1,7,7-三甲雙環[2.2.1]庚-2-烯 | 464-17-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 1,7,7-三甲雙環[2.2.1]庚-2-烯
• 中文别名: 2-【草(之上)+伯】烯
• 英文名称: 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene
• 英文别名: bornylene；Bornylen；2-bornene；Bornen；2-Bornen；bornene
• CAS: 464-17-5
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: KUKRLSJNTMLPPK-UHFFFAOYSA-N

物化性质

• 熔点：
  113°C
• 沸点：
  185.55°C (rough estimate)
• 密度：
  0.8455 (estimate)
• LogP：
  4.187 (est)
• 保留指数：
  907;896;907

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1,7,7-三甲雙環[2.2.1]庚-2-烯 在 (二氯碘)-苯 作用下， 以 氯仿 为溶剂， 生成 2 endo, 3 exo-trans-Dichlor-bornan
  参考文献：
  名称：

  Masson,S.; Thuillier,A., Bulletin de la Societe Chimique de France, 1969, # 12, p. 4368 - 4377

  摘要：

  DOI：
• 作为产物：
  描述：

  isobornyl chloride 生成 1,7,7-三甲雙環[2.2.1]庚-2-烯
  参考文献：
  名称：

  Reactions of the 2-Bornyl Radical. I. The Decarbonylation of 2-Formylbornane

  摘要：

  DOI：

  10.1021/ja00875a029

文献信息

• Synthesis, Characterization, and Catalytic Activity of NAPO-5 and NAPO-11
  作者：Shanmugam P. Elangovan、Vengaimuthu Krishnasamy、Velayutham Murugesan

  DOI：10.1246/bcsj.68.3659

  日期：1995.12

  Nickel-substituted aluminophosphate molecular sieves (NAPO-5 and NAPO-11) were synthesized hydrothermally using triethylamine and dipropylamine as templates. Structures were confirmed by X-ray powder pattern, and unit cell parameters calculated by a standard least square refinement technique. The isomorphous substitution of nickel in the aluminophosphate framework is evidenced by the considerable increase in unit cell volume compared to unsubstituted AlPO4-5 and AlPO4-11. In addition, electron spin resonance and diffuse reflectance spectra were carried out to produce supporting evidence for the isomorphous substitution of nickel. Acidity was determined by a TPD-TGA method which shows two types of acid sites. Symmetry and asymmetry vibrations were obtained from infrared spectra. Chemical analysis by ICP and BET surface area are also reported. The physicochemical properties of the catalysts were correlated towards isomerisation of camphene at various (WHSV)−1 values and temperatures. The products formed are tricyclene and 2-bornene and the selective formation of tricyclene was achieved over these catalysts.

  通过使用三乙胺和二丙胺作为模板，采用水热合成法制备了镍取代的铝磷酸盐分子筛（NAPO-5和NAPO-11）。结构通过X射线粉末衍射图谱确认，并利用标准最小二乘精修技术计算了晶胞参数。相较于未取代的AlPO4-5和AlPO4-11，单元晶胞体积的显著增加证明了镍在铝磷酸盐骨架中的同晶取代。此外，电子自旋共振和漫反射光谱也为镍的同晶取代提供了支持性证据。酸度通过TPD-TGA方法测定，显示存在两种类型的酸性位点。从红外光谱中获得了对称和非对称振动。通过ICP化学分析和BET比表面积测定也进行了报道。催化剂的物理化学性质与樟脑在不同（WHSV）-1值和温度下的异构化反应相关联。生成的产物为三环烯和2-硼烯，利用这些催化剂实现了对三环烯的选择性形成。
• Salt effects and the mechanism of electrophilic mercuration of unsaturated compounds
  作者：V. R. Kartashov、N. V. Malisova、A. B. Radbil、T. N. Sokolova、O. V. Vasiljeva

  DOI：10.1007/bf00702403

  日期：1995.3

  The reaction of Hg(OAc)2 with bornylene in THF-H2O and CH3CN-H2O mixed solvents (75 ∶ 25, v/v) was studied. The effects of the addition of NaOAc on the reaction rate and the composition of products were investigated. In the CH3CN-H2O mixture, the addition of NaOAc decreases the amount of the rearranged product, fundamentally changes the ratio between the regioisomeric solvoadducts, and promotes the

