ethyl 4-ethoxyazulene-1-carboxylate | 128637-49-0

• 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-ethoxyazulene-1-carboxylate
• CAS: 128637-49-0
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: BFXSZFZGJNGQQK-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  370.8±15.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-ethoxyazulene-1-carboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到ethyl 4-hydrazinylazulene-1-carboxylate
  参考文献：
  名称：

  3 H -azuleno [8,1- cd ]哒嗪的高效合成及其热化学反应

  摘要：

  通过对甲苯磺酸催化的亚胺形成和分子内环化，然后使用KOH / MeOH脱氢进行一锅操作，由4-肼基azulene -1-羧酸乙酯（2）有效地合成了Azulenopyridazines 6。ule嗪并哒嗪6的热和光化学反应以良好的产率提供了1-乙烯基az嗪7。

  DOI：

  10.1016/j.tetlet.2010.07.007
• 作为产物：
  描述：

  ethyl 8-hydroxy-2-oxo-2H-cycloheptafuran-3-carboxylate 、 二甲氧基乙烷 以33%的产率得到
  参考文献：
  名称：

  NOZOE, TETSUO;WAKABAYASHI, HIDETSUGU;ISHIKAWA, SUMIO;WU, CHI-PHI;YANG, PA+, HETEROCYCLES, 31,(1990) N, C. 17-22

  摘要：

  DOI：

文献信息

• Synthesis, characterization and applications of densely functionalized pyridazines and fulvene-type compounds containing azulene moiety
  作者：Badugu Devendar、Chi-Phi Wu、Chi-Yuan Chen、Hung-Chang Chen、Chung-Hao Chang、Chien-Kuo Ku、Cheng-Yin Tsai、Chieh-Yuan Ku

  DOI：10.1016/j.tet.2013.04.034

  日期：2013.6

  Ethyl 4-ethoxyazulene-1-carboxylate (1) is highly efficient and novel substrate for electrophilic substitution reactions. These derivatives (2–4) were treated with NH2NH2/PhNHNH2 in ethanol to produce pyridazine, and fulvene derivatives with azulene frameworks (5, 6, 17, 19) via intramolecular cyclization. The substrates 5–8, 11, and 19 were effectively converted into densely functionalized heterocyclic

  4-乙氧基氮杂-1-羧酸乙酯（1）是高效且新颖的用于亲电取代反应的底物。这些衍生物（2 - 4）用NH处理2 NH 2 / PhNHNH 2在乙醇中，以产生哒嗪，并用薁框架富烯衍生物（5，6，17，19）通过分子内环化。基板5 - 8，11，和19 通过Vilsmeier-Haack，Friedel-Crafts和Michael加成反应被有效地转化为稠密官能化的杂环分子。
• 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。
• Nozoe, Tetsuo; Wakabayashi, Hidetsugu; Ishikawa, Sumio, Heterocycles, 1990, vol. 31, # 1, p. 17 - 22
  作者：Nozoe, Tetsuo、Wakabayashi, Hidetsugu、Ishikawa, Sumio、Wu, Chi-Phi、Yang, Paw-Wang

  DOI：——

  日期：——
• 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.
• Efficient syntheses of 3H-azuleno[8,1-cd]pyridazines and their thermal and photochemical reactions
  作者：Chi-Phi Wu、Rammohan Devulapally、Tsung-Chieh Li、Chien-Kuo Ku、Hsien-Chung Chung

  DOI：10.1016/j.tetlet.2010.07.007

  日期：2010.9

  4-hydrazinylazulene-1-carboxylate (2) by p-toluenesulfonic acid-catalyzed imine formation and intramolecular cyclization followed by dehydrogenation using KOH/MeOH in one-pot operation. Thermal and photochemical reactions of azulenopyridazines 6 afforded 1-vinylazulenes 7 in good yields.

  通过对甲苯磺酸催化的亚胺形成和分子内环化，然后使用KOH / MeOH脱氢进行一锅操作，由4-肼基azulene -1-羧酸乙酯（2）有效地合成了Azulenopyridazines 6。ule嗪并哒嗪6的热和光化学反应以良好的产率提供了1-乙烯基az嗪7。