(1β,5β)-6,8-ジオキサビシクロ[3.2.1]オクタ-2-エン-4-オン

Levoglucosenone

HCID 699486

ノート反応

部分構造検索類似構造を探す

基本情報

CAS: 37112-31-5
標準SMILES: O=C1C=C[C@H]2CO[C@@H]1O2
InChIKey: HITOXZPZGPXYHY-UJURSFKZSA-N
分子式: C6H6O3
平均分子量: 126.11 g/mol

概要

Levoglucosenone is an anhydrohexose and a deoxyketohexose.

名称と識別子

優先名称: Levoglucosenone
IUPAC: (1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one
現地名: (1β,5β)-6,8-ジオキサビシクロ[3.2.1]オクタ-2-エン-4-オン
英語名: Levoglucosenone
分子式: C6H6O3
分子量: 126.11

名称と別名

Levoglucosenone37112-31-5CHEBI:30999B7N23SN1LB1,6-Anhydro-3,4-dideoxyhex-3-enopyran-2-ulose1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose6,8-DIOXABICYCLO(3.2.1)OCT-2-EN-4-ONE, (1S,5R)-DTXSID70880912RefChem:153211DTXCID001022255(1S,5R)-6,8-dioxabicyclo(3.2.1)oct-2-en-4-one;1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyranos-2-ulose(1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one

名称をさらに表示

2β,6β-(エポキシメタノ)-2H-ピラン-3(6H)-オン(2R,6S)-2,6-エポキシ-6,7-ジヒドロオキセピン-3(2H)-オンレボグルコセノン(1S,5R)-6,8-ジオキサビシクロ[3.2.1]オクタ-2-エン-4-オン(2R)-2β,6β-(エポキシメタノ)-3,6-ジヒドロ-2H-ピラン-3-オン(1β,5β)-6,8-ジオキサビシクロ[3.2.1]オクタ-2-エン-4-オン(1S,5R)-6,8-ジオキサビシクロ[3.2.1]オクト-2-エン-4-オン(1α,5α)-7,8-ジオキサビシクロ[3.2.1]オクタ-3-エン-2-オン2β,6β-(エポキシメタノ)-6H-ピラン-3(2H)-オン(-)-レボグルコセノン(1S,5R)-Levoglucosenone>Levoglucosenone min. 98%Levoglucosenone, 10 mM in DMSO6,8-DIOXA-BICYCLO[3.2.1]OCT-2-EN-4-ONE2β,6β-(Epoxymethano)-2H-pyran-3(6H)-one(1s)-8-dioxabicyclo(3.2.1)oct-2-en-4-one

BRN 4859778CHEMBL4126941(1S)-6,8-Dioxabicyclo(3.2.1)oct-2-en-4-oneMFCD001916641,6-ANHYDRO-3,4-DIDEOXY-.BETA.-D-GLYCERO-HEX-3-ENOPYRANOS-2-ULOSECCRIS 4274UNII-B7N23SN1LBBCP07825

データベース識別子

CAS: 37112-31-5
PubChem CID: 699486
ChEMBL: CHEMBL4126941
ChEBI: CHEBI:30999
UNII: B7N23SN1LB
EC Number: 640-811-2
Nikkaji: J405.523C

物性

構造計算による物性

XLogP: -0.2
極性表面積: 35.5 Å²
水素結合供与体数: 0
水素結合受容体数: 3
回転可能結合数: 0
重原子数: 9
形式電荷: 0
複雑度: 173

物理化学的性質

比旋光度: 25 · D25 -460° (c = 1.0 in CHCl3) (Halpern, 1973); D31 -514.8° (c = 0.3 in CHCl3) (Taniguchi).
沸点: 113 °C/3mmHg · 113°C/3mmHg(lit.)
比重(密度): 1.329 · 1.329±0.06 g/cm3(Predicted)
屈折率: 25 · nD25 1.5084
貯蔵温度: -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
溶解性: クロロホルム（適量）、DMSO（微量）、酢酸エチル（微量）
外見: 液体
色: 無色～黄色
Merck: 14 · 14,5465
安定性: 光に敏感
InChI: InChI=1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4-,6+/m0/s1
InChIKey: HITOXZPZGPXYHY-UJURSFKZSA-N
SMILES: [C@@]12([H])O[C@@]([H])(OC1)C(=O)C=C2
LogP: -0.74 · -0.740 (est)

化学的性質

化学的特性Colourless to Yellow Oil

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information6,8-Dioxabicyclo3.2.1oct-2-en-4-one, (1S,5R)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk: WGK 3
rtecs: JG7020000
hs_code: 2932990090
risk_code: 36
消防法: 危-4-3-III
safety_code: 26
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2
ストレージクラス: 10 - Combustible liquids

化学と産業

応用分野 · 1 件

使用(-)-Form Levoglucosenone is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, its very useful as a chiral source for synthesizing natural products.