4-Tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one

Base Information

• Chemical Name: 4-Tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one
• CAS No.: 117254-07-6
• Molecular Formula: C16H31 N O2 Si
• Molecular Weight: 297.513
• DSSTox Substance ID: DTXSID10721299
• Mol file: 117254-07-6.mol

Synonyms:SCHEMBL7718743;DTXSID10721299;4-tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one

Chemical Property of 4-Tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one

Chemical Property:

• PSA: 29.54000
• LogP: 3.61780
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 296.204580734
• Heavy Atom Count: 20
• Complexity: 378

Purity/Quality:

97% ^*data from raw suppliers

(R)-2-[(Diethylamino)methyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-cyclopenten-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC1=C(C(CC1=O)C(C)(C)C)O[Si](C)C
• Uses: (R)-2-[(Diethylamino)methyl]-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-cyclopenten-1-one is a prostaglandin DP receptor agonist which may be used as topical antiglaucoma agents.

Technology Process of 4-Tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one

There total 33 articles about 4-Tert-butyl-2-[(diethylamino)methyl]-3-[(dimethylsilyl)oxy]cyclopent-2-en-1-one 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%

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone (117254-03-2) + diethylamine (109-89-7) → (4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6)

Guidance literature:

DOI:10.1021/jo00100a010

Reference yield: 95.0%

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone (117253-98-2) + diethylamine (109-89-7) → (4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6)

Guidance literature:

In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/jo00258a051

Reference yield: 71.3%

diethylamine (109-89-7) + (R)-2-Bromomethyl-4-(tert-butyldimethylsiloxy)cyclopent-2-enone (176446-40-5) → (4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6)

Guidance literature:

With triethylamine; In hexane; at 20 ℃; Inert atmosphere;

upstream raw materials:

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone

diethylamine

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(S)-1-[(R)-oxiran-2-yl]prop-2-enol

Downstream raw materials:

[3R(1E,3R),4R]-3-[3-cyclohexyl-3-[(3-oxapent-1-yl)oxy]propyl]-4-(t-butyldimethylsiloxy)-2-methylenecyclopentanone

3-{3-[(1R,2S,3R)-3-Hydroxy-2-((R)-3-hydroxy-4-phenoxy-but-1-ynyl)-5-oxo-cyclopentyl]-propoxy}-propionic acid methyl ester

7-[(1R,2S,3R)-3-Hydroxy-2-((R)-3-hydroxy-4-phenoxy-but-1-ynyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester

(E)-7-[(1R,2S,3R)-3-Hydroxy-2-((R)-3-hydroxy-4-phenoxy-but-1-ynyl)-5-oxo-cyclopentyl]-hept-2-enoic acid methyl ester

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