bicyclo[2.2.1]hept-5-en-2-ylmethyl lbenzoate | 135560-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bicyclo[2.2.1]hept-5-en-2-ylmethyl lbenzoate
• 英文别名: (+/-)-2endo-benzoyloxymethyl-norbornene-(5)；(+/-)-2endo-Benzoyloxymethyl-norbornen-(5)；[(1R,2R,4R)-2-bicyclo[2.2.1]hept-5-enyl]methyl benzoate
• CAS: 135560-45-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: IVXACWABDOBWNU-XBFCOCLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bicyclo[2.2.1]hept-5-en-2-ylmethyl lbenzoate 在 Ni(dmp)2 氧气 、 异丁醛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以83.8%的产率得到Benzoic acid (1R,2S,4R,5R,6S)-1-(3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl)methyl ester
  参考文献：
  名称：

  镍 (II) 配合物催化的分子氧和醛环氧化烯烃的高效方法

  摘要：

  在催化量的双（1,3-二酮基）镍（II）配合物存在下，三取代和外末端烯烃或降冰片烯类似物在用醛处理时顺利单氧化成相应的环氧化物室温下氧气的大气压。

  DOI：

  10.1246/cl.1991.1
• 作为产物：
  描述：

  苯甲酸烯丙酯 、 环戊二烯 反应 8.0h， 以33%的产率得到bicyclo[2.2.1]hept-5-en-2-ylmethyl lbenzoate
  参考文献：
  名称：

  Synthesis of para-substituted bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoates

  摘要：

  para-Substituted bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoates were synthesized by the Diels-Alder reaction of cyclopentadiene with the corresponding para-substituted allyl benzoates, and optimal reaction conditions were found. The product structure was confirmed by independent synthesis and IR and H-1 NMR spectroscopy.

  DOI：

  10.1134/s1070428009010102

文献信息

• Epoxidation of Olefms with Molecular Oxygen and Alcohol Catalyzed by Bis(2-alkyl-1,3-diketonato)oxovanadium(IV)
  作者：Toshihiro Takai、Tohru Yamada、Teruaki Mukaiyama

  DOI：10.1246/cl.1990.1657

  日期：1990.9

  By combined use of molecular oxygen (oxidant) and secondary or primary alcohol (reductant) in the presence of a catalytic amount of bis(2-alkyl-1,3-diketonato)oxovanadium(IV) complexes, norbornene analogues are monooxygenated into the corresponding epoxides in good yields.

  通过在双(2-烷基-1,3-二酮酸根)氧钒(IV)配合物的催化剂量存在下，结合使用分子氧（氧化剂）和次级或初级醇（还原剂），成功地将降冰片烯类似物单氧化为相应的环氧化物，产率良好。
• Controlled molecular design of ether- and ester-bridged norbornenes and their ring-opening metathesis polymerizations
  作者：Alaa S Abd-El-Aziz、Andrea L Edel、Leslie J May、Karen M Epp、Harold M Hutton

  DOI：10.1139/v99-164

  日期：1999.11.1

  A series of functionalized polynorbornenes containing pendent ether- or ester-bridged poly(aromatic ether) chains were prepared. The ether-bridged norbornene complex was synthesized via cyclopentadienyliron-mediated nucleophilic aromatic substitution reactions. This methodology, combined with that of dicyclohexylcarbodiimide-mediated coupling, allowed for the formation of novel oligomeric aryl ether and ester substituted norbornene complexes. Photolytic demetallation gave the monomers in good yields. Structural identification of the exo and endo isomers of both the metallated and demetallated norbornene derivatives was accomplished using HH and CH COSY NMR techniques. Ring-opening metathesis polymerization (ROMP) of these monomers using RuCl₃(hydrate) and (Cy₃P)₂Cl₂Ru=CHPh allowed for the preparation of the functionalized polynorbornenes. Thermal analysis of the resulting polymeric materials demonstrated greater thermal stability as the number of aryl ether groups increased.Key words: aromatic ethers, cyclopentadienyliron, polynorbornene, ROMP, ruthenium catalysts.

  一系列含有侧链醚或酯桥联聚芳醚链的功能化聚诺博烯被制备出来。醚桥联诺博烯配合物是通过环戊二烯基铁介导的亲核芳香取代反应合成的。这种方法与二环己基碳二亚胺介导的偶联相结合，允许形成新型的寡聚芳基醚和酯取代诺博烯配合物。光解金属化反应以良好的产率给出单体。使用HH和CH COSY NMR技术对金属化和去金属化诺博烯衍生物的exo和endo异构体进行了结构鉴定。使用RuCl₃(hydrate)和(Cy₃P)₂Cl₂Ru=CHPh进行开环烯烃转化聚合（ROMP）制备功能化聚诺博烯。所得聚合物的热分析表明，随着芳醚基团数的增加，热稳定性更高。关键词：芳香醚，环戊二烯基铁，聚诺博烯，ROMP，钌催化剂。
• Kukalenko; Melnikow, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 154,156
  作者：Kukalenko、Melnikow

  DOI：——

  日期：——
• Fine-tuned remote control of electrophilic additions to substituted norbornenes
  作者：Odon Arjona、Roberto Fernandez de la Pradilla、Joaquin Plumet、Alma Viso

  DOI：10.1021/jo00021a049

  日期：1991.10
• Synthesis of para-substituted bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoates
  作者：E. G. Mamedbeili (Mamedov)、T. G. Kyazimova、Z. M. Nagiev、O. B. Abdiev、K. A. Aliev

  DOI：10.1134/s1070428009010102

  日期：2009.1

  para-Substituted bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoates were synthesized by the Diels-Alder reaction of cyclopentadiene with the corresponding para-substituted allyl benzoates, and optimal reaction conditions were found. The product structure was confirmed by independent synthesis and IR and H-1 NMR spectroscopy.