4-(furan-2-yl)butanenitrile | 90005-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-(furan-2-yl)butanenitrile
• 英文别名: 4-(2-furyl)butyronitrile；4-[2]furyl-butyronitrile；4-[2]Furyl-butyronitril；4-(Furan-2-yl)butanenitrile
• CAS: 90005-38-2
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: TZASWXZFWUNFTA-UHFFFAOYSA-N

物化性质

• 沸点：
  104-108 °C(Press: 10 Torr)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(furan-2-yl)butanenitrile 在 盐酸 、 氢氧化钾 、 sodium 、 苯酚 作用下， 生成 2-呋喃丁醇
  参考文献：
  名称：

  Hofmann et al., Journal of the American Chemical Society, 1949, vol. 71, p. 1253,1255

  摘要：

  DOI：
• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 在 Pd/SrCO₃ 、 乙醚 、 乙醇 、 三溴化磷 、 aluminum isopropoxide 、 异丙醇 、 苯 作用下， 生成 4-(furan-2-yl)butanenitrile
  参考文献：
  名称：

  125.ω-2'-呋喃烷烃衍生物

  摘要：

  DOI：

  10.1039/jr9530000618

文献信息

• Leveraging the Micellar Effect: Gold-Catalyzed Dehydrative Cyclizations in Water at Room Temperature
  作者：Stefan R. K. Minkler、Nicholas A. Isley、Daniel J. Lippincott、Norbert Krause、Bruce H. Lipshutz

  DOI：10.1021/ol403402h

  日期：2014.2.7

  The first examples of gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles in an aqueous medium are presented. These reactions take place within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. By the addition of simple salts such as sodium chloride, reaction times and catalyst loadings

  介绍了在水介质中金催化的二醇和三醇环化成相应杂环或螺环的第一个例子。这些反应发生在纳米胶束内，疏水作用在其中起作用，从而推动脱水，尽管周围有水。通过添加简单的盐，例如氯化钠，可以显着减少反应时间和催化剂负载。
• Conformational preferences of oxy-substituents in butenolide–tetrahydropyran spiroacetals and butenolide–piperidine spiro-N,O-acetals
  作者：Sébastien Naud、Sarah J. Macnaughton、Bryony S. Dyson、Daniel J. Woollaston、Jonathan W. P. Dallimore、Jeremy Robertson

  DOI：10.1039/c2ob06849d

  日期：——

  of a series of oxy-substituted butenolide spiroacetals and spiro-N,O-acetals by oxidative spirocyclisation of 2-[(4-hydroxy or 4-sulfonamido)butyl]furans. The axial–equatorial preference of each oxy-substituent is investigated (NMR) by an acid-catalysed thermodynamic relay of configuration between the spiro- and oxy-centres. The axial site is preferred for most oxy-substituents at synthetically useful

  我们描述了2-[（4-羟基或4-磺酰胺基）丁基]呋喃的氧化螺环化反应，合成了一系列氧取代的丁烯内酯螺缩醛和螺-N，O-缩醛。通过在螺中心和氧中心之间构型的酸催化热力学继电器研究了每个氧取代基的轴向-赤道偏爱度（NMR）。对于大多数含氧取代基，在合成上有用的水平，轴向位点是优选的。根据稳定的纱布效应和溶剂化的影响讨论了这种偏爱的潜在来源。这些结果与包括AL-1和相关化合物的双（炔）烯醇醚螺缩醛的合成有关。
• Synthesis of DNA Conjugates with Metalated Tetracationic Porphyrins by Postsynthetic Cycloadditions
  作者：Christian Wellner、Hans-Achim Wagenknecht

  DOI：10.1021/ol500364j

  日期：2014.3.21

  Tetracationic porphyrins of the TMPP (meso-tetra-(4-N-methylpyridyl)porphyrin) type, metalated with Cu(II) or with Au(III), were conjugated covalently to oligonucleotides. The Cu(I)-catalyzed cycloaddition (between an azide and an ethynyl group) and the Diels-Alder cycloaddition (between a furan and a maleimide functionality) were successfully applied as two alternative postsynthetic methods to modify the 2'-position of an internal uridine. Melting temperatures and UV/vis absorption properties were compared. CD measurements indicated that the type of conjugation chemistry determines the grade of intercalation of the attached and positively charged porphyrins.
• Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems
  作者：Albert Padwa、Donald L. Hertzog、William R. Nadler

  DOI：10.1021/jo00102a037

  日期：1994.11

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.
• 555. Some experiments with furans
  作者：D. A. H. Taylor

  DOI：10.1039/jr9590002767

  日期：——