Merck
CN
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文件

安全信息

40288

Sigma-Aldrich

6,6-二甲基-5-亚甲基-1,3-环戊二烯

≥95%

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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
经验公式（希尔记法）:
C8H10
CAS号:
2175-91-9
分子量:
106.17
Beilstein:
1616308
MDL编号:
MFCD00011655
PubChem化学物质编号:
57649965
NACRES:
NA.22

质量水平

100

检测方案

≥95%

形式

liquid

折射率

n20/D 1.548 (lit.)
n20/D 1.548

bp

76-77 °C/50 mmHg (lit.)

密度

0.881 g/mL at 25 °C (lit.)

储存温度

−20°C

SMILES string

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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相关类别

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.

象形图

FlameHealth hazard
GHS02,GHS08

警示用语：

Danger

危险声明

H226 - H304

预防措施声明

P210 - P301 + P310 + P331

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

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Functionalization of 6, 6-Dimethylfulvene: A Fulvene Analogue of the Aldol Condensation.
Nystrom JE, et al.
Tetrahedron Letters, 29(39), 4997-5000 (1988)
R W Eaton et al.
Applied and environmental microbiology, 62(3), 756-760 (1996-03-01)
The biotransformation of 6,6-dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene], a nonaromatic C(inf5) carbocyclic analog of isopropylbenzene, was examined by using Pseudomonas putida RE213, a Tn5-generated dihydrodiol-accumulating mutant of the isopropylbenzene-degrading strain P. putida RE204. 6,6-Dimethylfulvene was converted to a single chiral product identified as
Michael H Howard et al.
The Journal of organic chemistry, 68(1), 120-129 (2003-01-08)
Reaction of 2,2-bis(trifluoromethyl)-1,1-dicyanoethylene (BTF; 1) with 6,6-dimethylfulvene (2) affords the expected Diels-Alder cycloadduct, 7-(1-methylethylidene)-3,3-bis(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2,2-dicarbonitrile (3), in good yield. The cycloadduct 3 is unstable and exists in equilibrium with the starting materials in less polar solvents. In more polar environment, the
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)
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)
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