40288
6,6-二甲基-5-亚甲基-1,3-环戊二烯
≥95%
别名:
5-(1-甲基亚乙基)-1,3-环戊二烯, 5-异亚丙基-1,3-环戊二烯
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关于此项目
经验公式（希尔记法）:
C8H10
化学文摘社编号:
分子量:
106.17
Beilstein:
1616308
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
方案
≥95%
表单
liquid
折射率
n20/D 1.548 (lit.)
n20/D 1.548
沸点
76-77 °C/50 mmHg (lit.)
密度
0.881 g/mL at 25 °C (lit.)
储存温度
−20°C
SMILES字符串
C\C(C)=C1/C=CC=C1
InChI
1S/C8H10/c1-7(2)8-5-3-4-6-8/h3-6H,1-2H3
InChI key
WXACXMWYHXOSIX-UHFFFAOYSA-N
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一般描述
6,6-Dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene] is a nonaromatic carbocyclic analog of isopropylbenzene. 6,6-Dimethylfulvene reacts with 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF; 1) to afford the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile. Metal-free hydrogenation of 6,6-dimethylfulvene via frustrated Lewis pair (FLP) mediated triple domino reaction has been reported.The biotransformation of 6,6-dimethylfulvene by Pseudomonas putida RE213 has been studied.Cycloaddition of 6,6-dimethylfulvene with benzynes has been reported.
6,6-Dimethylfulvene undergoes nucleophilic reaction with lithium dichloromethide in the presence of THF at -75°C, selectively at its exocyclic double bond.
应用
6,6-Dimethylfulvene may be employed in the following studies:
- One-pot synthesis of ansa-metallocenes.
- Synthesis of endo and exo-adducts with maleic anhydride.
- Synthesis of fulvenols or the corresponding trimethylsilyl ethers.
警示用语：
Danger
危险声明
危险分类
Asp. Tox. 1 - Flam. Liq. 3
储存分类代码
3 - Flammable liquids
WGK
WGK 3
闪点(°F)
109.4 °F - closed cup
闪点(°C)
43 °C - closed cup
个人防护装备
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
危险化学品
此项目有
The Diels-Alder Reaction and the Rearrangement of the Maleic Anhydride Adducts of 6, 6-Dimethylfulvene.
Craig D, et al.
Journal of the American Chemical Society, 76(18), 4573-4575 (1954)
Carbenic philicity: 6, 6-dimethylfulvene as an indicator substrate.
Moss RA, et al.
Journal of the American College of Cardiology, 103(9), 2413-2415 (1981)
Cycloaddition of 6, 6-Dimethylfulvene with Benzynes1.
Muneyuki R and Tanida H.
The Journal of Organic Chemistry, 31(6), 1988-1990 (1966)
One-Step Synthesis of Organolanthanide (II) Complexes from the Metal.
Recknagel A and Edelmann FT.
Angewandte Chemie (International Edition in English), 30(6), 693-694 (1991)
Sergej Tamke et al.
Organic & biomolecular chemistry, 12(45), 9139-9144 (2014-10-09)
The frustrated Lewis pair (FLP) mediated hydrosilylation of pentafulvenes is described yielding allyl silanes with high regioselectivity in excellent yields. While phenyl substituted allyl silanes undergo B(C6F5)3-mediated rearrangement to vinyl silanes, dimethyl derivatives experience FLP-catalyzed hydrogenation followed by an unprecedented
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