5-methoxy-6,6-diphenylhexanal | 945266-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methoxy-6,6-diphenylhexanal
• CAS: 945266-14-8
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: WLRGXXOAHHBYBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-6,6-diphenylhexanal 在 4 A molecular sieve 、 N-methylquinolinium hexafluorophosphate N-甲基咪唑 、 air 、 sodium acetate 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 sodium thiosulfate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (4aRS,9aSR)-hexahydro-6-methoxy-4H-[1,3]dioxino[5,4-b]oxepin-2-one
  参考文献：
  名称：

  An Experimental and Computational Approach to Defining Structure/Reactivity Relationships for Intramolecular Addition Reactions to Bicyclic Epoxonium Ions

  摘要：

  In this manuscript we report that oxidative cleavage reactions can be used to form oxocarbenium ions that react with pendent epoxides to form bicyclic epoxonium ions as an entry to the formation of cyclic oligoether compounds. Bicyclic epoxonium ion structure was shown to have a dramatic impact on the ratio of exo- to endo-cyclization reactions, with bicyclo[4.1.0] intermediates showing a strong preference for endo-closures and bicyclo[3.1.0] intermediates showing a preference for exo-closures. Computational studies on the structures and energetics of the transition states using the B3LYP/6-31G(d) method provide substantial insight into the origins of this selectivity.

  DOI：

  10.1021/ja0709674
• 作为产物：
  描述：

  二苯基甲烷 在 正丁基锂 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-6,6-diphenylhexanal
  参考文献：
  名称：

  An Experimental and Computational Approach to Defining Structure/Reactivity Relationships for Intramolecular Addition Reactions to Bicyclic Epoxonium Ions

  摘要：

  In this manuscript we report that oxidative cleavage reactions can be used to form oxocarbenium ions that react with pendent epoxides to form bicyclic epoxonium ions as an entry to the formation of cyclic oligoether compounds. Bicyclic epoxonium ion structure was shown to have a dramatic impact on the ratio of exo- to endo-cyclization reactions, with bicyclo[4.1.0] intermediates showing a strong preference for endo-closures and bicyclo[3.1.0] intermediates showing a preference for exo-closures. Computational studies on the structures and energetics of the transition states using the B3LYP/6-31G(d) method provide substantial insight into the origins of this selectivity.

  DOI：

  10.1021/ja0709674