环戊二烯

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环戊二烯





系统名
Cyclopenta-1,3-diene[1]
别名
 茂、CPD
识别
缩写
 CPD, HCp

CAS号
542-92-7  ✓

PubChem
7612

ChemSpider
7330

SMILES


InChI


InChIKey
ZSWFCLXCOIISFI-UHFFFAOYAI

Beilstein
 471171

Gmelin
 1311

EINECS
208-835-4

ChEBI
30664

RTECS
 GY1000000

MeSH
1,3-cyclopentadiene
性质

化学式
 C5H6

摩尔质量
 66.1 g·mol−1

精确质量
 66.046950192 g mol-1
外观
 无色液体

密度
 786 mg cm-3

熔点
 -90 °C（183 K）

沸点
 39-43 °C（312-316 K）

pKa
16

pKb
-2
结构

分子构型
 平面型[2]
热力学

So298K
 182.7 J K-1 mol-1

热容
 115.3 J K-1 mol-1
危险性

欧盟危险性符号


易燃易燃 F


有害有害 Xn


危害环境危害环境N



警示术语
 R：R11-R20/22-R36/37/38-R51/53

安全术语
 S：S2-S36/37-S61

GHS危险性符号

易燃物

有毒

致癌或诱变物质



GHS提示词
 危险

H-术语
 225-301-311-332-371

闪点
 25 °C

MAK
 不固定[3]
相关物质
相关碳氢化合物
苯、环丁二烯
相关化学品
二聚环戊二烯
若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。

环戊二烯（Cyclopentadiene），或称茂[4]，是五个碳的环状二烯烃，分子式为C5H6。环戊二烯室温下为无色液体，具有强烈的刺激性气味，并且通过自身狄尔斯-阿尔德反应迅速聚合生成二聚环戊二烯。二聚环戊二烯加热分解为环戊二烯。不溶于水，易溶于乙醚、苯等溶剂。


环戊二烯可以作为双烯体，与对苯醌等亲双烯体发生狄尔斯-阿尔德反应。[5]


质子核磁共振谱表明，环戊二烯分子内不停发生着氢[1,5]迁移，使得五个环碳原子是等同的。[6] 同样是出于这个原因，取代环戊二烯在发生DA反应时，通常会得到众多异构体产物的混合物。


环戊二烯基（C5H−
5，又称茂基）的碳有一定的酸性，生成的阴离子有六个π电子，具芳香性。环戊二烯与环戊二烯基负离子可以与金属配位生成金属茂配合物。[7] 一个典型的例子是二茂铁。环戊二烯基（Cyclopentadienyl）简写为Cp。


环戊二烯一般得自炼焦时的副产物粗苯或石油热解时的低沸点部分。



参见



  • 芳香性

  • 二聚环戊二烯


  • 甲基环戊二烯（英语：Methylcyclopentadiene）、五甲基环戊二烯

  • 茂金属



参考资料





  1. ^ 1,3-cyclopentadiene - Compound Summary. PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004 [8 October 2011]. 


  2. ^ Valery I. Faustov, Mikhail P. Egorov, Oleg M. Nefedov and Yuri N. Molin. Ab initio G2 and DFT calculations on electron affinity of cyclopentadiene, silole, germole and their 2,3,4,5-tetraphenyl substituted analogs : structure, stability and EPR parameters of the radical anions. Phys. Chem. Chem. Phys. 2000, 2 (19): 4293–4297. doi:10.1039/b005247g. 


  3. ^ Record of CAS RN 542-92-7 in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health）.


  4. ^ 字源：戊意思是五，表示五元环，加上“艹”（有机化合物的偏旁）构成此字


  5. ^ Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto (1998). "2-Cyclohexene-1,4-dione". Org. Synth.; Coll. Vol. 9: 186. 


  6. ^ Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. (1998). Introduction to Organic Chemistry (4th Edn.) Upper Saddle River, NJ: Prentice Hall.


  7. ^ Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J., Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999.ISBN 0-935702-48-2






















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  • 论

  • 编


环烯烃

单烯烃


  • 环丙烯

  • 环丁烯

  • 环戊烯

  • 环己烯

  • 环庚烯（英语：Cycloheptene）

  • 环辛烯（英语：Cyclooctene）

  • 环壬烯（英语：Cyclononene）
二烯烃


  • 环丁二烯

  • 环戊二烯


  • 环己二烯

    • 1,3-环己二烯

    • 1,4-环己二烯




  • 环庚二烯

    • 1,3-环庚二烯（英语：1,3-Cycloheptadiene）

    • 1,4-环庚二烯（英语：1,4-Cycloheptadiene）




  • 环辛二烯（英语：Cyclooctadiene）
    • 1,5-环辛二烯
多烯烃


  • 苯

  • 环庚三烯

  • 环辛四烯

  • 三蝶烯





















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