  研究了Hg(OAc)2与冰片烯在THF-H2O和CH3CN-H2O混合溶剂(75∶25，v/v)中的反应。研究了NaOAc的加入对反应速率和产物组成的影响。在CH3CN-H2O混合物中，NaOAc的加入减少了重排产物的量，从根本上改变了区域异构溶剂加合物的比例，促进了Hg(OAc)2加成产物的形成。反应通过离子对和游离汞离子进行；离子对的阳离子和游离的汞离子具有不同的结构。
• Regiochemistry of the addition of mercury salts to bornylene
  作者：T. N. Sokolova、V. R. Kartashov、I. V. Timofeev、Yu. K. Grishin、N. S. Zefirov

  DOI：10.1007/bf01169727

  日期：1994.3

  The dependence of the regiochemistry of the mercuration of bornylene on the nature of the mercurating reagent and on the solvent has been found. The structures of the intermediate and transition state in these reactions have been proposed.

  已经发现冰片烯汞化的区域化学依赖于汞化试剂的性质和溶剂。已经提出了这些反应中中间态和过渡态的结构。
• Methoxylation of α-pinene over heteropolyacids immobilized in silica
  作者：D.S. Pito、I. Matos、I.M. Fonseca、A.M. Ramos、J. Vital、J.E. Castanheiro

  DOI：10.1016/j.apcata.2009.11.006

  日期：2010.1.31

  immobilized on silica as catalysts, at 60 °C, being the α-terpinyl methyl ether the main product. Tungstophosphoric acid (PW), molybdophosphoric acid (PMo), tungstosilicic acid (SiW) and molybdosilicic acid (SiMo) were immobilized on silica by sol–gel method. It was observed that the catalytic activity of the silica-supported heteropolyacids decreases in the series: PW2_S > SiW_S > PMo_S > SiMo_S. A

  使用固定在二氧化硅上的杂多酸作为催化剂，研究了α-pine烯的甲氧基化反应，该反应是在60°C下进行的，α-pine烯基甲基醚是主要产物。钨-磷酸（PW），钼磷酸（PMo），钨硅酸（SiW）和钼硅酸（SiMo）通过溶胶-凝胶法固定在二氧化硅上。观察到二氧化硅负载的杂多酸的催化活性按以下顺序降低：PW 2_S> SiW_S> PMo_S> SiMo_S。 制备了一系列以不同的PW负载量固定在硅胶上的PW。观察到催化活性随固定在二氧化硅上的PW的量而增加。然而，在二氧化硅上大量的PW时，观察到催化活性降低。 用所有催化剂都获得了对α-叔戊基甲基醚的良好选择性（接近完全转化时约60％）。 PW2_S的催化稳定性通过对同一催化剂样品进行连续分批运行来评估。在第三批之后，观察到初始活性的稳定。 建立动力学模型，假设根据平行反应网络消耗了α-pine烯。观察到动力学模型非常符合实验浓度数据。
• Catalytic transformation of camphene over aluminophosphate-based molecular sieves
  作者：S. P. Elangovan、Banumathi Arabindoo、V. Krishnasamy、V. Murugesan

  DOI：10.1039/ft9959104471

  日期：——

  The catalytic transformation of camphene over AlPO4-5, AlPO4-11, SAPO-5, SAPO-11, VAPO-5, VAPO-11, CoAPO-5, CoAPO-11, NAPO-5, NAPO-11, ZAPO-5 and ZAPO-11 in the vapour phase has been studied. The products formed are tricyclene, bornylene and monocyclic terpenes. The product distribution is influenced by both acidity and inverse weight hourly space velocity (WHSV)–1. Selective formation of tricyclene is envisaged over weak acid sites and with lower (WHSV)–1, while the monocylics like dipentene, terpinolene, α- and τ-terpinenes, p-menthene and p-cymene are formed over strong acid sites. The effect of temperature on conversion and product distribution, and the effect of acidity and (WHSV)–1 on the distribution of monocyclics have also been investigated.

  研究了莰在气相中通过 AlPO4-5、AlPO4-11、SAPO-5、SAPO-11、VAPO-5、VAPO-11、CoAPO-5、CoAPO-11、NAPO-5、NAPO-11、ZAPO-5 和 ZAPO-11 催化转化的情况。生成的产物有三环烯、双烯烃和单环萜烯。产物的分布受酸度和逆重量小时空间速度（WHSV）-1 的影响。弱酸位点和较低的 (WHSV)-1 会选择性地生成三环烯，而单环萜烯如二戊烯、萜品烯、α- 和 τ-萜烯、对门烯和对-氰烯则在强酸位点上生成。此外，还研究了温度对转化率和产物分布的影响，以及酸度和 (WHSV)-1 对单环分布的影响。

表征谱图