22255-17-0

Basic information

• Product Name: (alpha-carboxycyclopropyl)glycine
• Synonyms: (alpha-carboxycyclopropyl)glycine
• CAS NO: 22255-17-0
• Molecular Formula: C6H9 N O4
• Molecular Weight: 0
• Mol File: 22255-17-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 414.1°Cat760mmHg
• Flash Point: 204.3°C
• Appearance: /
• Density: 1.601g/cm³
• Vapor Pressure: 5.11E-08mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (alpha-carboxycyclopropyl)glycine(CAS DataBase Reference)
• NIST Chemistry Reference: (alpha-carboxycyclopropyl)glycine(22255-17-0)
• EPA Substance Registry System: (alpha-carboxycyclopropyl)glycine(22255-17-0)

Safety Data

• Hazardous Substances Data: 22255-17-0(Hazardous Substances Data)

Usage

Description

(alpha-carboxycyclopropyl)glycine, also known as ACCG, is a chemical compound characterized by the presence of a cyclopropyl ring and a carboxylic acid group attached to a glycine molecule. It is recognized for its unique structure and properties, which make it a valuable tool in medicinal chemistry research. ACCG is commonly utilized as a building block in the synthesis of biologically active compounds and has been investigated for its potential pharmaceutical applications, particularly in the development of new drugs for the treatment of various diseases.

Uses

Used in Pharmaceutical Research:
(alpha-carboxycyclopropyl)glycine is used as a building block for the synthesis of biologically active compounds due to its unique structure and properties. It plays a crucial role in the development of new drugs for the treatment of various diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (alpha-carboxycyclopropyl)glycine is used as a valuable tool for research and development. Its specific functions and potential uses in medicine are still being explored, making it a promising candidate for future pharmaceutical applications.
Note: Since the provided materials do not specify different applications in various industries, the uses are generalized based on the information given. If more specific applications are available, they can be listed separately following the format provided in the example.

InChI:InChI=1/C6H9NO4/c7-4(6(10)11)2-1-3(2)5(8)9/h2-4H,1,7H2,(H,8,9)(H,10,11)

Upstream product

• 90035-39-5 (1R,2R)-2-(Amino-cyano-methyl)-cyclopropanecarboxylic acid amide 
• 90035-37-3 (+/-)-trans-2-(cyanohydroxymethyl)cyclopropane-1-carboxylate 
• 87986-39-8 ethyl trans-2-(diethoxymethyl)cyclopropane-1-carboxylate 
• 13949-93-4 (+/-)-ethyl trans-2-formyl-1-cyclopropanecarboxylate 
• 151-50-8 potassium cyanide 
• 121704-23-2 2-[Carboxy-(2-methoxy-acetylamino)-methyl]-cyclopropanecarboxylic acid 
• 95605-08-6 (R)-tert-Butoxycarbonylamino-((1R,2S)-2-hydroxymethyl-cyclopropyl)-acetic acid methyl ester 
• 104682-00-0 (1R,2S)-2-((S)-tert-Butoxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid 
• 117747-67-8 (1R,2S)-2-((S)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid 
• 129397-30-4 (1R,2R)-2-((S)-tert-Butoxycarbonyl-dibenzylamino-methyl)-cyclopropanecarboxylic acid tert-butyl ester 
• 128134-29-2 2-((R)-Benzyloxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid ethyl ester 
• 22255-17-0 2-((R)-Amino-carboxy-methyl)-cyclopropanecarboxylic acid 
• 128134-30-5 (R)-4-(2-Carboxy-cyclopropyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 124085-73-0 2-[(R)-1-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarboxylic acid ethyl ester 

Downstream Products

• 22255-17-0 (2R,3R,4R) α-(Carboxycyclopropyl)glycine 
• 22255-17-0 (2R,3S,4S) α-(Carboxycyclopropyl)glycine 
• 128134-31-6 (R)-4-[(R)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 128134-31-6 (R)-4-[(S)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 128134-30-5 (R)-4-(2-Carboxy-cyclopropyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

Reactivity of (Bicyclo[5.1.0]octadienyl)iron(1+) Cations: Application to the Synthesis of cis-2-(2′-Carboxycyclopropyl)glycines

The addition of carbon and heteroatom nucleophiles to (bicyclo[5.1.0]octadienyl)Fe(CO)2L+ cations 5 or 8 (L = CO, PPh3) generally proceeds via attack at the dienyl terminus on the face of the ligand opposite to iron to generate 6-substituted (bicyclo[5.1.0]octa-2,4-diene)iron complexes (11 or 13). In certain cases, these products are unstable with respect to elimination of a proton and the nucleophilic substituent to afford (cyclooctatetraene)Fe(CO)2L (4 or 7). Decomplexation of 13f, arising from addition of phthalimide to 8, gave N-(bicyclo[5.1.0]octa-3,5-dien-2-yl)phthalimide (19). Oxidative cleavage of 19 (RuCl3/NaIO4) followed by esterification gave the cyclopropane diester 22, which upon hydrolysis gave cis-2-(2′ -carboxycyclopropyl)glycine (CCG-III, 18) (eight steps from 4, 43% overall yield). This methodology was also utilized for preparation of stereospecifically deuterated CCG-III (d-18) and optically enriched (-)-18. Deprotonation of 22 resulted in cyclopropane ring opening to afford the benzoindolizidine (23).

Facile synthesis of (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine an isotype-selective agonist of metabotropic glutamate receptors

(2S,1'S,2'S)-2-(Carboxycyclopropyl)glycine (L-CCG-I) was synthesized in 12 steps and 14% overall yield by using Sharpless's asymmetric dihydroxylation reaction and stereochemically controlled cyclopropanation as key steps.

Synthesis of Four Diastereomeric L-2-(Carboxycyclopropyl)glycines. Conformationally Constrained L-Glutamate Analogues

To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereochemically L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues o