| 122130-13-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• CAS: 122130-13-6；132541-17-4；132541-18-5
• 化学式: C₂₅H₃₀O₃Si
• 分子量: 406.597
• InChiKey: FTLPWLWFAPCXQW-MZYLBHOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到1,2,3,4,4a,9a-Hexahydro-1-phenyl-9H-xanthen-3,9-dione
  参考文献：
  名称：

  Tandem reactions in 4-siloxy-1-benzopyrylium salts: introduction of substituents and cyclohexene and cyclopentane annulation in chromones

  摘要：

  Reactions of 4-[(tert-butyldimethylsilyl)oxy]-1-benzopyrylium triflates (2a-c) with silyl enol ethers (3a-d) or allyl organometallic reagents (5a-c) afforded the corresponding 2-substituted 4-siloxy-2H-1-benzopyrans (4a-d and 6a-d) along with 2,3-dihydrobenzopyrone derivatives (7a-c). An unexpected cyclopentane annulation to give 8a,b was observed in the reaction of 2a,b with 3-(trimethylsilyl)-1-butene (5d). Treatment of the products (4a and 6a) with electrophiles (iminium salt, NBS, and NCS) converted them into the corresponding 2,3-disubstituted 2,3-dihydrobenzopyrone derivatives (9a-c). Reaction of benzopyrylium salts (2a,b) with alpha,beta-unsaturated ketones (10a-g) in the presence of tert-butyldimethylsilyl triflate and 2,6-lutidine gave cyclohexene annulation products (xanthone derivatives, 11a-j) in moderate to high yield. The reaction mechanisms are explained in terms of stereoelectronic and 1,3-allylic strain effects together with steric hindrance during the reaction.

  DOI：

  10.1021/jo00006a018
• 作为产物：
  描述：

  色酮 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Tandem reactions in 4-siloxy-1-benzopyrylium salts: introduction of substituents and cyclohexene and cyclopentane annulation in chromones

  摘要：

  Reactions of 4-[(tert-butyldimethylsilyl)oxy]-1-benzopyrylium triflates (2a-c) with silyl enol ethers (3a-d) or allyl organometallic reagents (5a-c) afforded the corresponding 2-substituted 4-siloxy-2H-1-benzopyrans (4a-d and 6a-d) along with 2,3-dihydrobenzopyrone derivatives (7a-c). An unexpected cyclopentane annulation to give 8a,b was observed in the reaction of 2a,b with 3-(trimethylsilyl)-1-butene (5d). Treatment of the products (4a and 6a) with electrophiles (iminium salt, NBS, and NCS) converted them into the corresponding 2,3-disubstituted 2,3-dihydrobenzopyrone derivatives (9a-c). Reaction of benzopyrylium salts (2a,b) with alpha,beta-unsaturated ketones (10a-g) in the presence of tert-butyldimethylsilyl triflate and 2,6-lutidine gave cyclohexene annulation products (xanthone derivatives, 11a-j) in moderate to high yield. The reaction mechanisms are explained in terms of stereoelectronic and 1,3-allylic strain effects together with steric hindrance during the reaction.

  DOI：

  10.1021/jo00006a018