1-n-heptyltrispiro<2.0.2.0.2.0>nonane

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1-n-heptyltrispiro<2.0.2.0.2.0>nonane
• 英文别名: 8-Heptyltrispiro[2.0.24.0.27.03]nonane；8-heptyltrispiro[2.0.24.0.27.03]nonane
• 化学式: C₁₆H₂₆
• 分子量: 218.382
• InChiKey: ZYVTUQOAMPFGDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  endo-7-chloro-7-methyl-1-n-heptyldispiro<2.0.2.1>heptane 在 palladium diacetate 、 potassium tert-butylate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 1-n-heptyltrispiro<2.0.2.0.2.0>nonane
  参考文献：
  名称：

  Strain Energies in [n]Triangulanes and Spirocyclopropanated Cyclobutanes: An Experimental Study

  摘要：

  The enthalpies of formation for trispiro[2.0.0.2.1.1]nonane (3), [3]rotane (4), n-heptyl[3]rotane (6), spiro-[2.3]hexane (7), and the isomeric dispiro[2.0.2.2]octane (8) and dispiro[2.1.2.1]octane (9), as well as [4]rotane (10), have been determined by measuring their heats of combustion in a microcalorimeter; these values and the strain energies (SE) derived from them are compared with values from MM2/MM3 calculations. The results confirm previously reported theoretical and experimental values for spiropentane and establish an additivity scheme for strain energies in all sorts of [n]triangulanes, with an excessive strain energy increment of 8.6 kcal/mol per spiro carbon atom. Such an additional strain increment is virtually nonexistent for 7 (0.8 +/- 0.4 kcal/mol), 8 (0.6 +/- 0.2 kcal/mol), and 9 (0.3 +/- 0.3 kcal/mol) but is significant for 10, with Delta SE = 2.4 +/- 0.5 kcal/mol. Therefore, a simple additivity of strain energies without an excess increment can be employed for spirocyclopropanated cyclobutanes as well as larger rings including [n]rotanes (n > 4).

  DOI：

  10.1021/ja00153a006

文献信息

• Strain Energies in [n]Triangulanes and Spirocyclopropanated Cyclobutanes: An Experimental Study
  作者：H.-D. Beckhaus、C. Ruechardt、S. I. Kozhushkov、V. N. Belov、S. P. Verevkin、A. de Meijere

  DOI：10.1021/ja00153a006

  日期：1995.12

  The enthalpies of formation for trispiro[2.0.0.2.1.1]nonane (3), [3]rotane (4), n-heptyl[3]rotane (6), spiro-[2.3]hexane (7), and the isomeric dispiro[2.0.2.2]octane (8) and dispiro[2.1.2.1]octane (9), as well as [4]rotane (10), have been determined by measuring their heats of combustion in a microcalorimeter; these values and the strain energies (SE) derived from them are compared with values from MM2/MM3 calculations. The results confirm previously reported theoretical and experimental values for spiropentane and establish an additivity scheme for strain energies in all sorts of [n]triangulanes, with an excessive strain energy increment of 8.6 kcal/mol per spiro carbon atom. Such an additional strain increment is virtually nonexistent for 7 (0.8 +/- 0.4 kcal/mol), 8 (0.6 +/- 0.2 kcal/mol), and 9 (0.3 +/- 0.3 kcal/mol) but is significant for 10, with Delta SE = 2.4 +/- 0.5 kcal/mol. Therefore, a simple additivity of strain energies without an excess increment can be employed for spirocyclopropanated cyclobutanes as well as larger rings including [n]rotanes (n > 4).