2-乙烯基双环[2.2.1]庚烷 | 2146-39-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 2-乙烯基双环[2.2.1]庚烷
• 英文名称: 2-vinylnorbornane
• 英文别名: 2-Vinyl-bicyclo<2.2.1>heptan；2-vinylbicyclo<2.2.1>heptane；2-ethenylbicyclo[2.2.1]heptane
• CAS: 2146-39-6
• 化学式: C₉H₁₄
• 分子量: 122.21
• InChiKey: PFUYSXSIHCSVJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  150.1 °C
• 沸点：
  162.66°C (rough estimate)
• 密度：
  0.8900 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  2-乙烯基双环[2.2.1]庚烷 在 Acidic catalyst 三氟化硼 作用下， 反应 7.0h， 生成 1-vinyltricyclo<2.2.1.0^2,6>heptane
  参考文献：
  名称：

  Bobyleva, A. A.; Belikova, N. A.; Kalinichenko, A. N., Journal of Organic Chemistry USSR (English Translation), 1980, p. 1397 - 1403

  摘要：

  DOI：
• 作为产物：
  描述：

  2-<2-Acetoxy-aethyl>-bicyclo<2.2.1>heptan 生成 2-乙烯基双环[2.2.1]庚烷
  参考文献：
  名称：

  BOBYLEVA A. A.; BELIKOVA N. A.; KALINICHENKO A. N.; BARYSHNIKOV A. T.; DU+, ZH. ORGAN. XIMII, 1980, 16, HO 8, 1645-1653

  摘要：

  DOI：

文献信息

• Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
  作者：Junting Chen、Jiakun Li、Matthew B. Plutschack、Florian Berger、Tobias Ritter

  DOI：10.1002/anie.201914215

  日期：2020.3.27

  we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C-H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse-electron-demand hetero-Diels-Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium- and ruthenium-catalyzed cross-coupling reactions to make alkenyl C-C,

  在本文中，我们报道了由未活化的烯烃进行的区域选择性烯基亲电试剂的合成，它是基于直接和区域选择性的CH thththrenation反应。提出该选择性是由于不寻常的反电子需求异Diels-Alder反应引起的。烯基sulf盐可在钯和钌催化的交叉偶联反应中用作亲电子试剂，以使烯基CC，C-Cl，C-Br和C-SCF3键具有立体保留。
• Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines
  作者：Qiang Cheng、Junting Chen、Songyun Lin、Tobias Ritter

  DOI：10.1021/jacs.0c08248

  日期：2020.10.14

  Allylic C–H amination is currently accomplished with (sulfon)amides or carbamates. Here we show the first allylic amination that can directly afford alkyl allylamines, enabled by the reactivity of thianthrene-based nitrogen sources that can be prepared from primary amines in a single step.

  烯丙基 C-H 胺化目前是用（磺）酰胺或氨基甲酸酯完成的。在这里，我们展示了第一个可以直接提供烷基烯丙胺的烯丙基胺化，这是由基于噻蒽的氮源的反应性实现的，该氮源可以在一个步骤中从伯胺制备。
• [EN] CYCLOALKYLNORBORNENE MONOMERS, POLYMERS DERIVED THEREFROM AND THEIR USE IN PERVAPORATION<br/>[FR] MONOMÈRES DE CYCLOALKYLNORBORNÈNE, POLYMÈRES ISSUS DE CEUX-CI ET LEUR UTILISATION EN PERVAPORATION
  申请人：PROMERUS LLC

  公开号：WO2014025735A1

  公开（公告）日：2014-02-13

  Embodiments in accordance with the present invention provide forming various polycycloalkyl polynorbornene polymers and copolymers which are useful for forming pervaporation membranes, the membranes themselves and methods of making such membranes.

  根据本发明的实施例，提供了形成各种聚环戊烯聚合物和共聚物的方法，这些聚合物和共聚物用于形成渗透蒸发膜，以及膜本身和制造这种膜的方法。
• Pd-Catalyzed Decarbonylative Heck Olefination of Aromatic Carboxylic Acids Activated in situ with Di-<i>tert</i>-butyl Dicarbonate
  作者：Lukas J. Gooßen、Jens Paetzold、Lars Winkel

  DOI：10.1055/s-2002-34227

  日期：——

  The first protocol for a direct Heck olefination of aroma­tic carboxylic acids has been developed. By treatment with commercially available di-tert-butyl dicarbonate, the carboxylic acids are converted in situ into the mixed anhydrides, which in the presence of a palladium catalyst react with olefins to give styrene derivatives. As by-products, only volatile CO and CO2 along with tert-butanol are formed, making the work-up of the reaction products particuarly easy. A mixture of PdCl2, LiCl and γ-picoline was identified to be the most effective catalyst system.

  已经开发出一种直接的芳香族羧酸Heck烯化的首个协议。通过与商业可得的二叔丁基二碳酸酯处理，羧酸在原位转化为混合酸酐，在钯催化剂的存在下与烯烃反应，生成苯乙烯衍生物。作为副产物，仅生成挥发性的CO和CO2以及叔丁醇，使反应产物的后处理特别简单。 PdCl2、LiCl和γ-吡啶的混合物被确定为最有效的催化剂体系。
• Mechanism of catalytic migration of the double bond in 2-vinylnorbornanes
  作者：V. V. Zamalyutin、R. S. Shamsiev、V. R. Flid

  DOI：10.1007/s11172-022-3639-3

  日期：2022.10

  Liquid-phase hydrogenation of 5-vinylbicyclo[2.2.1]hept-2-ene (5-vinyl-2-norbornene, VNE) existing as a mixture of endo- and exo-isomers in the presence of a palladium catalyst (0.25% Pd/γ-Al2O3, or PC-25) is a complex consecutive-parallel process proceeding via the formation of (endo/exo)-2-vinylnorbornanes. Subsequent hydrogenation of the latter is preceded by quantitative isomerization of the vinyl group to the ethylidene one. The mechanism of the phenomenon was studied experimentally and theoretically. It was established that isomerization of 2-vinylnorbornanes to 2-ethylidenenorbornanes requires the presence of palladium (as the active component of the catalyst) and hydrogen in the reaction system. All reaction products were identified and the material balance of the process was studied. According to DFT PBE/SBK quantum chemical calculations, migration of the multiple bond in 2-vinylnorbornanes on the Pd(111) face of the model cluster Pd21(H)2 is of allylic character.

  在钯催化剂（0.25% Pd/γ-Al2O3，或 PC-25）存在下，5-乙烯基双环[2.2.1]庚-2-烯（5-乙烯基-2-降冰片烯，VNE）以内向异构体和外向异构体混合物的形式存在，其液相氢化是一个复杂的连续平行过程，通过形成（内向/外向）-2-乙烯基降冰片烯进行。在后者进行氢化之前，乙烯基会定量异构化为亚乙基。对这一现象的机理进行了实验和理论研究。结果表明，2-乙烯基降冰片烷异构化为 2-亚乙基降冰片烷需要反应体系中存在钯（催化剂的活性成分）和氢。对所有反应产物进行了鉴定，并对该过程的物料平衡进行了研究。根据 DFT PBE/SBK 量子化学计算，2-乙烯基降冰片烷中的多键在模型簇 Pd21(H)2 的 Pd(111) 面上的迁移具有烯丙基性质。