5-ethylidenebicyclo[2.2.1]hept-2-ene | 28304-66-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 5-ethylidenebicyclo[2.2.1]hept-2-ene
• 英文别名: 5-ethylidene-2-norbornene；2-ethylidene-5-norbornene；5-ethylidenenorbornene；ethylidene-norbornene；ethylidenenorbornene；5-Ethylidene-2-norbornene, (Z)-；(5Z)-5-ethylidenebicyclo[2.2.1]hept-2-ene
• CAS: 28304-66-7
• 化学式: C₉H₁₂
• mdl: MFCD24390166
• 分子量: 120.194
• InChiKey: OJOWICOBYCXEKR-WAPJZHGLSA-N

物化性质

• 沸点：
  159.22°C (rough estimate)
• 密度：
  0.8900 (rough estimate)
• 物理描述：
  Ethylidene norbornene is a colorless liquid with an odor of turpentine. Flash point 101°F. Floats on water.
• 颜色/状态：
  COLORLESS LIQUID
• 气味：
  TURPENTINE-LIKE
• 熔点：
  FP: -80 °C
• 闪点：
  38.33 °C, open cup
• 溶解度：
  less than 1 mg/mL at 64° F (NTP, 1992)
• 蒸汽密度：
  Relative vapor density (air = 1): 4.1
• 蒸汽压力：
  4.2 MM HG @ 20 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 燃烧热：
  (EST) -10,450 CAL/G
• 气味阈值：
  An odor threshold of 0.014 ppm has been reported.
• 保留指数：
  911;905;910;915;916;921

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 暴露途径

该物质可以通过吸入和摄入被身体吸收。

The substance can be absorbed into the body by inhalation and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛、皮肤、鼻子、喉咙刺激；头痛；咳嗽，呼吸困难；恶心，呕吐；嗅觉、味觉改变；化学性肺炎（吸入液体）；在动物中：肝脏、肾脏、泌尿生殖器损伤；骨髓效应

irritation eyes, skin, nose, throat; headache; cough, dyspnea (breathing difficulty); nausea, vomiting; olfactory, taste changes; chemical pneumonitis (aspiration liquid); In Animals: liver, kidney, urogenital injury; bone marrow effects

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 吸入症状

混淆。 咳嗽。 头痛。 呼吸困难。 喉咙痛。

Confusion. Cough. Headache. Shortness of breath. Sore throat.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

红斑。疼痛。

Redness. Pain.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

反应信息

• 作为反应物：
  描述：

  5-ethylidenebicyclo[2.2.1]hept-2-ene 生成 1-乙烯基双环[2.2.1]庚-2-烯
  参考文献：
  名称：

  Processes for Correlating UV-VIS Spectra of Norbornene Compound to Polymerization Processes Using the Same, and Related Purification Methods and Compositions

  摘要：

  该发明提供了一种聚合乙烯和至少一种α-烯烃的方法，该方法包括在5-乙烯基-2-去氢-2-环辛烯的存在下聚合乙烯和至少一种α-烯烃，所述5-乙烯基-2-去氢-2-环辛烯的杂质水平较低，由以下波长处的吸光度确定：320 nm和343 nm。该发明还提供了一种提高催化剂效率的方法，以及一种在聚合乙烯和至少一种α-烯烃的存在下，通过测定上述波长处的吸光度来确定预期催化剂效率的方法。该发明还提供了一种纯化5-乙烯基-2-去氢-2-环辛烯以形成纯化的5-乙烯基-2-去氢-2-环辛烯的方法，所述5-乙烯基-2-去氢-2-环辛烯的杂质水平较低，由上述波长处的吸光度确定。

  公开号：

  US20090312511A1
• 作为产物：
  描述：

  5-乙烯基双环[2.2.1]庚-2-烯 在 aluminum oxide 、 sodium 作用下， 以 正庚烷 为溶剂， 生成 5-ethylidenebicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Duschek,C. et al., Journal fur praktische Chemie (Leipzig 1954), 1977, vol. 319, p. 77 - 82

  摘要：

  DOI：

文献信息

• Rhodium-Catalyzed Coupling Reaction of Aroyl Chlorides with Alkenes
  作者：Toru Sugihara、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1002/adsc.200404145

  日期：2004.12

  Aroyl chlorides react with acyclic and cyclic alkenes in the presence of a rhodium catalyst to give Mizoroki–Heck type and cyclization products, respectively. A rhodium-ethylene complex, [RhCl(C2H4)2}2], showed excellent performance for these reactions. Notably, the reactions can be conducted effectively under base- and phosphane-free conditions.

