20,20-dimethyl-2-oxahexacyclo[15.4.0.0(3,16).1(4,8).2(4(8),11).2(4(8),15)]tricosane-1(17),3(16),4(22),5,7,9,11,13,15(23)-nonaen-18-one | 1240509-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 20,20-dimethyl-2-oxahexacyclo[15.4.0.0(3,16).1(4,8).2(4(8),11).2(4(8),15)]tricosane-1(17),3(16),4(22),5,7,9,11,13,15(23)-nonaen-18-one
• 英文别名: 17,17-Dimethyl-20-oxahexacyclo[10.9.2.05,22.08,23.013,21.014,19]tricosa-1,3,5(22),6,8(23),9,11,13(21),14(19)-nonaen-15-one；17,17-dimethyl-20-oxahexacyclo[10.9.2.05,22.08,23.013,21.014,19]tricosa-1,3,5(22),6,8(23),9,11,13(21),14(19)-nonaen-15-one
• CAS: 1240509-55-0
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: RRXVRAKEZDAUCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,5-二甲基-2-环己烯-1-酮 、 芘-4,5-二酮 在 四氯化钛 、 甲烷磺酸 作用下， 以 二氯甲烷 、 1,1-二氯乙烷 为溶剂， 反应 49.0h， 生成 20,20-dimethyl-2-oxahexacyclo[15.4.0.0(3,16).1(4,8).2(4(8),11).2(4(8),15)]tricosane-1(17),3(16),4(22),5,7,9,11,13,15(23)-nonaen-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