diethynylgular<3>phenylene | 149826-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: diethynylgular<3>phenylene
• 英文别名: diethynylgular[3]phenylene；10,11-Diethynylpentacyclo[10.6.0.02,9.03,8.013,18]octadeca-1(12),2(9),3,5,7,10,13,15,17-nonaene
• CAS: 149826-87-9
• 化学式: C₂₂H₁₀
• 分子量: 274.321
• InChiKey: CBFBMKOOMAOWOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,6-bis(triisopropylsilyl)-1,3,5-hexatriyne 、 diethynylgular<3>phenylene 在 cyclopentadienyl-biscarbonyl-cobalt(I) 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Boese, Roland; Matzger, Adam J.; Mohler, Debra L., Angewandte Chemie, 1995, vol. 107, # 13/14, p. 1630 - 1633

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-bis[(trimethylsilyl)ethynyl] angular [3]phenylene 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 diethynylgular<3>phenylene
  参考文献：
  名称：

  Boese, Roland; Matzger, Adam J.; Mohler, Debra L., Angewandte Chemie, 1995, vol. 107, # 13/14, p. 1630 - 1633

  摘要：

  DOI：

文献信息

• Synthesis, structure, and dynamics of endo-(starphenylene)chromium tricarbonyl derivatives: observation of metal-arene migration and hindered metal-tripod rotation
  作者：Mitch Nambu、Debra L. Mohler、Kenneth Hardcastle、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1021/ja00067a032

  日期：1993.7

  The dynamic stereochemistry of endo-(starphenylene)chromium tricarbonyl, enro-1-Cr, is elucidated through NMR spectroscopic methods. Intramolecular metal-arene migration and hindered metal-tripod rotation are observed in closely related derivatives of enro-1-Cr. The stereochemistry of these systems is modeled well by ab initio local density functional theory methods

  内-（星形亚苯基）三羰基铬，enro-1-Cr 的动态立体化学是通过核磁共振光谱方法阐明的。在密切相关的 enro-1-Cr 衍生物中观察到分子内金属-芳烃迁移和受阻金属-三脚架旋转。这些系统的立体化学通过 ab initio 局部密度泛函理论方法很好地建模
• On the Nature of Nonplanarity in the [N]Phenylenes
  作者：Daniel Holmes、Sriram Kumaraswamy、Adam J. Matzger、K. Peter C. Vollhardt

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3399::aid-chem3399>3.0.co;2-v

  日期：1999.11.5

  The [N]phenylenes display marked deformation from planarity in the crystalline state. In order to probe the generality of this phenomenon, several derivatives were synthesized and their single-crystal X-ray structures were obtained. All new compounds displayed some degree of nonplanarity. Thus, for example, the parent triangular [4]phenylene (4b) has a median bend angle at the ring junction of 1.5 degrees and a range of 0.3 degrees to 3.5 degrees, whereas hexakis[triisopropylsilyl(ethynyl)] triangular [4]phenylene (4c) possesses the bulkiest appendages and the largest median bend angle and range (3.8 degrees and 1.7 degrees-5.6 degrees, respectively). A detailed analysis of the bending and twisting angles at the ring junctions, however, revealed that the magnitude of deformations were independent of topology, molecular size, and substituent type. In contrast to the phenylenes, a Cambridge Structural Database (CSD) search of unsubstituted and non-peri-substituted naphthalenes and anthracenes shows these molecules to be virtually planar in the solid state. A comparison of the single-point energies (HF/6-31G*) of the phenylenes with the acenes calculated for molecules possessing a fixed bend angle at the ring fusion of 3 degrees, 6 degrees, 9 degrees, and 12 degrees reveals the former to be 26% to 45% easier to deform than the latter. Based on these results, the nonplanarity seen for the phenylenes is most likely a consequence of crystal-packing forces deforming particularly flexible molecules.