5-endo-methoxybicyclo[2.2.1]hept-2-ene | 17190-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-endo-methoxybicyclo[2.2.1]hept-2-ene
• 英文别名: (+/-)-methyl-norborn-5-ene-2endo-yl ether；(+/-)-Methyl-norborn-5-en-2endo-yl-aether
• CAS: 17190-87-3；17190-92-0；56663-04-8
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: RCDOWRWNYHNLLA-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-endo-methoxybicyclo[2.2.1]hept-2-ene 在 sodium dichromate 、 diborane(6) 作用下， 生成 6endo-Methoxy-2endo-norbornanol
  参考文献：
  名称：

  合成并水解von 6内取代基对甲苯磺酸- [2内-降冰片基]酯。Norbornanreihe，9岁。Mitteilung †

  摘要：

  6种内取代2种内-降冰片基对甲苯磺酸酯的合成与水解

  DOI：

  10.1002/hlca.19820650733
• 作为产物：
  描述：

  5-norbornenyl-2-acetate 在 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.75h， 生成 5-endo-methoxybicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  合成并水解von 6内取代基对甲苯磺酸- [2内-降冰片基]酯。Norbornanreihe，9岁。Mitteilung †

  摘要：

  6种内取代2种内-降冰片基对甲苯磺酸酯的合成与水解

  DOI：

  10.1002/hlca.19820650733

文献信息

• Acces aux (R)S acyl-1 vinyl -tolylsulfoxydes a partir du (R)S dimethylamino-2 -tolylsulfinyl-1 ethane. Leurs reactivites en tant que dienophile.
  作者：Christian Maignan、Ahmed Guessous、Francis Rouessac

  DOI：10.1016/s0040-4039(00)84595-5

  日期：1986.1
• 40. Aspects of stereochemistry. Part XI. Epoxide formation in the cyclohexene and bicycloheptene series
  作者：H. B. Henbest、B. Nicholls

  DOI：10.1039/jr9590000221

  日期：——
• Effect of a Methoxy Substituent on the Vinylcyclobutane Carbon Migration
  作者：Phyllis A. Leber、Celina C. Lasota、Neil A. Strotman、Gloria S. Yen

  DOI：10.1021/jo0621017

  日期：2007.2.1

  Over the temperature range 250-300 degrees C, 8-exo-methoxybicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybicyclo[2.2.2]oct-2-enes, 2a and 2b, respectively, with a clear preference for the si product: si/sr = 3.2. Both 1a and its 8-endo epimer 1b experience appreciable epimerization and fragmentation. A long-lived intermediate with weakly interacting diradical centers, one of which is stabilized by a methoxy substituent, can account for all such observations.
• Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXXIII. Hydration of exo- and endo-5-Methoxy-2-norbornenes and 3-Methoxynortricyclane.
  作者：Martti Lajunen、Jouni Jantunen、Päivi Koiranen、B. C. Hauback、Ola Persson、Ruo-Hua Zhang、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0728

  日期：——

  The disappearance of exo- and endo-5-methoxy-2-norbornenes and 3-methoxynortricyclane in aqueous perchloric acid was followed by capillary GC at different temperatures and acid concentrations. The rate constants, activation parameters, solvent deuterium isotope effects, excess acidity plots and products accord with the rate-determining protonation of the double bond or the cyclopropane ring followed mainly by water attack on a methoxy-substituted 2-norbornyl cation (Ad(E)2 mechanism). The excess acidity plots were corrected according to a partial protonation of the ether oxygen atom. No significant cleavage of the ether linkage was observed.
• Synthese und Hydrolyse von 6<i>endo</i>-substituierten<i>p</i>-Toluolsulfonsäure-[2<i>endo</i>-norbornyl]estern. Norbornanreihe, 9. Mitteilung
  作者：Cyril A. Grob、Bettina Günther、Reinhard Hanreich

  DOI：10.1002/hlca.19820650733

  日期：1982.11.3

  The Synthesis and Hydrolysis of 6endo-Substituted 2endo-Norbornyl p-Toluenesulfonates

  6种内取代2种内-降冰片基对甲苯磺酸酯的合成与水解