1-bromobicyclo<1.1.1>pentane | 128884-80-0

• 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: 1-bromobicyclo<1.1.1>pentane
• 英文别名: 1-bromobicyclo[1.1.1]pentane
• CAS: 128884-80-0
• 化学式: C₅H₇Br
• 分子量: 147.015
• InChiKey: XFXJTOJDGTYWDX-UHFFFAOYSA-N

物化性质

• 沸点：
  96 °C
• 密度：
  1.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  6
• 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：

  1-bromobicyclo<1.1.1>pentane 在 水 作用下， 以 乙醇 为溶剂， 生成 3-羟基-1-亚甲基环丁烷
  参考文献：
  名称：

  溶剂分解3-取代的双环[1.1.1]戊基溴化物中的感应电荷分散

  摘要：

  3-取代的双环[1.1.1]戊基溴化物的溶剂分解速率和产物表明，在离子化为双环[1.1.1]戊基-1-阳离子（3-亚甲基环丁醇的前体）的过程中，极强的感应电荷分散。

  DOI：

  10.1016/s0040-4039(00)79433-0
• 作为产物：
  描述：

  [二环[1.1.1]戊烷-1-羧酸] 在 4-二甲氨基吡啶 、 1-溴-1-氯-2,2,2-三氟乙烷 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-bromobicyclo<1.1.1>pentane
  参考文献：
  名称：

  Della, Ernest W.; Taylor, Dennis K., Australian Journal of Chemistry, 1990, vol. 43, # 5, p. 945 - 948

  摘要：

  DOI：

文献信息

• Unusual bridgehead reactivity: Formation of [1.1.1]Propellane by 1,3-dehydrobromination of 1-bromobicyclo[1.1.1]Pentane.
  作者：Ernest W. Della、Dennis K. Taylor、John Tsanaktsidis

  DOI：10.1016/s0040-4039(00)97847-x

  日期：1990.1

  The reaction between -butyllithium and 1-bromobicyclo[1.1.1]pentane is characterised by 1,3-dehydrobromination and gives [1.1.1]propellane . In the presence of -butyllithium, undergoes ring-opening and yields 3--butylbicyclo[l.l.1]pentyllithium .

  -丁基锂与1-溴二环[1.1.1]戊烷之间的反应的特征在于1，3-脱氢溴化，得到[1.1.1]丙炔。在-丁基锂的存在下，进行开环并产生3--丁基双环[III]戊基锂。
• Adcock, William; Binmore, Gavin T.; Krstic, Alexander R., Journal of the American Chemical Society, 1995, vol. 117, # 10, p. 2758 - 2766
  作者：Adcock, William、Binmore, Gavin T.、Krstic, Alexander R.、Walton, John C.、Wilkie, John

  DOI：——

  日期：——
• Bridgehead Carbocations: A Solvolytic Study of 1-Bromobicyclo[1.1.1]pentane and Its Bridgehead-Substituted Derivatives
  作者：Ernest W. Della、Cyril A. Grob、Dennis K. Taylor

  DOI：10.1021/ja00093a014

  日期：1994.7

  The rate constants (k) for solvolysis of a range of 3-X-substituted bicyclo[1.1.1]pentyl bromides in 80% aqueous ethanol have been measured and a linear relationship found to exist between log k and the inductive/field constant sigma(I). These observations, together with the results of isotope and solvent effect studies described below, have been interpreted as evidence for the formation of 1-bicyclo[1.1.1]pentyl cations in the ionization step in preference to mechanisms in which either ring-opening is concerted with ionization to give 3-methylenecyclobutyl cations or ionization is accompanied by ring-contraction to give bicyclo[1.1.0]butyl-1-carbinyl cations. The latter mechanisms would have been expected to show the effects of strong pi-donor substituent participation, a phenomenon which was not observed. A comparison of the rates of solvolysis of the parent bromide and its 3-deuterated analog is characterized by a large deuterium-isotope effect (k(H)/k(D) = 1.30) which, combined with the observation that 1-bromobicyclo[1.1.1]pentane solvolyses with enhanced rates in solvents which are strong hydrogen bonding accepters, lends support to the view that the 1-bicyclo[1.1.1]pentyl cation derives substantial stabilization from sigma-hyperconjugative interactions.
• DELLA, ERNEST W.;TAYLOR, DENNIS K., AUSTRAL. J. CHEM., 43,(1990) N, C. 945-948
  作者：DELLA, ERNEST W.、TAYLOR, DENNIS K.

  DOI：——

  日期：——
• DELLA, ERNEST W.;TAYLOR, DENNIS K.;TSANAKTSLDLS, JOHN, TETRAHEDRON LETT. , 31,(1990) N6, C. 5219-5220
  作者：DELLA, ERNEST W.、TAYLOR, DENNIS K.、TSANAKTSLDLS, JOHN

  DOI：——

  日期：——