1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid

Base Information

• Chemical Name: 1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid
• CAS No.: 146400-26-2
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.229
• DSSTox Substance ID: DTXSID40576895
• Nikkaji Number: J524.347E
• Mol file: 146400-26-2.mol

Synonyms:146400-26-2;1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid;Cyclopropanecarboxylic acid, 1-amino-2-(hydroxymethyl)-3-phenyl- (9CI);DTXSID40576895;1-Amino-2-(hydroxymethyl)-3-phenylcyclopropanecarboxylic acid;1-Amino-2-(hydroxymethyl)-3-phenylcyclopropanecarboxylicacid

Chemical Property of 1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid

Chemical Property:

• PSA: 83.55000
• LogP: 0.87470
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 263

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(C2(C(=O)O)N)CO

Technology Process of 1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid

There total 6 articles about 1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid 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: 66.0%

1-Amino-6-phenyl-2-oxo-3-oxabicyclo<3.1.0>hexane hydrochloride → (E)-1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid (146400-26-2)

Guidance literature:

With sodium hydroxide; Ambient temperature;

DOI:10.1021/jo00056a020

Reference yield:

Malonic acid tert-butyl ester (E)-3-phenyl-allyl ester → (E)-1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid (146400-26-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / tosyl azide, K₂CO₃ / acetonitrile / Ambient temperature

2: 82 percent / CuI*P(OEt)3 / toluene / 100 - 120 °C / other tert-butyl diazomalonates; stereospecific cyclopropanation

3: 90 percent / trifluoroacetic acid (TFA) / CH₂Cl₂ / 5 h / 0 deg C to room temperature

4: 81 percent / NEt₃, diphenylphosphoryl azide / Heating

5: 96 percent / HCl / dioxane

6: 66 percent / 2.5 M aq. NaOH / Ambient temperature

With hydrogenchloride; sodium hydroxide; 4-toluenesulfonyl azide; diphenylphosphoranyl azide; potassium carbonate; triethylamine; trifluoroacetic acid; triethylphosphite copper(I) iodide complex; In 1,4-dioxane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo00056a020

Reference yield:

Cinnamyl tert-butyl diazomalonate → (E)-1-Amino-2-(hydroxymethyl)-3-phenylcyclopropane-1-carboxylic acid (146400-26-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / CuI*P(OEt)3 / toluene / 100 - 120 °C / other tert-butyl diazomalonates; stereospecific cyclopropanation

2: 90 percent / trifluoroacetic acid (TFA) / CH₂Cl₂ / 5 h / 0 deg C to room temperature

3: 81 percent / NEt₃, diphenylphosphoryl azide / Heating

4: 96 percent / HCl / dioxane

5: 66 percent / 2.5 M aq. NaOH / Ambient temperature

With hydrogenchloride; sodium hydroxide; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid; triethylphosphite copper(I) iodide complex; In 1,4-dioxane; dichloromethane; toluene;

DOI:10.1021/jo00056a020

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