3-Chloro-2,3-dihydro-2-(2-propenyl)-4H-1-benzopyran-4-one | 132541-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Chloro-2,3-dihydro-2-(2-propenyl)-4H-1-benzopyran-4-one
• 英文别名: 3-Chloro-2-prop-2-enyl-2,3-dihydrochromen-4-one；3-chloro-2-prop-2-enyl-2,3-dihydrochromen-4-one
• CAS: 132541-16-3
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: QLFTZEMQUUPOTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-t-butyldimethylsiloxy-1-benzopyrilium triflate 在 2,6-二甲基吡啶 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-Chloro-2,3-dihydro-2-(2-propenyl)-4H-1-benzopyran-4-one
  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

文献信息

• Tandem reactions in 4-siloxy-1-benzopyrylium salts: introduction of substituents and cyclohexene and cyclopentane annulation in chromones
  作者：Yong Gyun Lee、Kenji Ishimaru、Hideharu Iwasaki、Katsuo Ohkata、Kinya Akiba

  DOI：10.1021/jo00006a018

  日期：1991.3

  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.