3,3'-di-tert-butyl-1,1'-bi(bicyclo[1.1.1]pentane)

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 3,3'-di-tert-butyl-1,1'-bi(bicyclo[1.1.1]pentane)
• 英文别名: 1-Tert-butyl-3-(3-tert-butyl-1-bicyclo[1.1.1]pentanyl)bicyclo[1.1.1]pentane
• 化学式: C₁₈H₃₀
• 分子量: 246.436
• InChiKey: KCXXSCSJAKSBJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  6.0
• 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：

  在 双(乙腈)氯化钯(II) 、 溴甲烷 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以54%的产率得到3,3'-di-tert-butyl-1,1'-bi(bicyclo[1.1.1]pentane)
  参考文献：
  名称：

  A Facile, Palladium-Catalyzed Synthesis of 1,1′-Bi(bicyclo[1.1.1]pentanes)

  摘要：

  Symmetrically 3,3'-disubstituted 1,1'-bi(bicyclo[1.1.1]pentanes) were synthesized in a four-step procedure, using commercially available starting materials, in fair overall yields (51-60%). In this synthesis the final step is an unexpected bridgehead-to-bridgehead homocoupling of bicyclo[1.1.1]pent-1-ylmagnesium halide catalyzed by palladium(II). Only 1.1 mol percent of bis(acetonitrile)palladium(II) chloride and two equivalents of bromomethane were necessary to accomplish this reaction. The bromomethane is essential to convert Pd-0 into Pd-II. The X-ray structure of the [2]staffane 1c has been determined and shows a nonbonded C1-C3 distance of 1.907 Angstrom in the bicyclo[1.1.1]pentyl subunit.

  DOI：

  10.1002/1099-0690(200103)2001:6<1049::aid-ejoc1049>3.0.co;2-v

文献信息

• A Facile, Palladium-Catalyzed Synthesis of 1,1′-Bi(bicyclo[1.1.1]pentanes)
  作者：J. D. Daniel Rehm、Burkhard Ziemer、Günter Szeimies

  DOI：10.1002/1099-0690(200103)2001:6<1049::aid-ejoc1049>3.0.co;2-v

  日期：2001.3

  Symmetrically 3,3'-disubstituted 1,1'-bi(bicyclo[1.1.1]pentanes) were synthesized in a four-step procedure, using commercially available starting materials, in fair overall yields (51-60%). In this synthesis the final step is an unexpected bridgehead-to-bridgehead homocoupling of bicyclo[1.1.1]pent-1-ylmagnesium halide catalyzed by palladium(II). Only 1.1 mol percent of bis(acetonitrile)palladium(II) chloride and two equivalents of bromomethane were necessary to accomplish this reaction. The bromomethane is essential to convert Pd-0 into Pd-II. The X-ray structure of the [2]staffane 1c has been determined and shows a nonbonded C1-C3 distance of 1.907 Angstrom in the bicyclo[1.1.1]pentyl subunit.