ethyl 2-acetylamino-3-trimethylsilylethynylazulene-1-carboxylate | 1454276-31-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: ethyl 2-acetylamino-3-trimethylsilylethynylazulene-1-carboxylate
• 英文别名: Ethyl 2-acetamido-3-(2-trimethylsilylethynyl)azulene-1-carboxylate；ethyl 2-acetamido-3-(2-trimethylsilylethynyl)azulene-1-carboxylate
• CAS: 1454276-31-3
• 化学式: C₂₀H₂₃NO₃Si
• 分子量: 353.493
• InChiKey: AYTXPMZCEZGNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-aminoazulene-1-carboxylate 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.25h， 生成 ethyl 2-acetylamino-3-trimethylsilylethynylazulene-1-carboxylate
  参考文献：
  名称：

  Synthesis, Cyclization, and Evaluation of the Anticancer Activity against HeLa S-3 Cells of Ethyl 2-Acetylamino-3-ethynylazulene-1-carboxylates

  摘要：

  Reaction of ethyl 2-aminoazulene-1-carboxylate with NIS in CHCl3 gave 2,2'-diamino-3,3'-diethoxycarbonyl-1,1'-biazulene (3) and a terazulene derivative. The coupling of azulenes was catalyzed by acid. Operation of the reaction in the presence of Et3N in CH2Cl2 for 7 min at -7 degrees C retarded the coupling of the azulene nuclei to give ethyl 2-amino-3-iodoazulene-1-carboxylate (1a) in 95% yield. Sonogashira cross-coupling of ethyl 2-acetylamino-3-iodoazulene-1-carboxylate (1b) gave ethyl 2-acetylamino-3-ethynylazulene-1-carboxylates (5a and 5b) in good yields. Cyclization of ethyl 2-acetylamino-3-phenylethynylazulene-1-carboxylate with Pd-catalyst gave azuleno[2,1-b]pyrrole derivatives. Compounds (3 and 5b) showed potent cytotoxic activity against HeLa S-3 cells (IC50 [mu M] : 3: 2.9 +/- 0.2,5b: 13.4 +/- 1.1).

  DOI：

  10.3987/com-12-s(n)4

文献信息

• Synthesis, Cyclization, and Evaluation of the Anticancer Activity against HeLa S-3 Cells of Ethyl 2-Acetylamino-3-ethynylazulene-1-carboxylates
  作者：Noritaka Abe、Hajime Nakagawa、Takahiro Gunji、Yoshino Ito、Yu Kawai、Reiko Ikeda、Takeo Konakahara、Marie Hyoudou

  DOI：10.3987/com-12-s(n)4

  日期：——

  Reaction of ethyl 2-aminoazulene-1-carboxylate with NIS in CHCl3 gave 2,2'-diamino-3,3'-diethoxycarbonyl-1,1'-biazulene (3) and a terazulene derivative. The coupling of azulenes was catalyzed by acid. Operation of the reaction in the presence of Et3N in CH2Cl2 for 7 min at -7 degrees C retarded the coupling of the azulene nuclei to give ethyl 2-amino-3-iodoazulene-1-carboxylate (1a) in 95% yield. Sonogashira cross-coupling of ethyl 2-acetylamino-3-iodoazulene-1-carboxylate (1b) gave ethyl 2-acetylamino-3-ethynylazulene-1-carboxylates (5a and 5b) in good yields. Cyclization of ethyl 2-acetylamino-3-phenylethynylazulene-1-carboxylate with Pd-catalyst gave azuleno[2,1-b]pyrrole derivatives. Compounds (3 and 5b) showed potent cytotoxic activity against HeLa S-3 cells (IC50 [mu M] : 3: 2.9 +/- 0.2,5b: 13.4 +/- 1.1).