(Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester | 444890-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester
• 英文别名: (2-but-3-en-1-ynylphenyl) (Z)-3-bromoprop-2-enoate
• CAS: 444890-79-3
• 化学式: C₁₃H₉BrO₂
• 分子量: 277.117
• InChiKey: VFADLHADFVPTDY-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester 、 2-甲基-1-丁烯-3-炔 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以54%的产率得到9-(1-methylvinyl)-10-vinyl-6H-dibenzo[b,d]pyran-6-one
  参考文献：
  名称：

  Synthesis of 6H-Dibenzo[b,d]pyran-6-ones from Aryl 3-Bromopropenoates via a Sequential One-Pot Procedure Using the Sonogashira Coupling−Benzannulation Reaction

  摘要：

  Various kinds of 6H-dibenzo [b,d] pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo [b,d] pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate le, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.

  DOI：

  10.1021/jo025659x
• 作为产物：
  描述：

  o-((trimethylsilyl)ethynyl)phenol 在 四(三苯基膦)钯 甲醇 、 4-二甲氨基吡啶 、 potassium fluoride 、 copper(l) iodide 、 二乙胺 、 2,3-二脱氧胞啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.84h， 生成 (Z)-3-bromopropenoic acid 2-but-3-en-1-ynylphenyl ester
  参考文献：
  名称：

  Synthesis of 6H-Dibenzo[b,d]pyran-6-ones from Aryl 3-Bromopropenoates via a Sequential One-Pot Procedure Using the Sonogashira Coupling−Benzannulation Reaction

  摘要：

  Various kinds of 6H-dibenzo [b,d] pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo [b,d] pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate le, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.

  DOI：

  10.1021/jo025659x