Bicyclo<8.1.0>undecane | 286-92-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: Bicyclo<8.1.0>undecane
• 英文别名: cis-Bicyclo<8.1.0>undecan；Bicyclo[8.1.0]undecane
• CAS: 286-92-0
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: ZGGJKSINQDYFJN-UHFFFAOYSA-N

物化性质

• 沸点：
  214.0±7.0 °C(Predicted)
• 密度：
  0.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  Bicyclo<8.1.0>undecane 在 chromium trioxide-3,5-dimethylpyrazole 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到trans-Bicyclo<8.1.0>undecan-2-one
  参考文献：
  名称：

  三氧化铬–3,5-二甲基吡唑配合物：用于氧化环丙基碳氢化合物的温和选择性试剂

  摘要：

  标题配合物选择性地氧化与环丙烷环相邻的亚甲基单元，产生相应的环丙基酮和/或由三元环的裂解产生的产物的合成有用的产率。

  DOI：

  10.1039/c39930000954
• 作为产物：
  描述：

  氯碘甲烷 、 (Z)-cyclodecene 在 diethylzinc 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以87%的产率得到Bicyclo<8.1.0>undecane
  参考文献：
  名称：

  A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents

  摘要：

  A study comparing the rate of cyclopropanation of a range of olefins using (chloromethyl)- and (iodomethyl)zinc reagents is described. The (chloromethyl)zinc reagent derived from diethylzinc and chloroiodomethane is generally more reactive than the (iodomethyl)zinc analogue. The use of 1,2-dichloroethane as the solvent for these reactions was shown to be a crucial factor necessary to achieve clean, rapid, high-yielding cyclopropanations. The well-known directing effect of proximal oxygen substituents on the stereochemical outcome of "Simmons-Smith" cyclopropanations was shown to hold for the (chloromethyl)zinc reagent as well. The diethylzinc/chloroiodomethane reagent system in 1,2-dichloroethane should prove to be a valuable alternative to traditional (iodomethyl)zinc-based cyclopropanation reagents.

  DOI：

  10.1021/jo00025a007

文献信息

• A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents
  作者：Scott E. Denmark、James P. Edwards

  DOI：10.1021/jo00025a007

  日期：1991.12

  A study comparing the rate of cyclopropanation of a range of olefins using (chloromethyl)- and (iodomethyl)zinc reagents is described. The (chloromethyl)zinc reagent derived from diethylzinc and chloroiodomethane is generally more reactive than the (iodomethyl)zinc analogue. The use of 1,2-dichloroethane as the solvent for these reactions was shown to be a crucial factor necessary to achieve clean, rapid, high-yielding cyclopropanations. The well-known directing effect of proximal oxygen substituents on the stereochemical outcome of "Simmons-Smith" cyclopropanations was shown to hold for the (chloromethyl)zinc reagent as well. The diethylzinc/chloroiodomethane reagent system in 1,2-dichloroethane should prove to be a valuable alternative to traditional (iodomethyl)zinc-based cyclopropanation reagents.
• The chromium trioxide–3,5-dimethylpyrazole complex: a mild and selective reagent for the oxidation of cyclopropyl hydrocarbons
  作者：Martin G. Banwell、Najiba Haddad、Julie A. Huglin、Maureen F. MacKay、Monica E. Reum、John H. Ryan、Kathleen A. Turner (née Herbert)

  DOI：10.1039/c39930000954

  日期：——

  The title complex selectively oxidises the methylene unit adjacent to a cyclopropane ring producing synthetically useful yields of the corresponding cyclopropyl ketones and/or products resulting from cleavage of the three-membered ring.

  标题配合物选择性地氧化与环丙烷环相邻的亚甲基单元，产生相应的环丙基酮和/或由三元环的裂解产生的产物的合成有用的产率。