Ethyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-2-methylazulene-1-carboxylate | 194344-21-3

• 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 4-(1-cyano-2-ethoxy-2-oxoethyl)-2-methylazulene-1-carboxylate
• 英文别名: ethyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-2-methylazulene-1-carboxylate
• CAS: 194344-21-3
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: XJSQKNVVUGUAQP-UHFFFAOYSA-N

物化性质

• 沸点：
  476.3±40.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-2-methylazulene-1-carboxylate 在 磷酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 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：

  氰乙酸乙酯 、 ethyl 4-chloro-2-methylazulene-1-carboxylate 在 sodium ethanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到Ethyl 4-(1-cyano-2-ethoxy-2-oxoethyl)-2-methylazulene-1-carboxylate
  参考文献：
  名称：

  稠密官能化的环戊环[cd] azulenes和环戊环[ef]庚烯的简便合成方法

  摘要：

  新颖环戊二烯并[的合成CD ]薁，5,8，和13，1,2-二氢环戊二烯并[ CD ]薁，6和12，并环戊二烯并[ EF ] heptalenes，10，15，和16，通过从开始托酚酮简单的程序描述了6-8个步骤。

  DOI：

  10.1002/hlca.201300192

文献信息

• A Convenient and Simple Synthesis of Densely Functionalized Cyclopenta[<i>cd</i>]azulenes and Cyclopenta[<i>ef</i>]heptalenes
  作者：Badugu Devendar、Chien-Kuo Ku、Ling-Yu Cheng、Shu-Juan Yang、Jun-Xiong Chen、Chi-Phi Wu

  DOI：10.1002/hlca.201300192

  日期：2014.4

  Syntheses of novel cyclopenta[cd]azulenes, 5, 8, and 13, 1,2‐dihydrocyclopenta[cd]azulenes, 6 and 12, and cyclopenta[ef]heptalenes, 10, 15, and 16, by simple procedures starting from tropolone in 6–8 steps are described.

  新颖环戊二烯并[的合成CD ]薁，5,8，和13，1,2-二氢环戊二烯并[ CD ]薁，6和12，并环戊二烯并[ EF ] heptalenes，10，15，和16，通过从开始托酚酮简单的程序描述了6-8个步骤。
• Synthesis, Reactions, and Structure of 5-Cyano-4-ethoxy-1-ethoxycarbonyl-2-methylazuleno[1,8-b,c]pyran
  作者：Chi-Phi Wu、Ling-Yu Cheng、Yuh-Sheng Wen、Chwan-Deng Hsiao

  DOI：10.1002/jccs.199700041

  日期：1997.6

  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.