5-triethoxysilyl-norbornene

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-triethoxysilyl-norbornene
• 英文别名: 5-(triethoxysilyl)bicyclo[2.2.1]hept-2-ene；[(1S,4S)-2-bicyclo[2.2.1]hept-5-enyl]-triethoxysilane
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: HHKDWDAAEFGBAC-LAGVYOHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙烯 、 5-triethoxysilyl-norbornene 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 24.0h， 以99%的产率得到1,3-divinyl-4-triethoxysilylcyclopentane
  参考文献：
  名称：

  Ethenolysis of silicon containing cycloolefins

  摘要：

  In this paper the ring-opening cross-metathesis of silicon substituted norbornenes with ethene is reported. Silicon containing norbornenes could be selectively ring-opened via a cross-metathesis with ethene employing Ru-based catalysts (RuCl2-(PCy3)(=CHSiMe3) (3) or RuCl2(PCy3)(2)(=CHPh) (4)). It was also found that for the ethenolysis, the order of sequence of the individual reagents is of crucial importance. Under mild reaction conditions and by premixing of ethene and the catalyst before the silicon containing norbornene (C13H24O3Si (5) or C12H24OSi2 (6)) was added, it was possible to convert 5 and 6 into the desired silicon containing alpha,omega-diooelefins quantitatively. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00124-8
• 作为产物：
  描述：

  乙烯基三乙氧基硅烷 、 二聚环戊二烯 反应 2.0h， 以46.8%的产率得到5-triethoxysilyl-norbornene
  参考文献：
  名称：

  二茂铁-钯（II）杂蝎酸酯络合物对降冰片烯衍生物的可切换聚合

  摘要：

  全文通过钯 (II) 二茂铁​​异蝎酸酯络合物对降冰片烯衍生物进行可切换聚合 Mark Abubekerov、Scott M. Shepard 和 Paula L. Diaconescu* 摘要：二茂铁螯合异蝎酸酯络合物 [fc(PPh 2 )(BH[(3, 5-Me) 2 pz] 2 )]PdMe ((fc P,B )PdMe, fc = 1,1'-二茂铁，pz = 吡唑) 催化降冰片烯和降冰片烯衍生物在用 [ Ac Fc] 氧化后的加成聚合反应BAr F ] (乙酰基二茂铁四(3,5-双(三氟甲基)苯基)硼酸盐)。[(fc P,B )PdMe][BAr F ] 在取代降冰片烯存在下的原位还原导致催化活性显着降低。添加一当量的氧化剂可恢复活性。引言乙烯基聚降冰片烯由于其优异的热稳定性而成为光学应用的重要材料，高玻璃化转变温度、小双折射和介电损耗。1- 然而，聚降冰片烯很脆，即使在高分子量

  DOI：

  10.1002/ejic.201501295

文献信息

• Synthesis of Novel Palladium Complexes Containing β‐Diketonate and NHC Ligands and their Catalytic Ability for Addition Polymerizations of the Functional Norbornenes
  作者：Dong Jin Lee、Myungwoong Kim、Chan Kyung Kim、Ik Mo Lee

  DOI：10.1002/bkcs.11761

  日期：2019.7

  containing various N‐heterocyclic carbene (NHC) ligands have been successfully synthesized by the reaction with various β‐diketonate complexes. Treatments of Pd(acac)2 with NHC salts such as 1,3‐di(2,6‐diisopropylphenyl)imidazolium chloride (IPr·HCl) or 1,3‐di(mesityl)imidazolium chloride (IMes·HCl) resulted in [Pd(acac)(NHC)Cl] complexes and these complexes were characterized by NMR. Moreover, these

  通过与各种β-二酮酸酯配合物反应，已成功合成了包含各种N-杂环卡宾（NHC）配体的钯配合物。用NHC盐（例如1,3-二（2,6-二异丙基苯基）咪唑氯化物（IPr·HCl）或1,3-二（间甲苯基）咪唑氯化物（IMes·HCl）处理Pd（acac）2导致[ Pd（acac）（NHC）Cl]配合物，这些配合物用NMR表征。而且，这些钯配合物对各种官能降冰片烯的加成聚合反应显示出中等至良好的催化活性。已经充分研究了各种反应参数对功能性降冰片烯聚合反应的催化活性的影响。
• Novel Pd Catalysts with β-Diketiminates for Homopolymerization of Functionalized Norbornene Derivatives in Water/Organic Mixed Solvents
  作者：Eung Jun Lee、Wook Kyoung Won、Byoungki Lee、Youn Hee Kye、Ik Mo Lee

