ethyl (E)-3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate | 74222-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate
• 英文别名: ethyl (E)-3-(4-methoxynaphthalen-1-yl)-2-nitroprop-2-enoate
• CAS: 74222-06-3
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: BJIZKUKSFQJVRJ-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate 以 丙酮 为溶剂， 反应 2.0h， 以2.8%的产率得到5-Methoxy-naphtho[1,2-b]furan-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Hirotani, Seiko; Zen, Shonosuke, Chemical and pharmaceutical bulletin, 1983, vol. 31, p. 2944 - 2947

  摘要：

  DOI：
• 作为产物：
  描述：

  硝基乙酸乙酯 、 4-甲氧基-1-萘甲醛 生成 ethyl (E)-3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate 、 ethyl (Z)-3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate
  参考文献：
  名称：

  A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride

  摘要：

  Titanium tetrachloride-induced cyclization of 3-(o- or m-substituted p-methoxyphenyl)-2-nitro acrylates (1) provided stereoselectively (4 alpha,5 beta)-1-oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p-methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4 alpha,5 beta)-4'-oxospiro[isoxazole-(4H)5,1'(4'H)-naphthalene]. 3-(10'-methoxy-9'-anthryl)-2-nitroacrylate was converted to 10-oxospiro-[anthracene-(10H)9,5'(4'H)-isoxazole]. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00119-2

文献信息

• A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride
  作者：Seiko Hirotani、Eisuke Kaji

  DOI：10.1016/s0040-4020(99)00119-2

  日期：1999.4

  Titanium tetrachloride-induced cyclization of 3-(o- or m-substituted p-methoxyphenyl)-2-nitro acrylates (1) provided stereoselectively (4 alpha,5 beta)-1-oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p-methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-1'-naphthyl)-2-nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4 alpha,5 beta)-4'-oxospiro[isoxazole-(4H)5,1'(4'H)-naphthalene]. 3-(10'-methoxy-9'-anthryl)-2-nitroacrylate was converted to 10-oxospiro-[anthracene-(10H)9,5'(4'H)-isoxazole]. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hirotani, Seiko; Zen, Shonosuke, Chemical and pharmaceutical bulletin, 1983, vol. 31, p. 2944 - 2947
  作者：Hirotani, Seiko、Zen, Shonosuke

  DOI：——

  日期：——