N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシイミド
N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシイミド · N-ヒドロキシビシクロ[2.2.1]ヘプタ-5-エン-2,3-ジカルボキシイミド · N-ヒドロキシノルボルナ-5-エン-2,3-ジカルボイミド · N-ヒドロキシビシクロ[2.2.1]ヘプタ-5-エン-2,3-ジカルボイミド · 4-ヒドロキシ-4-アザトリシクロ[5.2.1.02,6]デカ-8-エン-3,5-ジオン · 2-ヒドロキシ-3a,4,7,7a-テトラヒドロ-4,7-メタノ-1H-イソインドール-1,3(2H)-ジオン · N-ヒドロキシノルボルナ-5-エン-2,3-ジカルボキシミド · 3a,4,7,7a-テトラヒドロ-2-ヒドロキシ-4,7-メタノ-1H-イソインドール-1,3(2H)-ジオン
識別子と物理属性
| CAS No. | 21715-90-2 |
|---|---|
| 分子式 | C9H9NO3 |
| 平均分子量 | 179.17 g/mol |
| 単同位体質量 | 179.05824315 g/mol |
| SMILES | O=C1C2C3C=CC(C3)C2C(=O)N1O |
| InChIKey | ZUSSTQCWRDLYJA-UHFFFAOYSA-N |
| PubChem CID | 89529 |
| EC No. | 244-538-6 |
| DTXSID | DTXSID60885178 |
| 現地名 | N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシイミド |
化学・物理的性質
| XLogP | -0.2 |
|---|---|
| 極性表面積 | 57.6 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 306 |
| 融点 | 165-170 °C (lit.) |
| 沸点 | 311.69°C (rough estimate) |
| 密度 | 1.2822 (rough estimate) |
| 屈折率 | 1.5600 (estimate) |
| 貯蔵条件 | Sealed in dry,2-8°C |
| 溶解度 | エタノールに可溶 |
| pKa（酸解離定数） | 9.00±0.20(Predicted) |
| 外観・状態 | 個体 |
| 色 | オフホワイト |
| BRN | 13540 |
| InChI | InChI=1S/C9H9NO3/c11-8-6-4-1-2-5(3-4)7(6)9(12)10(8)13/h1-2,4-7,13H,3H2 |
| InChIKey | ZUSSTQCWRDLYJA-UHFFFAOYSA-N |
| SMILES | C1(=O)C2C(C3CC2C=C3)C(=O)N1O |
| CAS データベース | 21715-90-2(CAS DataBase Reference) |
| EPAの化学物質情報 | 4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy- (21715-90-2) |
化学的特性
white to off-white crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 4.2% (2 of 48) of reports.WarningH315 (95.8%): Causes skin irritation [Warning Skin corrosion/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)Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/239864,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (95.8%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29280090 |
| 危険文句（R） | 36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
ペプチド合成における添加剤。
説明
N-Hydroxy-5-norbornene-2,3-dicarboximide (NHD) is a compound that has antiviral activity and is used to treat HIV infections. It inhibits the reverse transcriptase enzyme in the virus, which blocks the synthesis of viral DNA. The ferroelectric properties of NHD were first observed by observing changes in its melting point when mixed with water. This property makes it useful for diagnosis purposes. In animal studies, a dose of 5 mg/kg was found to be effective against cancer cells and the drug showed no toxicity in humans at doses up to 500 mg/day. The optimal reaction conditions for NHD are pH 6 and temperature 45 degrees Celsius.
使用
N-Hydroxy-5-norbornene-2,3-dicarboximide(HONB) is used in solution-phase peptide synthesis. Used in the synthesis of enkephalin analogs.
製法・合成法
純化方法
Dissolve the imide in CHCl3, filter, evaporate and recrystallise from EtOAc. IR (nujol): max 1695, 1710 and 1770 (C=O), and 3100 (OH) cm-1. The O-acetyl derivative has m 113-114o (from EtOH) with IR bands at max 1730, 1770 and 1815 cm-1 only, and the O-benzoyl derivative has m 143-144o (from propan-2-ol or *C6H6). [Bauer & Miarka J Org Chem 24 1293 1959, Fujino et al. Chem Pharm Bull Jpn 22 1857 1974]. [Beilstein 21/10 V 188.]