3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione (HCID 89529)

概要

reagent used in peptide synthesis; structure

名称と識別子

優先名称: 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione
IUPAC: 4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
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
英語名: N-Hydroxy-5-norbornene-2,3-dicarboximide
分子式: C9H9NO3
分子量: 179.17

名称と別名

21715-90-2N-Hydroxy-5-norbornene-2,3-dicarboximideDTXSID608851784,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-RefChem:8301273a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneDTXCID401024572244-538-62-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dioneHONB4-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione4-Hydroxy-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

名称をさらに表示

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N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシイミド(ペプチド合成用)4-ヒドロキシ-4-アザトリシクロ［5．2．1．0（2，6）］デカ-8-エン-3，5-ジオンENDO-N-ヒドロキシビシクロ[2.2.1]ヘプト-5-エン-2,3-ジカルボキシイミドN-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIC ACID IMIDEHONB N-HYDROXY-5-NORBORNENE-2.3-DICARBOXYLIMIDEN-HYDROXY-5-NORBORNENE-2,3-DICARBOXYLIMIDEN-HYDROXY-5-NORBORNENE-2,3-DICARBOXIMIDE (HONB)N-Hydroxy-5-norborneLABOTEST-BB LT00112336Endo-N-Hydroxy-5-Norbornene-2,N-Hydroxynorborna-5-ene-2,3-dicarbimide

SCHEMBL6052Oprea1_006565N-Hydroxy-5-norbornene-2.3-dicarboxylic imideNSC12953EINECS 244-538-6MFCD00167583NSC-12953N-Hydroxybicyclo[2.2.1]-5-heptene-2,3-dicarboximide

データベース識別子

CAS: 21715-90-2
PubChem CID: 89529
DTXSID: DTXSID60885178
EC Number: 244-538-6
Nikkaji: J208.586K

物性

構造計算による物性

XLogP: -0.2
極性表面積: 57.6 Å²
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

物理化学的性質

融点: 165 · 165-170 °C (lit.)
沸点: 311.69 °C · 311.69°C (rough estimate)
比重(密度): 1.2822 · 1.2822 (rough estimate)
屈折率: 1.56 · 1.5600 (estimate)
貯蔵温度: 2 · Sealed in dry,2-8°C
溶解性: エタノールに可溶
酸解離定数(Pka): 9 · 9.00±0.20(Predicted)
外見: 個体
色: オフホワイト
BRN: 13540 · 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 · 21715-90-2(CAS DataBase Reference)
EPAの化学物質情報: 4 · 4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy- (21715-90-2)

化学的性質

化学的特性white to off-white crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 4.2% (2 of 48) of reports.

Warning

H315 (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.

危険有害性情報

Regulatory Information · 2 件

Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23986

4,7-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 CategoriesSkin Irrit. 2 (95.8%)

安全データ

wgk: 3
tsca: TSCA listed
hs_code: 29280090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
ストレージクラス: 11 - Combustible Solids

化学と産業

用途と製造

General Manufacturing Information4,7-Methano-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-hydroxy-: ACTIVE

応用分野 · 3 件

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.

調製方法 · 1 件

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.]