  DOI：10.5012/bkcs.2013.34.9.2720

  日期：2013.9.20

  Polynorbornenes prepared by vinyl addition pathway are known to have some desirable characteristics for wider application but they have some critical drawbacks such as brittleness, poor solubility and adhesion. In order to improve these drawbacks, extensive research for the successful homo- and copolymerization of polar functionalized norbornene with olefin has been carried out. Even though considerable advance has been achieved in the polymerization of polar functionalized monomers, successful catalytic systems for the homopolymerization of polar functionalized norbornene are rare. In this study, a novel successful catalytic system for the polymerization of polar functionalized norborene is proposed. This system employs Pd $\beta}$-diketiminate/borate cocatalyst in water/organic mixed solvents and it is unique due to introduction of water as a component of solvents. Polymers obtained in this study show high Mw with narrow PDI. Effects of several reaction parameters to the polymer activity and properties are investigated and optimal catalytic system are proposed.

  通过 vinyl 加成途径制备的聚诺尔博烯已知具有一些适合更广泛应用的优良特性，但也存在一些关键缺点，如脆性差、溶解性差和粘附性差。为了改善这些缺点，已针对极性官能化诺尔博烯与烯烃的成功均聚和共聚反应进行了广泛研究。尽管在极性官能化单体的聚合方面已取得相当大的进展，成功的催化体系用于极性官能化诺尔博烯的均聚反应仍然很少。在本研究中，提出了一种新颖且成功的催化体系，用于极性官能化诺尔博烯的聚合。该体系在水/有机混合溶剂中采用 Pd $\beta}$-二酮胺/硼酸盐助催化剂，其独特之处在于将水作为溶剂的成分引入。本研究中获得的聚合物显示出高分子量和窄的分子量分布指数（PDI）。研究了多个反应参数对聚合活性和性质的影响，并提出了优化的催化体系。
• Ethenolysis of silicon containing cycloolefins
  作者：Kamelia Karlou-Eyrisch、Bettina K.M Müller、Christian Herzig、Oskar Nuyken

  DOI：10.1016/s0022-328x(00)00124-8

  日期：2000.7

  In this paper the ring-opening cross-metathesis of silicon substituted norbornenes with ethene is reported. Silicon containing norbornenes could be selectively ring-opened via a cross-metathesis with ethene employing Ru-based catalysts (RuCl2-(PCy3)(=CHSiMe3) (3) or RuCl2(PCy3)(2)(=CHPh) (4)). It was also found that for the ethenolysis, the order of sequence of the individual reagents is of crucial importance. Under mild reaction conditions and by premixing of ethene and the catalyst before the silicon containing norbornene (C13H24O3Si (5) or C12H24OSi2 (6)) was added, it was possible to convert 5 and 6 into the desired silicon containing alpha,omega-diooelefins quantitatively. (C) 2000 Elsevier Science S.A. All rights reserved.
• Switchable Polymerization of Norbornene Derivatives by a Ferrocene‐Palladium(II) Heteroscorpionate Complex
  作者：Mark Abubekerov、Scott M. Shepard、Paula L. Diaconescu

  DOI：10.1002/ejic.201501295

  日期：2016.6

  Polymerization of Norbornene Derivatives by a Palladium(II) Ferrocene Heteroscorpionate Complex Mark Abubekerov, Scott M. Shepard, and Paula L. Diaconescu* Abstract: The ferrocene-chelating heteroscorpionate complex [fc(PPh 2 )(BH[(3,5-Me) 2 pz] 2 )]PdMe ((fc P,B )PdMe, fc = 1,1’- ferrocenediyl, pz = pyrazole) catalyzes the addition polymerization of norbornene and norbornene derivatives upon oxidation with

  全文通过钯 (II) 二茂铁​​异蝎酸酯络合物对降冰片烯衍生物进行可切换聚合 Mark Abubekerov、Scott M. Shepard 和 Paula L. Diaconescu* 摘要：二茂铁螯合异蝎酸酯络合物 [fc(PPh 2 )(BH[(3, 5-Me) 2 pz] 2 )]PdMe ((fc P,B )PdMe, fc = 1,1'-二茂铁，pz = 吡唑) 催化降冰片烯和降冰片烯衍生物在用 [ Ac Fc] 氧化后的加成聚合反应BAr F ] (乙酰基二茂铁四(3,5-双(三氟甲基)苯基)硼酸盐)。[(fc P,B )PdMe][BAr F ] 在取代降冰片烯存在下的原位还原导致催化活性显着降低。添加一当量的氧化剂可恢复活性。引言乙烯基聚降冰片烯由于其优异的热稳定性而成为光学应用的重要材料，高玻璃化转变温度、小双折射和介电损耗。1- 然而，聚降冰片烯很脆，即使在高分子量