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214027

Sigma-Aldrich

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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About This Item

经验公式（希尔记法）:
C10H16
CAS号:
4045-44-7
分子量:
136.23
Beilstein:
1849832
EC號碼:
223-743-4
MDL號碼:
MFCD00001354
分類程式碼代碼:
12352100
PubChem物質ID:
24852821
NACRES:
NA.22

品質等級

200

化驗

95%

折射率

n20/D 1.474 (lit.)

bp

58 °C/13 mmHg (lit.)

密度

0.87 g/mL at 25 °C (lit.)

SMILES 字串

CC1C(C)=C(C)C(C)=C1C

InChI

1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3

InChI 密鑰

WQIQNKQYEUMPBM-UHFFFAOYSA-N

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一般說明

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。

應用

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。

象形圖

Flame
GHS02

訊號詞

Warning

危險聲明

H226

危險分類

Flam. Liq. 3

儲存類別代碼

3 - Flammable liquids

水污染物質分類（WGK）

WGK 3

閃點（°F）

111.2 °F - closed cup

閃點（°C）

44 °C - closed cup

個人防護裝備

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

从最新的版本中选择一种：

分析证书(COA)

Lot/Batch Number
BCBV7825
BCBS9206V
BCBJ9905V
1451030V
1451029V

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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
Reactions of actinide ions with pentamethylcyclopentadiene: atypical hydrocarbon activation.
Gibson JK.
International Journal of Mass Spectrometry, 202(1), 19-29 (2000)
Nathan A Owston et al.
Organic letters, 9(1), 73-75 (2006-12-29)
[reaction: see text] The iridium catalyst [Ir(Cp*)Cl2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in
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)
Journal of Organometallic Chemistry, 472, 359-359 (1994)
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Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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