tricyclo[5.2.1.0^{2,6}]deca-3,8-diene

• ChemBase编号: 108886
• 分子式: C10H12
• 平均质量: 132.20228
• 单一同位素质量: 132.09390038
• SMILES: C1C=CC2C3CC(C=C3)C12
• Canonical SMILES: C1=CC2C(C1)C1C=CC2C1
• InChI: InChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2
• InChIKey: HECLRDQVFMWTQS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: tricyclo[5.2.1.0^{2,6}]deca-3,8-diene; tricyclo[5.2.1.0^2,^6]deca-3,8-diene
• IUPAC传统名: dicyclopentadiene
• 别名: 二环戊二烯; DICYCLOPENTADIENE; 1,3-Dicyclopentadiene; Dicyclopentadiene; Cyclopentadiene dimer; 3a,4,7,7a-Tetrahydro-4,7-methanoindene

登记号

• CAS号: 77-73-6
• EC号: 247-724-5; 201-052-9
• MDL号: MFCD00078246
• Beilstein号: 1904092
• 默克索引号: 142739
• PubChem SID: 162088921
• PubChem CID: 6492
• Chemspider ID: 6247
• KEGG ID: C14411
• 医学主题词(MeSH): Dicyclopentadiene
• 维基百科标题: Dicyclopentadiene

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.1641932
• LogD (pH = 7.4): 2.1641932
• Log P: 2.1641932
• 摩尔折射率: 44.4292 cm^3
• 极化性: 16.519753 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Liquid
• 熔点: 32.5 °C; 6°C
• 沸点: 170 °C; 170°C; 171-173°C
• 闪点: 26°C(78°F); 32 °C
• 密度: 0.977 g/ml; 0.98 g/cm^3; 0.982
• 折射率: 1.5100

安全信息

• RTECS编号: PC1050000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); X
• 联合国危险货物编号: UN 2048; UN2048
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): III
• 危险公开号: 11-20/22-36/37/38-51/53; R:11-20/22-36/37/38-51/53
• 安全公开号: 36/37-61; S:61-36/37
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS07; GHS09
• NFPA704:
  

  3

  1

  1
• GHS危险声明: H225-H302-H332-H315-H319-H335-H411
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A

产品相关信息

• 纯度: 90+%, stab. with 4-tert-butylcatechol; typically 95%, stab.

详细说明

MP Biomedicals - 05209108

MP Biomedicals Rare Chemical collection

参考文献

• Source, on heating, of monomeric cyclopentadiene. For details, see: Org. Synth. Coll., 7, 339 (1990).
• The cyclopentadienyl anion reacts with carbonyl compounds with the formation of fulvenes. For example using KOH and 18-crown-6, see: Synthesis, 799 (1980).
• Diels-Alder reaction with 1,4-benzoquinones and subsequent retro Diels-Alder with elimination of cyclopentadiene have been used in synthesis of 2-cyclohexene-1,4-diones: J. Chem. Soc. (C), 124 (1969); Org. Synth. Coll., 9, 186 (1998). For an enantioselective, catalytic Diels-Alder reaction, see: Org. Synth. Coll., 9, 67 (1998).
• Readily deprotonated by strong bases to give the 6πAlpha/Delectron cyclopentadienyl anion, which forms stable complexes with many transition metals. Conversion to ferrocene by two alternative procedures: Org. Synth. Coll., 4, 473 (1963), or using crown-ether catalysis: Angew. Chem. Int. Ed., 18, 792 (1979). Preparation of ruthenocene: Org. Synth. Coll., 5, 1001 (1973).
• For a review of methods for the synthesis of a wide variety of 1,3-bifunctionalized cyclopentanes and cyclopentenes from cyclopentadiene, see: Angew. Chem. Int. Ed., 21, 480 (1982).