| 144018-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 144018-24-6
• 化学式: C₁₀H₁₈Cl₅OSb
• 分子量: 453.267
• InChiKey: GOFPVOAJFOYBGW-UHFFFAOYSA-I

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  3,3,5,5-四甲基环己酮 、 氯化锑(V) 以 一氟三氯甲烷 、 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 生成
  参考文献：
  名称：

  Crystal structures of two activated cyclohexanones with opposite pyramidalizations of the carbonyl groups

  摘要：

  The crystal structure analyses of the two 3,3,5,5-tetraalkylcyclohexanones 1 and 2 activated by Li+ or SbCl5 complexation show that 1 and 2 have rather different chair conformations and opposite pyramidalizations of the carbonyl group. The bicyclic ketone 1 has an exocyclic C=C double bond acting as an intramolecular nucleophile attacking the carbonyl group from the axial direction, whereas 2 is preferentially attacked by nucleophiles from the equatorial direction. In 1, the axial a protons (but not the C(alpha)-C(beta) bonds) are well aligned for hyperconjugative interactions with the carbonyl group, whereas, in 2, both the axial C(alpha)-H and the C(alpha)-C(beta) bonds may interact with the carbonyl group. In all structures, a C=O elongation and a C(C=O)-C(alpha) shortening are observed. In addition, 2 shows a slight C(alpha)-C(beta) elongation. The conformational differences between 1 and 2 are in agreement with the general conformational flexibility of cyclohexanones, as could be shown by comparison of their Cremer-Pople puckering parameters with those of cyclohexanones from the Cambridge Structural Database. The direction of the carbonyl pyramidalization is compared with that of pyramidalized sp2 C atoms in a norbornenyl cation and discussed in terms of preferential attacks of nucleophiles, as predicted by current models of stereoselective nucleophile addition (Cieplak, Houk, Klein, Felkin).

  DOI：

  10.1021/ja00049a011