  在铑催化剂的存在下，芳酰氯与无环和环状烯烃反应，分别得到Mizoroki-Heck型和环化产物。铑-乙烯络合物[RhCl（C 2 H 4）2 } 2 ]显示出对于这些反应的优异性能。值得注意的是，该反应可以在无碱和无膦的条件下有效地进行。
• Preparation of New Solid Superbase and Its Catalytic Activity
  作者：Gohfu Suzukamo、Masami Fukao、Masao Minobe

  DOI：10.1246/cl.1987.585

  日期：1987.4.5

  successive treatment of γ-alumina with sodium hydroxide and sodium at 280–350 °C under nitrogen. The base was highly effective in the catalytic isomerization of 5-vinylbicyclo[2.2.1]hept-2-ene to 5-ethylidenebicyclo[2.2.1]hept-2-ene.

  通过在氮气下在 280-350°C 下用氢氧化钠和钠连续处理 γ-氧化铝制备碱度（H-）高于 37 的固体超强碱。该碱在将 5-乙烯基双环[2.2.1]庚-2-烯催化异构化为5-亚乙基双环[2.2.1]庚-2-烯中非常有效。
• Superbase character of alumina loaded with potassium by impregnation from ammoniacal solution
  作者：Toshihide Baba、Haruhisa Handa、Yoshio Ono

  DOI：10.1039/ft9949000187

  日期：——

  Al2O3 has been loaded with potassium by impregnation from an ammoniacal solution and heated under vacuum at 573 K. The resulting catalyst [K(NH3)/Al2O3] showed extremely high catalytic activity for the isomerization of alkenes. These catalysts had much greater activity than that of Al2O3 loaded with alkali metals by vapour deposition. The isomerization, over K(NH3)/Al2O3, of pent-1-ene to pent-2-ene gave a 98% yield in 6 min at 201 K. The temperature-programmed desorption and IR spectra of Al2O3 after impregnation indicated that the metal amide-like species formed on the alumina is a catalytically active species.Al2O3 loaded with KNH2 was found to be more active than K(NH3)/Al2O3 for the isomerization of 2,3-dimethylbut-1-ene. The basic strength of these catalysts was estimated to be at least H–= 37.

  Al2O3通过从氨盐溶液中浸渍负载了钾，并在573 K下真空加热。所得催化剂[K(NH3)/Al2O3]对烯烃的异构化表现出极高的催化活性。这些催化剂的活性远高于通过气相沉积负载碱金属的Al2O3。在K(NH3)/Al2O3上，1-戊烯异构化为2-戊烯的产率在201 K下为98%，反应时间为6分钟。氨浸渍后Al2O3的温度程序脱附和红外光谱表明，在铝土矿上形成的金属氨基物种是具有催化活性的物种。负载有KNH2的Al2O3在2,3-二甲基戊-1-烯的异构化中被发现比K(NH3)/Al2O3更具活性。这些催化剂的碱性强度估计至少为H–= 37。
• Jones, G. Alun; Stirling, Charles J. M.; Bromby, Norman G., Journal of the Chemical Society. Perkin transactions II, 1983, p. 385 - 394
  作者：Jones, G. Alun、Stirling, Charles J. M.、Bromby, Norman G.

  DOI：——

  日期：——
• KASYAN, L. I.;GALAFEEVA, M. F.;KOVALENKO, V. V.;DRYUK, V. G., YKP. XIM. ZH., 53,(1987) N 9, 960-963
  作者：KASYAN, L. I.、GALAFEEVA, M. F.、KOVALENKO, V. V.、DRYUK, V. G.

  DOI：——

  日期：——