Ethyl 5-phenylfuran-2-carboxylate | 60336-05-2

• 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 5-phenylfuran-2-carboxylate
• 英文别名: 2-(ethoxycarbonyl)-5-phenylfuran；5-phenyl-furan-2-carboxylic acid ethyl ester；Ethyl 5-phenyl-2-furoate
• CAS: 60336-05-2
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: UXKXEOYBIQKPTB-UHFFFAOYSA-N

物化性质

• 沸点：
  169-170 °C(Press: 1 Torr)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 5-phenylfuran-2-carboxylate 以41%的产率得到
  参考文献：
  名称：

  OLEJNIK A. F.; VOZYAKOVA T. I.; NOVITSKIJ K. YU.; ZYKOVA T. N.; GUSKOVA T+, XIM.-FARMATSEVT. ZH. , 1976, 10, HO 4, 46-49

  摘要：

  DOI：
• 作为产物：
  描述：

  5-苯基-2-糠酸 以39%的产率得到
  参考文献：
  名称：

  OLEJNIK A. F.; VOZYAKOVA T. I.; NOVITSKIJ K. YU.; ZYKOVA T. N.; GUSKOVA T+, XIM.-FARMATSEVT. ZH. , 1976, 10, HO 4, 46-49

  摘要：

  DOI：

文献信息

• One-step synthesis of 5-acylisothiazoles from furans
  作者：Jérôme Guillard、Christelle Lamazzi、Otto Meth-Cohn、Charles W. Rees、Andrew J. P. White、David J. Williams

  DOI：10.1039/b101157j

  日期：——

  Premixed ethyl carbamate, thionyl chloride and pyridine (which generate thiazyl chloride, NSCl) in boiling benzene or toluene convert 2,5- and 2,3,5-substituted furans into 5-acylisothiazoles regiospecifically. The reactions are much faster and generally higher yielding in boiling chlorobenzene with more thionyl chloride and with pyridine or isoquinoline as base. Under the more vigorous conditions, even fully substituted 3-bromofurans give isothiazoles, with the displacement of bromine. Deactivated furans, with electron-withdrawing groups such as ester, cyano, benzoyl and phenylsulfonyl in the α-position, react under the more vigorous conditions to give 5-acylisothiazoles with the electronegative group in the 3-position. The ‘activated’ 2-methyl-5-phenyl- and 5-phenyl-2-phenylthio-furans react analogously, with the more electron-releasing group becoming part of the 5-acyl substituent, exclusively or predominantly. These results are explained by initial electrophilic attack of the furan ring to give a β-thiazyl derivative which spontaneously ring-opens and closes to the isothiazole. The X-ray structures of five of the differently substituted isothiazole compounds are reported. All have very similar patterns of bonding within their isothiazole rings that appear to be independent of the electron-withdrawing or -donating nature of the substituents. Three of the compounds (8a, 8g and 13) have loosely linked chain structures in the solid state, adjacent molecules being connected by combinations of hydrogen bonding and π–π stacking interactions.

  预混的乙基氨基甲酸、亚硫酰氯和吡啶（生成噻唑氯，NSCl）在沸腾的苯或甲苯中能够进行区域特异性地将2,5-和2,3,5-取代的呋喃转化为5-酰基异噻唑。在沸腾的氯苯中，反应更快，产率普遍更高，且使用了更多的亚硫酰氯及吡啶或异喹啉作为碱。在更激烈的反应条件下，甚至完全取代的3-溴呋喃也能与溴发生取代反应生成异噻唑。对于那些带有电子吸引基团（如酯、氰、苯甲酰和苯磺酰）且位于α位的非活性呋喃，在较为激烈的条件下也能反应，生成5-酰基异噻唑，其中电负性基团位于3位。这些“活化”型的2-甲基-5-苯基和5-苯基-2-苯硫基呋喃也表现出类似的反应，其中电子供给基团会独占或主导成为5-酰基取代基。其结果可以通过呋喃环的初始亲电攻击解释，生成β-噻唑衍生物，随后自发环打开并闭合成异噻唑。报告了五种不同取代异噻唑化合物的X射线结构，所有化合物在其异噻唑环内的键合模式非常相似，似乎与取代基的电子吸引或供给特性无关。三种化合物（8a、8g和13）在固态下具有松散联接的链结构，邻近的分子通过氢键和π–π堆叠相互作用相连。
• Copper(I)-Catalyzed A³-Coupling Based Reaction of Alkynes, Aldehydes, and Amines: An Efficient Approach to 2,5-Polysubstituted Dihydrofurans and 2,5-Disubstituted Furans
  作者：Wu Fan、Shengming Ma

  DOI：10.1002/ejoc.201500209

  日期：2015.6

  An efficient and practical A3-coupling based reaction that gives a variety of 2,5-polysubstituted dihydrofurans and 2,5-disubstituted furan derivatives has been developed. This domino copper-catalyzed three-component coupling reaction of propargylic alcohol, ethyl glyoxalate, and an amine affords a propargylic amine intermediate, which undergoes an alkyne–allene isomerization followed by a cyclization

  已开发出一种有效且实用的基于 A3 偶联的反应，可生成多种 2,5-多取代二氢呋喃和 2,5-二取代呋喃衍生物。这种多米诺铜催化的炔丙醇、乙醛酸乙酯和胺的三组分偶联反应得到炔丙胺中间体，该中间体经过炔-丙二烯异构化，然后环化得到二氢呋喃。用 CH3I 和碱处理后，后者顺利转化为 2,5-二取代呋喃。或者，呋喃衍生物可以通过两步反应序列直接制备。
• 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。
• Mono- and Biscouplings Using Triarylbismuths for the Atom-Efficient Arylations of Functionalized Furans under Palladium Catalysis
  作者：Maddali Rao、Dheeraj Awasthi、Jalindar Talode

  DOI：10.1055/s-0032-1316567

  日期：2012.8

  Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one

  钯催化的功能化溴呋喃与三芳基铋的交叉偶联反应已被描述用于功能化芳基呋喃系统的原子经济合成。使用三芳基铋与各种 2-溴呋喃和 2,5-二溴呋喃的偶联反应顺利进行，在短反应时间（1 小时）内以高产率得到相应的 2-芳基呋喃和 2,5-二芳基呋喃。
• Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes
  作者：Alessandro Palmieri、Serena Gabrielli、Roberto Ballini

  DOI：10.1039/c0cc01097a

  日期：——

  The nitroaldol reaction of ketal-functionalized nitroalkanes with α-oxoaldehydes, promoted by Amberlyst A21, followed by acidic treatment (Amberlyst 15) of the obtained nitroalkanol, leads to the formation of 2,5-disubstituted furans in good yields. The procedure was successfully applied to the total synthesis of 1-benzyl-3-(5′-hydroxymethyl-2′-furyl)-indazole (YC-1), an important pharmaceutical target.

  在 Amberlyst A21 的促进下，酮官能化的硝基烷烃与 α-氧代醛发生硝基醛反应，然后对得到的硝基烷醇进行酸处理（Amberlyst 15），从而以良好的收率生成 2,5-二取代呋喃。该过程被成功应用于 1-苄基-3-（5′-羟甲基-2′-呋喃基）-吲唑（YC-1）的全合成，这是一种重要的药物目标物。