4-オキソ-2-アゼチジンカルボン酸

4-Oxoazetidine-2-carboxylic acid

HCID 3488064CAS 98019-65-9

部分構造検索類似構造を探す

基本情報

標準SMILES: O=C1CC(C(=O)O)N1
InChIKey: YSPMLLKKKHCTBN-UHFFFAOYSA-N
分子式: C4H5NO3
平均分子量: 115.09 g/mol
単同位体質量: 115.02694302

名称と識別子

優先名称: 4-Oxoazetidine-2-carboxylic acid
IUPAC: 4-oxoazetidine-2-carboxylic acid
現地名: 4-オキソ-2-アゼチジンカルボン酸
英語名: 4-Oxoazetidine-2-carboxylic acid
分子式: C4H5NO3
分子量: 115.09

名称と別名

4-oxoazetidine-2-carboxylic AcidRefChem:526202869-806-54-oxo-2-azetidinecarboxylic acid98019-65-94-Oxo-azetidine-2-carboxylic acidMFCD007981602-Azetidinecarboxylic acid, 4-oxo-4-carboxy-2-azetidinone4-Carboxyazetidin-2-one4-carboxyazetidine-2-oneSCHEMBL690090

名称をさらに表示

4-オキソ-2-アゼチジンカルボン酸(2R)-2-azetidinone-4-carboxylic acid

4-oxo-2-azetidinecarboxylicacid4-hydroxycarbonylazetidine-2-oneDTXSID80392950YSPMLLKKKHCTBN-UHFFFAOYSA-NAKOS006227845CS-W019929PB21715PB27000

データベース識別子

CAS: 98019-65-9
PubChem CID: 3488064
DTXSID: DTXSID80392950
EC Number: 869-806-5

物性

構造計算による物性

XLogP: -1.1
極性表面積: 66.4 Å²
水素結合供与体数: 2
水素結合受容体数: 3
回転可能結合数: 1
重原子数: 8
形式電荷: 0
複雑度: 142

物理化学的性質

沸点: 489.4 · 489.4±38.0 °C(Predicted)
比重(密度): 1.519 · 1.519±0.06 g/cm3(Predicted)
貯蔵温度: 2 · under inert gas (nitrogen or Argon) at 2-8°C
酸解離定数(Pka): 3.19 · 3.19±0.20(Predicted)
InChI: InChI=1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)
InChIKey: YSPMLLKKKHCTBN-UHFFFAOYSA-N
SMILES: N1C(=O)CC1C(O)=O

安全と法規制

GHS分類

GHS Classification · 5 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

安全データ

hazard_class: IRRITANT

化学と産業

応用分野 · 1 件

説明4-Oxoazetidine-2-carboxylic acid may be interpreted as a cyclic mimetic of the amino acid Asp. Due to the high reactivity of the four-membered ring, this molecule can serve as an “electrophilic trap” in reactions with nucleophiles. 4-oxoazetidine-2-carboxylic acid can be used as a building block for developing enzyme inhibitors, particularly protease inhibitors. It undergoes coupling reactions with amino acids and oligopeptide esters. Following desilylation of the amino acid residue and deprotection, free β-lactam peptides are obtained[1].