3,3'-dibromo<1,1'-bibicyclo<1.1.1>pentane> | 125642-45-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 3,3'-dibromo<1,1'-bibicyclo<1.1.1>pentane>
• 英文别名: 3,3'-dibromo-1,1'-bis(bicyclo<1.1.1>pentane)；3,3'-Dibrom-1,1'-bi(bicyclo<1.1.1>pentan)；3,3'-dibromo<2>staffane；3,3'-dibromo(1,1'-bibicyclo[1.1.1]pentane)；1-bromo-3-(3-bromo-1-bicyclo[1.1.1]pentanyl)bicyclo[1.1.1]pentane
• CAS: 125642-45-7
• 化学式: C₁₀H₁₂Br₂
• 分子量: 292.013
• InChiKey: KRXMIFKFMLLNIC-UHFFFAOYSA-N

物化性质

• 熔点：
  >175 °C
• 沸点：
  284.9±35.0 °C(Predicted)
• 密度：
  2.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  3,3'-dibromo<1,1'-bibicyclo<1.1.1>pentane> 在 三正丁基氢锡 作用下， 以 乙醚 为溶剂， 反应 9.0h， 生成 1,1'-Bi(bicyclo<1.1.1>pentan)
  参考文献：
  名称：

  [n]烷烃的红外光谱

  摘要：

  The IR spectra of the rust five oligomers of [1.1.1]propellane ([n]staffanes, n = 1-5), and some of their bridgehead-deuteriated derivatives, have been measured in argon matrix isolation. IR transition moment directions were obtained using stretched polyethylene as solvent. Assignments were based on a simple model of interacting subunits and on comparison with 3-21G HF calculations. IR peaks particularly suitable for use in the determination of orientation of the staffane moieties in supramolecular assemblies have been identified.

  DOI：

  10.1021/j100204a016
• 作为产物：
  描述：

  [1.1.1]螺桨烷 在 溴丙二酸二甲酯 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 2.0h， 以68%的产率得到1-bromo-3-(bismethoxycarbonylmethyl)bicyclo<1.1.1>pentane
  参考文献：
  名称：

  Zefirov, N. S.; Surmina, L. S.; Sadovaya, N. K., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 11, p. 2002 - 2014

  摘要：

  DOI：

文献信息

• Toward a molecular-size tinkertoy construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane
  作者：Piotr Kaszynski、Andrienne C. Friedli、Josef Michl

  DOI：10.1021/ja00028a029

  日期：1992.1

  of [n]staffanes (the oligomers of [1.1.1]propellane n=1-5) functionalized on one or both ends is described,and their properties are summarized. The substituents are -COOCH 3 ,-n-C 4 H 9 ,-C 6 H 5 ,-Br,-I and -SCOCH 3 , and their conversion to others,such as -COOH, -COCH 3 and -SH,is demonstrated. it is proposed that these rod-shaped molecules will be useful in the development of a molecular-size civil

  描述了一种在一端或两端官能化的 [n]staffanes（[1.1.1]propellane 的低聚物 n=1-5）的简便但低场合成，并总结了它们的性质。取代基为-COOCH 3 、-nC 4 H 9 、-C 6 H 5 、-Br、-I 和-SCOCH 3 ，并证明了它们向其他取代基如-COOH、-COCH 3 和-SH 的转化。建议这些棒状分子将有助于开发类似于儿童玩具建筑套装的分子大小的土木工程建筑套装
• Reactions of [1.1.1]propellane
  作者：Kenneth B. Wiberg、Sherman T. Waddell

  DOI：10.1021/ja00162a022

  日期：1990.3

  The free radical addition reactions of [1.1.1] propellane (1) are described in some detail and allowed the preparation of a wide variety of 1,3-disubstituted bicyclo [1.1.1.] pentanes. The reaction of 1 with free radicals was more rapid than that of bicyclo [1.1.0] butane (2), whereas bicyclo [2.1.0] pentane (3) was relatively inert

  [1.1.1] 推进烷 (1) 的自由基加成反应进行了一些详细的描述，并允许制备各种 1,3-二取代双环 [1.1.1.] 戊烷。1 与自由基的反应比双环 [1.1.0] 丁烷 (2) 更快，而双环 [2.1.0] 戊烷 (3) 相对惰性
• Synthesis of doubly bridgehead substituted bicyclo[1.1.1]pentanes. Radical transformations of bridgehead halides and carboxylic acids
  作者：Piotr Kaszynski、Neil D. McMurdie、Josef Michl

  DOI：10.1021/jo00001a058

  日期：1991.1

  Synthetic transformations of the 1-bicyclo[1.1.1]pentyl bridgehead radicals 11 generated from the corresponding bridgehead iodides 3 and carboxylic acids 5 are described. The relatively high nucleophilicity of these radicals was utilized in reactions with carbonyl compounds. In the reaction sequence of preparation of the iodides 3 and their further transformations, [1.1.1]propellane (2) is a synthetic equivalent of the recently described bicyclo[1.1.1]penta-1,3-dienyl dianion (8).
• Gleiter, Rolf; Pfeifer, Karl-Heinz; Szeimies, Guenter, Angewandte Chemie, 1990, vol. 102, # 4, p. 418 - 420
  作者：Gleiter, Rolf、Pfeifer, Karl-Heinz、Szeimies, Guenter、Bunz, Uwe

  DOI：——

  日期：——
• [n]Staffanes: a molecular-size "Tinkertoy" construction set for nanotechnology. Preparation of end-functionalized telomers and a polymer of [1.1.1]propellane
  作者：Piotr. Kaszynski、Josef. Michl

  DOI：10.1021/ja00223a070

  日期：1988.7