p-fluorophenyl (2E)-4-hydroxy-2-butenoate | 163457-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-fluorophenyl (2E)-4-hydroxy-2-butenoate
• 英文别名: 2-Butenoic acid, 4-hydroxy-, 4-fluorophenyl ester, (E)-；(4-fluorophenyl) (E)-4-hydroxybut-2-enoate
• CAS: 163457-40-7
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: UCZBPOSEGTVLFH-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-fluorophenyl (2E)-4-hydroxy-2-butenoate 在 4-二甲氨基吡啶 、 四溴化碳 、 水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 27.5h， 生成 (-)-p-fluorophenyl (2E)-4-<((2'R)-2'-(bromomethyl)butanoyl)oxy>-2-butenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  (E)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enoic acid 4-fluoro-phenyl ester 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以90%的产率得到p-fluorophenyl (2E)-4-hydroxy-2-butenoate
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e

文献信息

• Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis
  作者：Masataka Ihara、Akira Katsumata、Fumihito Setsu、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo951653e

  日期：1996.1.1

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.