1,1'-联(双环[1.1.1]戊烷)-3-甲酰氯 | 145143-26-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 1,1'-联(双环[1.1.1]戊烷)-3-甲酰氯
• 英文名称: <2>staffane-3-carboxylic acid chloride
• 英文别名: <2>staffane-3-carbonyl chloride；[1,1'-Bi(bicyclo[1.1.1]pentane)]-3-carbonyl chloride；3-(1-bicyclo[1.1.1]pentanyl)bicyclo[1.1.1]pentane-1-carbonyl chloride
• CAS: 145143-26-6
• 化学式: C₁₁H₁₃ClO
• 分子量: 196.677
• InChiKey: WWCMYKNTMNWNPF-UHFFFAOYSA-N

物化性质

• 沸点：
  235.0±9.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1'-联(双环[1.1.1]戊烷)-3-甲酰氯 在 盐酸 、 sodium azide 、 苄基三乙基氯化铵 作用下， 以 苯 为溶剂， 反应 7.0h， 生成 3-amino<2>staffane hydrochloride
  参考文献：
  名称：

  [n]Staffanes with Terminal Nitrile and Isonitrile Functionalities and Their Metal Complexes

  摘要：

  报道了第一和第二个[n]茚烷的几种桥头腈和异腈衍生物的合成。两种异腈都被转化为五羰基钼配合物。[2]茚烷-3-腈被转化为一种与醋酸二钿形成的配合物，并通过单晶X射线分析进行了表征。

  DOI：

  10.1135/cccc19930089
• 作为产物：
  描述：

  <2>staffane-3-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成 1,1'-联(双环[1.1.1]戊烷)-3-甲酰氯
  参考文献：
  名称：

  [n]Staffanes with Terminal Nitrile and Isonitrile Functionalities and Their Metal Complexes

  摘要：

  报道了第一和第二个[n]茚烷的几种桥头腈和异腈衍生物的合成。两种异腈都被转化为五羰基钼配合物。[2]茚烷-3-腈被转化为一种与醋酸二钿形成的配合物，并通过单晶X射线分析进行了表征。

  DOI：

  10.1135/cccc19930089

文献信息

• Long-range spin density propagation in saturated hydrocarbons: 3-[n]staffyl radicals
  作者：Allan J. McKinley、Prabha N. Ibrahim、V. Balaji、Josef Michl

  DOI：10.1021/ja00052a070

  日期：1992.12

  The bridgehead radicals derived from the first three [n]staffanes (n = 1-3), oligomers of [1.1.1]propellane, have been generated from the corresponding bromides, and their solution EPR spectra have been recorded. Remarkably long-range hyperfine coupling has been found to epsilon, zeta, and even iota hydrogens, in qualitative agreement with ab initio UHF calculations. The coupling to the bridgehead hydrogen is attenuated by a factor of about 25 per added bicyclo[1.1.1]pentane cage. The long-range propagation of spin density can be attributed to strong interaction between the orbitals used to make the exocyclic bonds in the 1 and 3 positions of each bicyclo[1.1.1]pentane cage. The situation can be understood simply in terms of a linear sigma-hyperconjugated chain of orbitals interacting through resonance integrals whose effective magnitude alternates in an about 1:5 ratio. A more detailed analysis is provided by considering the effect on the spin density of the various types of off-diagonal elements in the UHF Hartree-Fock matrix expressed in terms of maximally spin-paired natural bond orbitals (MSP-NBO). This permits a clean separation of through-space and through-bond interactions as well as further separation of each of these into contributions due to bond delocalization and those due to bond spin polarization.
• [n]Staffanes with Terminal Nitrile and Isonitrile Functionalities and Their Metal Complexes
  作者：Tomasz Janecki、Shu Shi、Piotr Kaszynski、Josef Michl

  DOI：10.1135/cccc19930089

  日期：——

  The synthesis of several bridgehead nitrile and isonitrile derivatives of the first two [n]staffanes, n = 1 and 2, is reported. Both isonitriles were converted into pentacarbonylmolybdenum complexes. [2]Staffane-3-carbonitrile was converted to a complex with rhodium(II) acetate, which was characterized by a single crystal X-ray analysis.

  报道了第一和第二个[n]茚烷的几种桥头腈和异腈衍生物的合成。两种异腈都被转化为五羰基钼配合物。[2]茚烷-3-腈被转化为一种与醋酸二钿形成的配合物，并通过单晶X射线分析进行了表征。