Ethyl 7-cyano-6-ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-2-carboxylate | 194344-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环庚吡喃类
• 英文名称: Ethyl 7-cyano-6-ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-2-carboxylate
• 英文别名: ethyl 7-cyano-6-ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-2-carboxylate
• CAS: 194344-20-2
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: JDXGFMUACQNJKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 7-cyano-6-ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-2-carboxylate 在 磷酸 作用下， 以95%的产率得到6-Ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-7-carbonitrile
  参考文献：
  名称：

  Synthesis, Reactions, and Structure of 5-Cyano-4-ethoxy-1-ethoxycarbonyl-2-methylazuleno[1,8-b,c]pyran

  摘要：

  AbstractBicyclic azulene compounds, ethyl 4‐(cyanoethoxycarbonylmethyl)‐2‐methylazulene‐1‐carboxylate (2) and ethyl 4‐(cyanoethoxycarbonylmethyl)azulene‐1‐carboxylate (3) were prepared from ethyl 4‐chloro‐2‐methylazulene‐1‐carboxylate (7) and ethyl 4‐ethoxyazulene‐1‐carboxylate (8), respectively. Oxidation of 2 with DDQ gave the title compound, 5‐cyano‐4‐ethoxy‐1‐ethoxycarbonyl‐2‐methylazuleno[1,8‐b,c]pyran (1) and a minor compound, ethyl 4‐cyanomethyl‐2‐methylazulene‐1‐carboxylate (9). Oxidation of 3 by DDQ produced only ethyl 4‐cyanomethylazulene‐1‐carboxylate (10), Reaction of 1 with 100% H3PO4 at room temperature and 100 °C gave 5‐cyano‐4‐ethoxy‐2‐methylazuleno[1,8‐b,c]pyran (11) and 2‐methyl‐4,5‐dihydrozuleno[1,8‐b,c]pyran‐4‐one (12), respectively. All the new compounds were characterized by IR, UV‐vis, NMR and Mass spectra, and the structure of 1 was determined by X‐ray crystallography. Crystal data for 1; space group P21/n, a = 7.391(1), b = 9.660(5), c = 22.859(1) Å, B = 97.01(1)°, V = 1620.0(3) Å3, Z = 4, with final residuals R = 0.047 and Rw = 0.055.

  DOI：

  10.1002/jccs.199700041
• 作为产物：
  描述：

  ethyl 4-chloro-2-methylazulene-1-carboxylate 在 sodium ethanolate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 Ethyl 7-cyano-6-ethoxy-3-methyl-5-oxatricyclo[6.4.1.04,13]trideca-1(12),2,4(13),6,8,10-hexaene-2-carboxylate
  参考文献：
  名称：

  Synthesis, Reactions, and Structure of 5-Cyano-4-ethoxy-1-ethoxycarbonyl-2-methylazuleno[1,8-b,c]pyran

  摘要：

  AbstractBicyclic azulene compounds, ethyl 4‐(cyanoethoxycarbonylmethyl)‐2‐methylazulene‐1‐carboxylate (2) and ethyl 4‐(cyanoethoxycarbonylmethyl)azulene‐1‐carboxylate (3) were prepared from ethyl 4‐chloro‐2‐methylazulene‐1‐carboxylate (7) and ethyl 4‐ethoxyazulene‐1‐carboxylate (8), respectively. Oxidation of 2 with DDQ gave the title compound, 5‐cyano‐4‐ethoxy‐1‐ethoxycarbonyl‐2‐methylazuleno[1,8‐b,c]pyran (1) and a minor compound, ethyl 4‐cyanomethyl‐2‐methylazulene‐1‐carboxylate (9). Oxidation of 3 by DDQ produced only ethyl 4‐cyanomethylazulene‐1‐carboxylate (10), Reaction of 1 with 100% H3PO4 at room temperature and 100 °C gave 5‐cyano‐4‐ethoxy‐2‐methylazuleno[1,8‐b,c]pyran (11) and 2‐methyl‐4,5‐dihydrozuleno[1,8‐b,c]pyran‐4‐one (12), respectively. All the new compounds were characterized by IR, UV‐vis, NMR and Mass spectra, and the structure of 1 was determined by X‐ray crystallography. Crystal data for 1; space group P21/n, a = 7.391(1), b = 9.660(5), c = 22.859(1) Å, B = 97.01(1)°, V = 1620.0(3) Å3, Z = 4, with final residuals R = 0.047 and Rw = 0.055.

  DOI：

  10.1002/jccs.199700041