CID 6093773

Base Information

• Chemical Name: CID 6093773
• CAS No.: 13291-18-4
• Molecular Formula: C3H5BrMg
• Molecular Weight: 145.282
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID30400519
• Mol file: 13291-18-4.mol

Synonyms:DTXSID30400519;FT-0694868

Chemical Property of CID 6093773

Chemical Property:

• Melting Point: 102-104 °C
• Boiling Point: 67 °C
• Flash Point: -36 °F
• PSA: 0.00000
• Density: 0.94 g/mL at 20 °C
• LogP: 1.91490
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 143.94250
• Heavy Atom Count: 5
• Complexity: 7.5

Purity/Quality:

99%, ^*data from raw suppliers

Isopropenylmagnesium bromide solution 1.0 M in 2-methyltetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C
• Statements: 11-14/15-34-40-37-19-14
• Safety Statements: 26-30-36/37/39-43-45-7/8-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[C-]=C.[Mg+2].[Br-]
• Uses: Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry Isopropenylmagnesium bromide (iPrMgBr) solution (0.5 M in THF) has been used in the Grignard reaction, a key step the in preparation of zofenoprilat and (S)-(?)-phosphonotrixin. It can also be used for the regioselective ring opening of an optically active epoxy alcohol in the total synthesis of (+)-desepoxyasperdiol.

Technology Process of CID 6093773

There total 2 articles about CID 6093773 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:

2-bromoprop-1-ene (557-93-7) → isopropenylmagnesium bromide (13291-18-4)

Guidance literature:

With magnesium; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo951806y

Reference yield:

→ isopropenylmagnesium bromide (13291-18-4)

Guidance literature:

Reference yield: 85.0%

cyclohept-1-en-1-yl trifluoromethanesulfonate (28075-51-6) + carbon monoxide (201230-82-2) + isopropenylmagnesium bromide (13291-18-4) → C11H16O (1030239-96-3) + 2,3-dimethyl-buta-1,3-diene (513-81-5)

Guidance literature:

isopropenylmagnesium bromide; With zinc dibromide; In tetrahydrofuran; at 20 ℃;

cyclohept-1-en-1-yl trifluoromethanesulfonate; carbon monoxide; With zinc dibromide; nickel dichloride; In tetrahydrofuran; dimethyl sulfoxide; at 50 ℃; for 0.333333h; under 760.051 Torr; Further stages.;

DOI:10.1016/j.tetlet.2008.03.035

upstream raw materials:

2-bromoprop-1-ene

Downstream raw materials:

1-chloro-4-(1-methylethenyl)-benzene

3-(1-propen-2-yl)cyclohexanone

1,4-Dichlor-2,5-di-isopropenyl-benzol

3,5-Di-isopropenyl-1-chlorbenzol

Refernces

Copper-catalyzed asymmetric conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes

10.1016/j.tetasy.2009.06.001

The research investigates the copper-catalyzed asymmetric conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes, aiming to produce 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-2-branched alkanes with enantioenrichment. The study screens various copper ligands, finding that certain Josiphos ligands provide low to moderate enantioselectivity and good diastereoselectivity when using allylmagnesium bromide. The stereochemistry of the products is assigned by comparing them with those synthesized via chiral pool synthesis and stereoselective lithiation methods. The research concludes that most typical copper ligands slow down the addition reaction, and substrate 5b with allylmagnesium bromide shows the best enantioselectivity. Key chemicals used include 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes as substrates, Grignard reagents like isopropenylmagnesium bromide and allylmagnesium bromide, and various copper ligands such as Josiphos and NHC ligands.

Formation of highly substituted chiral cyclohexanone derivatives using a tandem conjugate addition/cyclisation

10.1016/j.tetlet.2004.09.150

The study presents a tandem conjugate addition/cyclisation approach for synthesizing chiral, highly substituted cyclohexanone and cyclohexenone derivatives. This method is significant for its potential application in the synthesis of natural products, particularly those from the Tridachia family of marine molluscs. The researchers used an Evans' chiral auxiliary to control the formation of the six-membered ring as a single enantiomer. The auxiliary also controlled the aldol reaction, generating stereocenters in the acyclic precursor. The study involved the use of dimethylcopperlithium and a cuprate derived from isopropenylmagnesium bromide to perform the addition-cyclisation. The enoate 11 and enone 12 were used as substrates, and the resulting cyclic products 22-24 were further functionalized through methylation and β-elimination to yield enones 25-27. The study demonstrated the viability of this strategy for creating complex cyclohexanone derivatives with high stereocontrol, which could be useful in the synthesis of natural products like tridachiahydropyrone, 9,10-deoxytridachione, and tridachiapyrone-A.

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