3,4-dihydro-2H-pyran

• ChemBase编号: 69501
• 分子式: C5H8O
• 平均质量: 84.11642
• 单一同位素质量: 84.05751488
• SMILES: C1CCC=CO1
• Canonical SMILES: C1COC=CC1
• InChI: InChI=1S/C5H8O/c1-2-4-6-5-3-1/h2,4H,1,3,5H2
• InChIKey: BUDQDWGNQVEFAC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,4-dihydro-2H-pyran
• IUPAC传统名: dihydropyran
• 别名: 3,4-二氢-2H-吡喃; 2,3-Dihydro-4H-pyran; 3,4-Dihydro-2H-pyran; 3,4-Dihydro-2H-pyran; 2,3-Dihydropyran; DIHYDROPYRAN

登记号

• CAS号: 110-87-2
• EC号: 203-810-4
• MDL号: MFCD00006558
• Beilstein号: 103493
• PubChem SID: 24863242; 162035227; 24893341
• PubChem CID: 8080
• Chemspider ID: 7789
• 维基百科标题: Dihydropyran

理论计算性质

• 里宾斯基五规则: true
• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 0.9868946
• LogD (pH = 7.4): 0.9868946
• Log P: 0.9868946
• 摩尔折射率: 25.2476 cm^3
• 极化性: 9.660139 Å^3
• 极化表面积: 9.23 Å^2
• 可自由旋转的化学键: 0

分子性质

理化性质

• 外观: Colorless liquid
• 熔点: -70 °C(lit.); -70°C; -70°C
• 沸点: 85-86°C; 85-86°C; 86 °C(lit.); 86°C
• 闪点: -15.5°C; -15°C(5°F); -16 °C; -16°C; 3.2 °F
• 密度: 0.922; 0.922 g/ml; 0.922 g/mL; 0.922 g/mL at 25 °C(lit.); 0.926; 1 g/ml
• 折射率: 1.441; 1.4420; n20/D 1.440(lit.); n20/D 1.441
• 蒸汽密度: 2.9 (vs air)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Highly Flammable/Irritant/Air Sensitive/Light Sensitive/Store under Argon; IRRITANT
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 2376; UN2376
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 2YE
• 危险公开号: 11-36/37/38; R:11-36/37/38
• 安全公开号: 16-26-36; 7/9-16-23-26-37; S:16-20-25-26-37/39
• 欧盟危险货物分类: F1
• 欧盟危险识别号(EUHIN): 3B
• 美国ERG指导号: 127
• TSCA收录: false; 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225-H315-H319-H335
• GHS警示性声明: P210-P261-P280G-P305+P351+P338-P403+P233; P210-P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2376 3/PG 2

产品相关信息

• 纯度: ~97-98%; ≥95.0% (GC); 95+%; 97%; 98%; 99%
• 级别: purum
• 杂质: ≤3% tetrahydropyran
• Empirical Formula (Hill Notation): C5H8O

详细说明

MP Biomedicals - 05204025

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150907

Purity: Approx. 97-98%
Widely used hydroxyl-protecting (-OH) reagent.

Sigma Aldrich - D106208

Application
广泛使用的羟基保护试剂。1
包装
100, 500 mL in glass bottle

Sigma Aldrich - 37350

Other Notes
醇的基团保护试剂1,2

参考文献

• Synth. Commun. , 9 : 271 (1979).
• Protects OH groups as their tetrahydropyranyl, (THP) ethers, stable to bases, Grignard or organolithium reagents, metal hydrides, etc., but readily removed by mild acid. Introduction (acetal formation) generally employs an acid catalyst, often p-TsOH. For example of protection, reaction with Grignard, and deprotection, see: Org. Synth. Coll., 7, 334 (1990). For alternative catalysts for THP ether formations, see: Pyridinium p-toluenesulfonate, A15708, Triphenylphosphine hydrobromide, L14290, Boron trifluoride diethyl etherate, A15275, Amberlyst? 15, 89079, Montmorillonite K10, L15160, Acetonyltriphenylphosphonium bromide, B22434, Indium(III) trifluoromethanesulfonate, 40131. Sulfuric acid/silica gel: Synth. Commun., 22, 159 (1992), allows the catalyst to be removed by simple filtration. POCl₃, described for the protection of diethyl hydroxymethylphosphonate, permits use in the Horner-Wadsworth-Emmons reaction: Org. Synth. Coll., 7, 160 (1990). See also Iodotrimethylsilane, A12902, providing non-acidic conditions; cf also Tetrahydropyran, A13392. For selective monotetrahydropyranylation of symmetrical diols, catalyzed by acidic ion-exchange resin, Dowex? 50WX2 50-100 (H), L13943, see: J. Org. Chem., 63, 8183 (1998).
• For selective deprotection of THP ethers under non-acidic conditions with LiCl in wet DMSO, see: J. Org. Chem., 61, 6038 (1996).
• The lithio-derivative, formed with tert-BuLi, reacts with, e.g. alkyl iodides or carbonyl compounds: Tetrahedron Lett., 4187 (1977).
• Acetals and ortho esters, in the presence of Lewis acid catalysts, add readily to the vinyl ether system: Chem. Lett., 1101 (1988).