2-hydroxy-2-(5,5-dimethylcyclohex-2-enon-2-yl)-2H-acenaphthylen-1-one | 1240509-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-2-(5,5-dimethylcyclohex-2-enon-2-yl)-2H-acenaphthylen-1-one
• CAS: 1240509-39-0
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: WDWGDSFPMPHUIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-(5,5-dimethylcyclohex-2-enon-2-yl)-2H-acenaphthylen-1-one 在 甲烷磺酸 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 1.0h， 以58%的产率得到{16,16,25,25-tetramethyl-2-oxaheptacyclo[20.4.0.0(3,21).0(4,13).0(8,13).0(12,13).0(14,19)]hexacosane-1(22),4,6,8(13),9,11,14(19)-heptaen-18,23-dione}-20-spiro-1'-acenaphthylen-2'-one
  参考文献：
  名称：

  Toward understanding the scope of Baylis–Hillman reaction: synthesis of 3-(2- hydroxyphenyl)indolin-2-ones and polycyclic fused furans

  摘要：

  A facile one-pot synthesis of 3-(2-hydroxyphenyl)indolin-2-ones has been developed via the TiCl4-mediated Baylis-Hillman (B-H) reaction of N-substituted isatins and cyclohex-2-enone, followed by treatment of the in situ generated B H alcohols with aq HBr. Baylis-Hillman reaction of aromatic cyclic 1,2-diones with cycloalk-2-enones under the influence of TiCl4 has been successfully performed and the resulting Baylis-Hillman adducts have been conveniently transformed into pentacyclic and hexacyclic fused furan derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.087
• 作为产物：
  描述：

  5,5-二甲基-2-环己烯-1-酮 、 苊醌 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到2-hydroxy-2-(5,5-dimethylcyclohex-2-enon-2-yl)-2H-acenaphthylen-1-one
  参考文献：
  名称：

  Toward understanding the scope of Baylis–Hillman reaction: synthesis of 3-(2- hydroxyphenyl)indolin-2-ones and polycyclic fused furans

  摘要：

  A facile one-pot synthesis of 3-(2-hydroxyphenyl)indolin-2-ones has been developed via the TiCl4-mediated Baylis-Hillman (B-H) reaction of N-substituted isatins and cyclohex-2-enone, followed by treatment of the in situ generated B H alcohols with aq HBr. Baylis-Hillman reaction of aromatic cyclic 1,2-diones with cycloalk-2-enones under the influence of TiCl4 has been successfully performed and the resulting Baylis-Hillman adducts have been conveniently transformed into pentacyclic and hexacyclic fused furan derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.087