Pentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>tridecan-11-one dimethyl ketal | 132674-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Pentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>tridecan-11-one dimethyl ketal
• 英文别名: Pentacyclo[6.5.0.0^4,12.0^5,10.0^9,13]tridecan-11-one dimethyl ketal；11,11-dimethoxypentacyclo[6.5.0.04,12.05,10.09,13]tridecane
• CAS: 132674-06-7
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: YPMFIKHSIIDGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Pentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>tridecan-11-one dimethyl ketal 在 lithium aluminium tetrahydride 、 amberlyst-15 、 水 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Stereochemistry of nucleophilic addition to several rigid, sterically unbiased 7-norbornanones

  摘要：

  A stereochemical investigation is reported of the reactions of lithium aluminum hydride (LAH) and of methyllithium with three sterically unbiased, rigid ketones: tetracyclo[7.4.0.0(2,7).0(6,10)]trideca-3,12-dien-8-one (2), pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]tridecan-11-one (3), and pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]trideca-2,6-dien-11-one (4). Various proton NMR techniques were brought to bear upon the dual problems of characterization and analysis of the mixtures of epimeric alcohols obtained. The results can be interpreted in terms of transition-state hyperconjugation. A comparison with literature data on other endo-substituted 7-norbornanones points up the need, in studies of electronically controlled face selection, for probes that not only have sterically equivalent faces but are also conformationally rigid.

  DOI：

  10.1021/jo00006a010
• 作为产物：
  描述：

  9,10,12,13-四氯-五环[6.5.0.04,12.05,10.09,13]十三烷-11-酮二甲基缩酮 在 lithium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到Pentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>tridecan-11-one dimethyl ketal
  参考文献：
  名称：

  Stereochemistry of nucleophilic addition to several rigid, sterically unbiased 7-norbornanones

  摘要：

  A stereochemical investigation is reported of the reactions of lithium aluminum hydride (LAH) and of methyllithium with three sterically unbiased, rigid ketones: tetracyclo[7.4.0.0(2,7).0(6,10)]trideca-3,12-dien-8-one (2), pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]tridecan-11-one (3), and pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]trideca-2,6-dien-11-one (4). Various proton NMR techniques were brought to bear upon the dual problems of characterization and analysis of the mixtures of epimeric alcohols obtained. The results can be interpreted in terms of transition-state hyperconjugation. A comparison with literature data on other endo-substituted 7-norbornanones points up the need, in studies of electronically controlled face selection, for probes that not only have sterically equivalent faces but are also conformationally rigid.

  DOI：

  10.1021/jo00006a010

文献信息

• LI, HAIFANG;MEHTA, G.;PADMA, S.;IE, NOBLE W. J., J. ORG. CHEM., 56,(1991) N, C. 2006-2011
  作者：LI, HAIFANG、MEHTA, G.、PADMA, S.、IE, NOBLE W. J.

  DOI：——

  日期：——