7-三氟乙酰氨基-3,4-二氢香豆素 | 103515-26-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 中文名称: 7-三氟乙酰氨基-3,4-二氢香豆素
• 英文名称: 7-trifluoroacetamido-3,4-dihydrocoumarin
• 英文别名: 2,2,2-trifluoro-N-(2-oxochroman-7-yl)acetamide；2,2,2-trifluoro-N-(2-oxo-3,4-dihydrochromen-7-yl)acetamide
• CAS: 103515-26-0
• 化学式: C₁₁H₈F₃NO₃
• 分子量: 259.185
• InChiKey: WEEUCQHAWLLUBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-三氟乙酰氨基-3,4-二氢香豆素 在 吡啶 、 咪唑 、 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (3aR,5R,6aS)-4-[(E)-(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-4-(trityl-amino)-phenyl]-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
  参考文献：
  名称：

  Utilization of a nitrenium ion cyclization in a synthesis of a photoactive prostaglandin, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2/ga

  摘要：

  DOI：

  10.1016/s0040-4039(00)95644-2
• 作为产物：
  描述：

  对硝基肉桂酸 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 三氟乙酸 、 sodium nitrite 作用下， 生成 7-三氟乙酰氨基-3,4-二氢香豆素
  参考文献：
  名称：

  Utilization of a nitrenium ion cyclization in a synthesis of a photoactive prostaglandin, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2/ga

  摘要：

  DOI：

  10.1016/s0040-4039(00)95644-2

文献信息

• Remote intramolecular functionalization of arylnitrenium ions. ipso-substitution and spiro-lactone formation
  作者：Rudolph A. Abramovitch、Amale Hawi、J. Augusto R. Rodrigues、Tania R. Trombetta

  DOI：10.1039/c39860000283

  日期：——

  Acid-catalysed decomposition of (4′-azidophenyl)propanoic and butyric acids leads to ipso-attack by the carboxy group para to the nitrenium ion and the formation of imines of cyclohexadienone spiro-lactones, which can rearrange to the benz-fused lactones; 4′-azido-2-carboxydiphenyl ether behaves the same way to give spiro-lactone (9).

  的（4'-叠氮基苯基）丙酸和丁酸导致酸催化分解本位由羧基-attack对位到nitrenium离子并形成环己二烯酮螺内酯的亚胺，其可以重新排列到苯并稠合的内酯; 4'-叠氮基-2-羧基二苯醚的行为与生成螺内酯的方法相同（9）。
• Prostaglandin photoaffinity probes: synthesis and biological activity of azide-substituted 16-phenoxy- and 17-phenyl-PGF2.alpha. prostaglandins
  作者：Kenji Kawada、E. Kurt Dolence、Hiroyuki Morita、Tadashi Kometani、David S. Watt、Anil Balapure、Tony A. Fitz、David J. Orlicky、L. E. Gerschenson

  DOI：10.1021/jm00121a046

  日期：1989.1

  The development of a prostaglandin PGF2 alpha photoaffinity probe led to the synthesis and biological evaluation of azide-substituted 17-phenyl-18,19,20-trinorprostaglandin F2 alpha and 16-phenoxy-17,18,19,20-tetranorprostaglandin F2 alpha derivatives. Two approaches for the preparation of iodinated versions of these prostaglandins were evaluated: (1) iodination of a phenyl azide bearing an activating hydroxyl group and (2) iodination of an aniline precursor to the phenyl azide group and subsequent conversion of the aniline to the phenyl azide. In the first approach, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2 alpha, 16-(5-azido-3-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2 alpha, and 16-(4-azido-2-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2 alpha were prepared by using the Corey synthesis, but were biologically inactive presumably as a result of the hydrophilic phenolic hydroxyl group. In the second approach, the iodination of a 17-(4-aminophenyl)-18,19,20-trinorprostaglandin F2 alpha derivative delivered 17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2 alpha, which exhibited competitive binding with natural [3H]PGF2 alpha to ovine luteal cells and to plasma membranes of bovine corpora lutea. [125I]-17-(4-Azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2 alpha was utilized in a preliminary photoaffinity cross-linking experiment.
• ABRAMOVITCH, R. A.;HAWI, A.;RODRIGUES, J. A. R.;TROMBETTA, T. R., J. CHEM. SOC. CHEM. COMMUN., 1986, N 4, 283-284
  作者：ABRAMOVITCH, R. A.、HAWI, A.、RODRIGUES, J. A. R.、TROMBETTA, T. R.

  DOI：——

  日期：——
• Utilization of a nitrenium ion cyclization in a synthesis of a photoactive prostaglandin, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2/ga
  作者：E.Kurt Dolence、Hiroyuki Morita、David S. Watt、Tony Fitz

  DOI：10.1016/s0040-4039(00)95644-2

  日期：1987.1