5,5-dihydrodicyclohepta[b,d]furan-5a-ol | 1300675-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5,5-dihydrodicyclohepta[b,d]furan-5a-ol
• 英文别名: 9-Oxatricyclo[8.5.0.02,8]pentadeca-1,3,5,10,12,14-hexaen-8-ol；9-oxatricyclo[8.5.0.02,8]pentadeca-1,3,5,10,12,14-hexaen-8-ol
• CAS: 1300675-47-1
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: KOSJHKDGVJNIPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [(1,3-bis((di-tert-butylphosphino)methyl)benzene(-1H))IrH2] 、 环庚三烯酮 在 降冰片烯 作用下， 以 p-xylene-d10 为溶剂， 反应 3.0h， 以32%的产率得到5,5-dihydrodicyclohepta[b,d]furan-5a-ol
  参考文献：
  名称：

  Dehydrogenation of ketones by pincer-ligated iridium: Formation and reactivity of novel enone complexes

  摘要：

  The transfer dehydrogenation of several ketones by (PCP)IrH2 (PCP = kappa(3)-C6H3-2,6-((CH2PBu2)-Bu-t)(2)) (1) has been observed. Catalytic turnover was inhibited in most cases by the formation of stable metallacycles or the O-H oxidative addition of phenolic products. Catalytic transfer dehydrogenation of 3,3-dimethylcyclohexanone was achieved, giving the corresponding alpha,beta-enone. The transfer dehydrogenation reaction of cycloheptanone with 1 was found to generate a surprisingly stable PCP-iridium troponyl hydride (9), which is stabilized by conjugation and possibly represents an unusual bicyclo[5.2.0] troponyliridium metalloaromatic structure. Complex 9 was found to catalyze the dimerization of tropone to give a fused tricyclic dihydrodicycloheptafuranol. A mechanism for this reaction is proposed wherein the coordinated troponyl group nucleophilically attacks a free tropone molecule. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.11.016

文献信息

• Dehydrogenation of ketones by pincer-ligated iridium: Formation and reactivity of novel enone complexes
  作者：Xiawei Zhang、David Y. Wang、Thomas J. Emge、Alan S. Goldman

  DOI：10.1016/j.ica.2010.11.016

  日期：2011.4

  The transfer dehydrogenation of several ketones by (PCP)IrH2 (PCP = kappa(3)-C6H3-2,6-((CH2PBu2)-Bu-t)(2)) (1) has been observed. Catalytic turnover was inhibited in most cases by the formation of stable metallacycles or the O-H oxidative addition of phenolic products. Catalytic transfer dehydrogenation of 3,3-dimethylcyclohexanone was achieved, giving the corresponding alpha,beta-enone. The transfer dehydrogenation reaction of cycloheptanone with 1 was found to generate a surprisingly stable PCP-iridium troponyl hydride (9), which is stabilized by conjugation and possibly represents an unusual bicyclo[5.2.0] troponyliridium metalloaromatic structure. Complex 9 was found to catalyze the dimerization of tropone to give a fused tricyclic dihydrodicycloheptafuranol. A mechanism for this reaction is proposed wherein the coordinated troponyl group nucleophilically attacks a free tropone molecule. (C) 2010 Elsevier B. V. All rights reserved.