Cyclopropaneacetamide, 1-(2-propenyloxy)-(9CI)

Base Information

• Chemical Name: Cyclopropaneacetamide, 1-(2-propenyloxy)-(9CI)
• CAS No.: 540133-81-1
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.197
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70447564
• Wikidata: Q82266434
• Mol file: 540133-81-1.mol

Synonyms:540133-81-1;Cyclopropaneacetamide, 1-(2-propenyloxy)- (9CI);DTXSID70447564

Chemical Property of Cyclopropaneacetamide, 1-(2-propenyloxy)-(9CI)

Chemical Property:

• PSA: 53.31000
• LogP: 1.74670
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC1(CC1)CC(=O)N

Technology Process of Cyclopropaneacetamide, 1-(2-propenyloxy)-(9CI)

There total 2 articles about Cyclopropaneacetamide, 1-(2-propenyloxy)-(9CI) 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: 74.0%

2-[1-(allyloxy)cyclopropyl]acetic acid (540133-73-1) → 2-[1-(allyloxy)cyclopropyl]acetamide (540133-81-1)

Guidance literature:

2-[1-(allyloxy)cyclopropyl]acetic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 25 ℃; for 2.5h;

With ammonium acetate; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200390093

Reference yield:

ethyl cyclopropenylideneacetate (74592-36-2) → 2-[1-(allyloxy)cyclopropyl]acetamide (540133-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / NaH / kerosene / 0 °C

2.1: N,N'-carbonydiimidazole / tetrahydrofuran / 2.5 h / 25 °C

2.2: 74 percent / NH₄OAc / tetrahydrofuran / 16 h / 20 °C

With sodium hydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; kerosene;

DOI:10.1002/ejoc.200390093

Reference yield:

2-[1-(allyloxy)cyclopropyl]acetamide (540133-81-1) → 3-[4-amino-5-(1-hydroxycyclopropyl)pyrimidin-2-yl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / trifluoroacetic anhydride / CH₂Cl₂; pyridine / 0 - 20 °C

2.1: potassium hydride / kerosene; tetrahydrofuran / 3 h / 0 - 20 °C

2.2: 92 percent / 18-crown-6 / tetrahydrofuran / 3 h / 20 - 40 °C

3.1: 46 percent / sodium ethoxide / ethanol / 20 h / Heating

4.1: 44 percent / Ti(OiPr)4 / tetrahydrofuran; diethyl ether / 3 h / 10 - 20 °C

With sodium ethanolate; potassium hydride; trifluoroacetic anhydride; titanium(IV) isopropylate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; kerosene;

DOI:10.1002/ejoc.200390093

upstream raw materials:

2-[1-(allyloxy)cyclopropyl]acetic acid

ethyl cyclopropenylideneacetate

Downstream raw materials:

(Z)-3-(4-amino-5-{1-[(1-propenyl)oxy]cyclopropyl}pyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

3-{5-[1-(allyloxy)cyclopropyl]-4-aminopyrimidin-2-yl}-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Refernces