二螺[2.1.2.1]辛烷 | 25399-32-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 二螺[2.1.2.1]辛烷
• 英文名称: Dispiro <2.1.2.1>octan
• 英文别名: dispiro<2.1.2.1>octane；Dispiro<2.1.2.1>octan；dispiro[2.1.2.1]octane；Dispiro-<2.1.2.1>-octan；Dispiro[2.1.2.1]octan；dispiro[2.1.25.13]octane
• CAS: 25399-32-0
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: CGEYHDBRZXGTLN-UHFFFAOYSA-N

物化性质

• 沸点：
  152.8±7.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  二螺[2.1.2.1]辛烷 在 sodium periodate 、 四氧化钌 作用下， 反应 24.0h， 以86%的产率得到Dispiro<2.1.2.1>octanon-4
  参考文献：
  名称：

  在与原位生成的RuO 4的氧化反应中，环丙烷作为活化基团的作用

  摘要：

  将在Sharpless条件下原位生成的四氧化钌应用于不同的含环丙烷基团的烃，这些环丙烷基团是螺链烷烃化的或环稠合的。在所有情况下，氧化仅在环丙基的α位发生，得到酮。当这些位置是三级时，观察到环裂解。

  DOI：

  10.1016/0040-4039(96)00325-5
• 作为产物：
  描述：

  1,1-双(溴甲基)环丙烷 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 乙醇 、 edetate disodium 、 potassium carbonate 、 sodium iodide 、 锌 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 29.0h， 生成 二螺[2.1.2.1]辛烷
  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

• Binger, Paul; Doyle, Michael J.; Benn, Reinhard, Chemische Berichte, 1983, vol. 116, # 1, p. 1 - 10
  作者：Binger, Paul、Doyle, Michael J.、Benn, Reinhard

  DOI：——

  日期：——
• Etude des petits cycles—XXXVII
  作者：J.M. Denis、P. Le Perchec、J.M. Conia

  DOI：10.1016/0040-4020(77)80094-x

  日期：1977.1
• Catalytic conversions of cyclic C3-olefins in the presence of metal complexes. 6. Effect of P(NEt2)3 ligand on the properties of complex Ni(O) catalyst in oligomerization of methylenecyclopropane
  作者：D. B. Furman、M. K. Munshieva、A. O. Ivanov、A. Yu. Belyankin、L. N. Morozova、L. S. Isaeva、D. B. Tagiev、D. P. Kravtsov、O. V. Bragin

  DOI：10.1007/bf00957976

  日期：1991.3

  Preferential formation of di- or trimers of methylenecyclopropane (MCP) under the influence of Ni(O) complexes is determined by the nature of ligands, additions of modifiers, and the reaction conditions. The Ni(O) complex with coordinated P(NEt2)3 was synthesized via a proposed intermediate catalytic system Ni(COD)2-P(NEt2)3 by the interaction between Ni(eta-3-C3H5)2 and P(NEt2)3. The composition of the complex: Ni[P(NEt2)3]2}x (K-1) was established by H-1 and P-31H-1} NMR, EPR spectroscopy, IR diffuse reflectance spectroscopy, and GLC. In the range 20-60-degrees-C complex K-1 only brings about trimerization of MCP. The catalytic properties of K-1 were described earlier by a proposed scheme for the catalytic conversion of MCP under the influence of Ni(O) complexes.
• Catalytic conversions of C3 cyclic olefins in the presence of Ni(O) complexes Communication 1. (?2-methylenecyclopropane)bis(triphenylphosphine)nickel: Catalytic activity and role in dimerization and trimerization of methylenecyclopropane
  作者：D. B. Furman、A. V. Kudryashev、L. S. Isaeva、T. A. Peganova、A. O. Ivanov、S. V. Zotova、V. S. Bogdanov、O. V. Bragin、D. N. Kravtsov

  DOI：10.1007/bf00956646

  日期：1987.6
• 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).

表征谱图