1-Methoxybicyclo<3.3.1>nonane | 63160-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Methoxybicyclo<3.3.1>nonane
• 英文别名: Methoxy bicyclo[3.3.1]nonane；1-methoxybicyclo[3.3.1]nonane
• CAS: 63160-90-7
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: XNYMGJWICHVNMA-UHFFFAOYSA-N

物化性质

• 沸点：
  189.6±8.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲醇 、 bicyclo[3.3.1]nonan-1-carboxylic acid 反应 2.0h， 以57.8%的产率得到1-Methoxybicyclo<3.3.1>nonane
  参考文献：
  名称：

  Baklan, V. F.; Khil'chevskii, A. N.; Kukhar', V. P., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 2101 - 2103

  摘要：

  DOI：

文献信息

• Foiled Conjugation in α-Oximino Carbocations
  作者：Xavier Creary、Ziqi Jiang

  DOI：10.1021/jo960073u

  日期：1996.1.1

  The 4-CHNOCH3 group is a cation-stabilizing group when placed in the para-position of a cumyl cation. The effect of this group on cumyl cations when flanked by adjacent methyl groups has now been determined. Solvolysis rates of 3,5-(CH3)(2)-4-(CHNOCH3)cumyl trifluoroacetates are somewhat slower than that of 3,5-dimethylcumyl trifluoroacetate. This is attributed to steric inhibition of the cation-stabilizing resonance effect of the p-oximino group. In a l-adamantyl system, where an alpha-oximino group has been placed directly adjacent to a developing cationic center, solvolysis rates relative to l-adamantyl mesylate are slowed by a factor of 10(8). This is attributed a cation-destabilizing inductive effect where geometric constraints prevent stabilizing orbital overlap of the cationic center with the adjacent alpha-oximino group. This cation-destabilizing effect fades in the homoadamantyl and the bicyclo[3.3.1]nonyl systems, where rate-retarding effects are 1.6 x 10(4) and 1.5 x 10(2), respectively. The behavior of geometrically constrained alpha-oximino cations parallels that of analogously constrained allylic cations. Computational studies at the HF/6-31G* level indicate that twisting the alpha-oximino group out of planarity with a tertiary cationic center into a perpendicular arrangement decreases stabilization by 21 kcal/mol. These studies suggest that conjugative interactions, and not ground state destabilization, are the most important factors in controlling rates of formation of alpha-oximino cations from mesylates and trifluoroacetates.
• (E)-Bicyclo[3.3.1]non-1-ene
  作者：John R. Wiseman、James E. Kipp

  DOI：10.1021/ja00381a036

  日期：1982.8
• WISEMAN, J. R.;KIPP, J. E., J. AMER. CHEM. SOC., 1982, 104, N 17, 4688-4689
  作者：WISEMAN, J. R.、KIPP, J. E.

  DOI：——

  日期：——
• BAKLAN, V. F.;XILCHEVSKIJ, A. N.;KUXAR, V. P., ZH. ORGAN. XIMII, 23,(1987) N 11, 2381-2384
  作者：BAKLAN, V. F.、XILCHEVSKIJ, A. N.、KUXAR, V. P.

  DOI：——

  日期：——
• Baklan, V. F.; Khil'chevskii, A. N.; Kukhar', V. P., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 2101 - 2103
  作者：Baklan, V. F.、Khil'chevskii, A. N.、Kukhar', V. P.

  DOI：——

  日期：——