ethyl 4-acetyl-5-methylfuran-2-carboxylate | 29172-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 4-acetyl-5-methylfuran-2-carboxylate
• CAS: 29172-08-5
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: JDPLMMFMBNVBHG-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  303.7±42.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-acetyl-5-methylfuran-2-carboxylate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 硫酸 、 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氯化碳 、 乙醇 、 氯仿 为溶剂， 反应 12.5h， 生成 ethyl 5-hydroxymethyl-4-(1,2,3-thiadiazol-4-yl)-furan-2-carboxylate
  参考文献：
  名称：

  Synthesis of ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and its reactions with nucleophiles

  摘要：

  By cyclization of carboethoxyhydrazone of ethyl 4-acetyl-5-methylfuran-2-carboxylate under the conditions of Hurd-Mori reaction ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate was synthesized. The ester obtained was brominated with N-bromosuccinimide at the methyl group in the furan ring. This bromide reacts with various N-, S-, O-, and P-nucleophiles to form the corresponding substitution products. Furylthiadiazole fragment remains stable in the course of these transformations.

  DOI：

  10.1134/s1070363215120117
• 作为产物：
  描述：

  4-Acetyl-2-(dimethyl-λ⁴-sulfanylidene)-5-oxo-hex-3-enoic acid ethyl ester 以65%的产率得到
  参考文献：
  名称：

  WATANABE MITSUAKI; BABA MITSUKI; KINSOHITA TOSHIO; FURUKAWA SUNAO, CHEM. AND PHARM. BULL, 1976, 24, NO 10, 2421-2427

  摘要：

  DOI：

文献信息

• Synthesis of the Derivatives of 4-(1,2,3-Selenadiazol-4-yl)-5-methyl-2-furoate Functionalyzed at the Methyl Group
  作者：A. G. Mashichev、L. M. Pevzner、M. L. Petrov

  DOI：10.1134/s1070363220120427

  日期：2020.12

  2,3-selenadiazol-4-yl)-5-methyl-2-furoate was synthesized. It was established, that when treated with N-bromosuccinimide this compound decomposes. That is why for preparing its derivatives functionalized at the methyl group the substituent desired must be introduced before the formation of selenadiazole ring. By this way corresponding phosphonate and a series of phenyl ethers were syhthesized.

  摘要 通过用二氧化硒处理4-乙酰基-5-甲基-2-糠酸乙酯，合成了4-（1,2,3-硒代重氮-4-基）-5-甲基-2-糠酸乙酯。已经确定，当用N-溴琥珀酰亚胺处理时，该化合物分解。因此，为了制备在甲基上官能化的衍生物，必须在硒代二唑环形成之前引入所需的取代基。通过这种方式，合成了相应的膦酸酯和一系列苯基醚。
• Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and 1,3-Dicarbonyl Compounds by using<i>N</i>-Bromosuccinimide as Oxidant
  作者：Wenbo Huang、Changhui Liu、Yanlong Gu

  DOI：10.1002/adsc.201700074

  日期：2017.6.6

  A simple aluminium(III) chloride‐catalyzed synthesis of tri‐substituted furans from aliphatic aldehydes and 1,3‐dicarbonyl compounds was developed by using N‐bromosuccinimide (NBS) as an oxidant. This method was effective for the synthesis of various furan derivatives. Some of the products were not accessible with the previously reported methods. Mechanically, this reaction involved an auto‐tandem

  使用N-溴代琥珀酰亚胺（NBS）作为氧化剂，开发了一种简单的氯化铝（III）催化的脂肪族醛和1,3-二羰基化合物合成三取代呋喃的方法。该方法对于合成各种呋喃衍生物是有效的。使用先前报告的方法无法访问某些产品。从机械上讲，该反应涉及一种基于新报道的酸-酸催化串联反应的自动串联催化，以确保呋喃得以成功合成。
• Reactions of Enaminones with Diazocarbonyl Compounds
  作者：Füsun Şeyma Güngör、Neslihan Hancıoğlu、Olcay Anaç

  DOI：10.1002/hlca.201200233

  日期：2013.3

  The [Cu(acac)2]‐catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino‐ and additionally carbonyl‐substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α‐carbonyl/α‐Ph groups, reactions proceeded only via 1,5‐electrocyclization of corresponding

  几种叔烯胺酮与三种重氮羰基化合物，即重氮丙二酸二甲酯，重氮乙酰乙酸乙酯，重氮乙酸乙酯的[Cu（acac）2 ]催化反应，可得到氨基和羰基取代的二氢呋喃，以及进一步的呋喃衍生物。由于α-羰基/ α- Ph基团的共轭作用，反应仅通过相应酮基的1,5-电环化进行。另一方面，在不存在任何α-取代基的情况下，叔烯胺酮和重氮乙酸乙酯通过 推挽式环丙烷中间体的一种伴随机理，可一步一步以中等收率产生2,4-二羰基取代的呋喃。
• Orientation in the Furan Nucleus. VII. Di-α-substituted Furans
  作者：Henry Gilman、N. O. Calloway、E. W. Smith

  DOI：10.1021/ja01316a069

  日期：1934.1
• Synthesis of ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and its reactions with nucleophiles
  作者：Yu. O. Remizov、L. M. Pevzner、M. L. Petrov、A. I. Ponyaev

  DOI：10.1134/s1070363215120117

  日期：2015.12

  By cyclization of carboethoxyhydrazone of ethyl 4-acetyl-5-methylfuran-2-carboxylate under the conditions of Hurd-Mori reaction ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate was synthesized. The ester obtained was brominated with N-bromosuccinimide at the methyl group in the furan ring. This bromide reacts with various N-, S-, O-, and P-nucleophiles to form the corresponding substitution products. Furylthiadiazole fragment remains stable in the course of these transformations.