3-(2-Hydroxy-2-bicyclo[2.2.1]hept-5-enyl)bicyclo[2.2.1]hept-5-en-2-one | 104323-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Hydroxy-2-bicyclo[2.2.1]hept-5-enyl)bicyclo[2.2.1]hept-5-en-2-one
• CAS: 104323-62-8；133161-66-7；133161-76-9；133161-77-0；133161-78-1；133161-79-2；133267-34-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: KRJLSROHJJOJAS-UHFFFAOYSA-N

物化性质

• 熔点：
  111-115 °C
• 沸点：
  367.6±42.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  双环[2.2.1]庚-5-烯-2-酮 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醚 为溶剂， 反应 0.25h， 以60%的产率得到3-(2-Hydroxy-2-bicyclo[2.2.1]hept-5-enyl)bicyclo[2.2.1]hept-5-en-2-one
  参考文献：
  名称：

  Stereoselectivity of organometallic reagents addition to 7-oxabicyclo[2.2.1]hept-5-en-2-one

  摘要：

  DOI：

  10.1021/jo00278a032

文献信息

• Alkylation and oligomerization of the lithium enolate of 2-norbornenones. Stereochemical consequences of enolate aggregation
  作者：John H. Horner、Marisol Vera、John B. Grutzner

  DOI：10.1021/jo00372a021

  日期：1986.10
• Isodicyclopentadienes and related molecules. 53. Unsymmetrical oxidative cleavage of cyclic ketones. Conversion to .omega.-ethoxycarbonyl aldoximes under alkaline conditions
  作者：Cornelis M. Moorhoff、Leo A. Paquette

  DOI：10.1021/jo00002a040

  日期：1991.1

  A useful procedure for effecting the direct unsymmetrical cleavage of an enolizable cyclic ketone to an oximino ester has been developed. The process begins by deprotonation with LDA and is followed by the addition of ethyl nitrite in THF at low temperature. Rapid reaction customarily ensues with resultant overall nitrosolysis. Of particular importance is the facile application of this procedure to substrate ketones that are otherwise sensitive to acidic environments. This feature is exemplified in particular in the case of syn- and anti-sesquinorbornenones 34 and 35, access to which is described for the first time. Since the entire process is executed in a single flask, the methodology is very convenient to implement in practice.
• Hutchinson, J. H.; Li, D. L. F.; Money, T., Canadian Journal of Chemistry, 1991, vol. 69, # 3, p. 558 - 566
  作者：Hutchinson, J. H.、Li, D. L. F.、Money, T.、Palme, M.、Agharahimi, M. R.、Albizati, K. F.

  DOI：——

  日期：——
• MOORHOFF, CORNELIS M.;PAQUETTE, LEO A., J. ORG. CHEM., 56,(1991) N, C. 703-710
  作者：MOORHOFF, CORNELIS M.、PAQUETTE, LEO A.

  DOI：——

  日期：——