1,3-Bis(1-chlorvinyl)bicyclo<1.1.1>pentan | 127867-23-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,3-Bis(1-chlorvinyl)bicyclo<1.1.1>pentan
• 英文别名: 1,3-di(1-chlorovinyl)bicyclo[1.1.1]pentane；1,3-bis(1-chlorovinyl)bicyclo[1.1.1]pentane；1,3-Bis(1-chloroethenyl)bicyclo[1.1.1]pentane
• CAS: 127867-23-6
• 化学式: C₉H₁₀Cl₂
• 分子量: 189.084
• InChiKey: XZFQZZNRJAXGEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  1,3-Bis(1-chlorvinyl)bicyclo<1.1.1>pentan 在 sodium amide 作用下， 以85%的产率得到1,3-Diethinylbicyclo<1.1.1>pentan
  参考文献：
  名称：

  用于点击化学的双环 [1.1.1] 戊烷衍生结构单元

  摘要：

  描述了双环 [1.1.1] 戊烷衍生的叠氮化物和末端炔烃（点击反应的有趣底物）的合成。除了少数例外，标题化合物是从常见的合成中间体 - 相应的羧酸开始，分两步或三步制备的。1-叠氮双环[1.1.1]戊烷合成的关键步骤是铜催化的重氮转移反应与咪唑-1-磺酰叠氮化物。双环[1.1.1] 戊基取代炔烃的制备依赖于 Seyferth-Gilbert 与 1-重氮-2-氧代丙基-膦酸二甲酯（Ohira-Bestmann 试剂）的同系化。结果表明，这两种类型的目标化合物都是点击反应的合适底物，因此它们是医药、组合和生物共轭化学的有前途的基石。

  DOI：

  10.1002/ejoc.201701296
• 作为产物：
  描述：

  乙酮,1,1-二环[1.1.1]戊烷-1,3-二基双 在 六氯乙烷 、 三苯基膦 作用下， 以83%的产率得到1,3-Bis(1-chlorvinyl)bicyclo<1.1.1>pentan
  参考文献：
  名称：

  用于点击化学的双环 [1.1.1] 戊烷衍生结构单元

  摘要：

  描述了双环 [1.1.1] 戊烷衍生的叠氮化物和末端炔烃（点击反应的有趣底物）的合成。除了少数例外，标题化合物是从常见的合成中间体 - 相应的羧酸开始，分两步或三步制备的。1-叠氮双环[1.1.1]戊烷合成的关键步骤是铜催化的重氮转移反应与咪唑-1-磺酰叠氮化物。双环[1.1.1] 戊基取代炔烃的制备依赖于 Seyferth-Gilbert 与 1-重氮-2-氧代丙基-膦酸二甲酯（Ohira-Bestmann 试剂）的同系化。结果表明，这两种类型的目标化合物都是点击反应的合适底物，因此它们是医药、组合和生物共轭化学的有前途的基石。

  DOI：

  10.1002/ejoc.201701296

文献信息

• Molecular Rods Combining <i>o</i>-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage
  作者：Jiří Kaleta、Zbyněk Janoušek、Marek Nečas、Ctibor Mazal

  DOI：10.1021/acs.organomet.5b00002

  日期：2015.3.9

  Octacarbonyl dicobalt and bis(dimethyl sulfide)decaborane B10H12(Me2S)2 were successfully added to 1,3-diethynylbicyclo[1.1.1]pentane in good yields. This is an interesting example of a cycloaddition reaction achieved next to the bicyclopentane cage that tends to rearrange in many other cases. It proves that both reagents attack the triple bond in a more or less concerted manner that prevents the rearrangement

  八羰基二钴和双（二甲基硫醚）十硼烷B 10 H 12（Me 2 S）2已成功添加到1,3-二乙炔基双环[1.1.1]戊烷中。这是在双环戊烷笼子旁边实现的环加成反应的一个有趣例子，在许多其他情况下，该笼子倾向于重排。证明了这两种试剂或多或少地协同作用攻击了三键，从而防止了重排。后一反应的产物特别令人感兴趣，因为双环戊烷和邻-碳硼烷的笼子立即以其杆状结构连接。这样就构成了新型的分子转子。1 H和13溶液中的C核磁共振波谱揭示了具有明确定义的几何结构的分子的平均旋转对称性，这在几个示例中已通过X射线结构分析得到了证实。
• Reduction of [1.1.1]propellane with lithium 4,4′-Di-t-butylbiphenyl: Bicyclo[1.1.1]pent-1,3-diyldilithium
  作者：Uwe Bunz、Günter Szeimies

  DOI：10.1016/s0040-4039(00)94592-1

  日期：1990.1
• Synthesis and Structure of Trigonal and Tetragonal Connectors for a “Tinkertoy” Construction Set
  作者：Peter F. H. Schwab、Bruce C. Noll、Josef Michl

  DOI：10.1021/jo020111b

  日期：2002.8.1

  We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with long rigid arms containing 4-pyridyl, 2,2'-bipyridyl, and 2,2'-bipyrimidyl termini, meant to be used as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the termini of 1,3-diethynylbicyclo [1.1.1] pentane was coupled with a brominated aza heterocycle, and second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with 1,2,4,5-tetraiodobenzene. An improved large-scale synthesis for 1,3-diethynylbicyclo[1.1.1]pentane is described. The structures of two of the arms were determined by single-crystal X-ray analysis. Several long molecular rods with 4-pyridyl termini were obtained as byproducts, and a single-crystal X-ray structure is reported for the shortest of these.
• A Triangular Macrocycle Altering Planar and Bulky Sections in Its Molecular Backbone
  作者：Jiří Kaleta、Ctibor Mazal

  DOI：10.1021/ol1031816

  日期：2011.3.18

  A triangular macrocyclic molecule has been synthesized which consists of substituted phenanthrene vertices interconnected by 1,3-diethynylbicyclo[1.1.1]pentane sides. The molecule is the very first example of exploiting the bicyclopentane motif in the construction of a shape persistent macrocycle's backbone. It carries new features such as bulkiness, nonconjugated sigma-bonding, and a certain conformational flexibility due to its easy longitudinal rotation. We have used some of the features in order to rationalize the observed tendency of the compound to form films on various surfaces.
• 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：——