214027
1,2,3,4,5-五甲基环戊二烯
95%
别名:
1,2,3,4,5-五甲基-1,3-环戊二烯
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关于此项目
经验公式（希尔记法）:
C10H16
化学文摘社编号:
分子量:
136.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-743-4
Beilstein/REAXYS Number:
1849832
MDL number:
Assay:
95%
InChI key
WQIQNKQYEUMPBM-UHFFFAOYSA-N
InChI
1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3
SMILES string
CC1C(C)=C(C)C(C)=C1C
assay
95%
refractive index
n20/D 1.474 (lit.)
bp
58 °C/13 mmHg (lit.)
density
0.87 g/mL at 25 °C (lit.)
Quality Level
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General description
研究了顺磁性内层金属富勒烯与 1，2，3，4，5-五甲基环戊二烯的 Diels-Alder 反应机理。报道了 1，2，3，4，5-五甲基环戊二烯的三步法大规模合成。用激光烧蚀质谱法研究了 1，2，3，4，5-五甲基环戊二烯 (HCp*) 在气相中与钯离子的反应。它与富含电子的烯烃发生自由基阳离子催化的环加成反应，生成 Diels-Alder 产物。
Application
1,2,3,4,5-五甲基环戊二烯用作：
- 五羰基铁中的金属有机溶剂蒸汽沉积中的生长调节剂化学品。
- 通过肟的中间体将醇催化转化为酰胺的“一锅法”铱中的配体。
- 合成[Cp*Rh(bpy)H2O]2+（Cp* = 五甲基环戊二烯基，bpy = 2,2′-联吡啶），它是 NADH 再生过程中的电子介质。
An improved synthesis of 1,2,3,4,5-pentamethylcyclopentadiene.
Kohl FX and Jutzi P.
Journal of Organometallic Chemistry, 243(1), 119-121 (1983)
Synth. React. Inorg. Met.-Org. Chem. , 24, 395-395 (1994)
Reactions of actinide ions with pentamethylcyclopentadiene: atypical hydrocarbon activation.
Gibson JK.
International Journal of Mass Spectrometry, 202(1), 19-29 (2000)
Satoru Sato et al.
Journal of the American Chemical Society, 135(15), 5582-5587 (2013-03-23)
The reaction mechanism of the Diels-Alder reaction of paramagneticendohedral metallofullerene, La@C82, and 1,2,3,4,5-pentamethylcyclopentadiene was studied theoretically and experimentally. Theoretical calculations revealed that this reaction proceeds via a concerted mechanism that includes formation of a stable intermediate. The activation energy of
The Aminium Salt and Photoinduced Electron Transfer Initiated Diels-Alder Cycloaddition of Electron-rich Allenes: Evidence for a Stepwise Mechanism and the Importance of Steric and Electronic Effects for the Reactivity of Distonic Radical Cation Intermediates.
Schmittel M, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 2(8), 1031-1040 (1996)
商品
The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.
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