20,20-dimethyl-2-oxapentacyclo[15.4.0.0(3,16).0(4,9).0(10,15)]henicosan-1(17),3(16),4(9),5,7,10(15),11,13-octaen-18-one | 1240509-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 20,20-dimethyl-2-oxapentacyclo[15.4.0.0(3,16).0(4,9).0(10,15)]henicosan-1(17),3(16),4(9),5,7,10(15),11,13-octaen-18-one
• CAS: 1240509-52-7
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: UBPOOGOYYCPOMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  10-hydroxy-10-(5,5-dimethylcyclohex-2-enon-2-yl)-10H-phenanthren-9-one 在 甲烷磺酸 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 0.5h， 以89%的产率得到20,20-dimethyl-2-oxapentacyclo[15.4.0.0(3,16).0(4,9).0(10,15)]henicosan-1(17),3(16),4(9),5,7,10(15),11,13-octaen-18-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