-03-7)

Guidance literature:

With chlorobis(cyclooctene)rhodium(I) dimer; potassium hydroxide; (R)-segphos; In 1,4-dioxane; water; at 80 ℃; for 16h; stereoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/jacs.7b04570

Reference yield: 72.0%

1-phenyl-3-phospholene 1-oxide (5186-73-2) + potassium phenyltrifluoborate → (1S,3S)-1,3-diphenylphospholane 1-oxide + 1-phenyl-2-phospholene-1-oxide (703-03-7)

Guidance literature:

With chlorobis(cyclooctene)rhodium(I) dimer; potassium hydroxide; (R)-segphos; In 1,4-dioxane; water; at 80 ℃; for 16h; stereoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/jacs.7b04570

upstream raw materials:

1-phenyl-3-phospholene 1-oxide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylboronic acid

diallyl(phenyl)phosphine oxide

Downstream raw materials:

6,6-dimethyl-1-oxide-1-phenyloctahydro-1H-phospholo<2,3-d>pyrrolo<1,2-b>isoxazole

(3S*,3aS*,4R_P*,6aS*)-3-methoxycarbonyl-2-methyl-4-phenyl-3,3a,4,5,6,6a-hexahydro-2H-phospholo<2,3-d>isoxazole 4-oxide

(+)-(S)-2,3-dihydro-1-phenyl-1H-phosphole 1-oxide

(R)-(-)-2,3-dihydro-1-phenyl-1H-phosphole oxide

Refernces

• 1、 Lim, Kelvin Meng-Hui,Hayashi, Tamio. "Dynamic Kinetic Resolution in Rhodium-Catalyzed Asymmetric Arylation of Phospholene Oxides". . p. 8122 - 8125. Retrieved 2017/06/28.