4-[5-(3-oxobutyl)-2-furyl]-2-butanone | 78466-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-[5-(3-oxobutyl)-2-furyl]-2-butanone
• 英文别名: 2,5-bis(3'-oxobutyl)furan；2,5-di(3-oxobutyl)-furan；4-[5-(3-Oxobutyl)furan-2-yl]butan-2-one
• CAS: 78466-07-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: LKKXDKMQABACNH-UHFFFAOYSA-N

物化性质

• 沸点：
  174-176 °C(Press: 12 Torr)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[5-(3-oxobutyl)-2-furyl]-2-butanone 在 甲醇 、 氨 、 镍 作用下， 75.0~90.0 ℃ 、29.42 MPa 条件下， 生成 2,5-Bis-(3-amino-butyl)-furan
  参考文献：
  名称：

  Addition of Heterocycles to Conjugate Unsaturated Carbonyl Compounds: Difunctional Derivatives

  摘要：

  DOI：

  10.1021/ja01146a074
• 作为产物：
  描述：

  4-[5-(3-oxobut-1-enyl)furan-2-yl]but-3-en-2-one 在 甲醇 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到4-[5-(3-oxobutyl)-2-furyl]-2-butanone
  参考文献：
  名称：

  Chemoselective reduction in carbonyl-conjugated vinylfurans by the Mg/MeOH system

  摘要：

  Chemoselective reduction of double bonds conjugated with carbonyl groups and furan rings has been acomplished by using Mg/MeOh reducing system.

  DOI：

  10.1016/s0040-4039(00)79899-6

文献信息

• Addition of heterocycles to electron deficient olefins and alkynes catalyzed by gold(III)
  作者：Zigang Li、Zhangjie Shi、Chuan He

  DOI：10.1016/j.jorganchem.2005.03.009

  日期：2005.11

  A gold(III)-catalyzed hydroarylation of different olefins is reported here. AuCl3 works as an excellent catalyst to mediate reactions between various heterocycles and electron deficient olefins and alkynes under mild conditions. This gold(III)-based method tolerates different functional groups such as aldehyde, carboxylic acid, nitrile, and is highly efficient. We have shown that some of these reactions

  此处报道了金（III）催化的不同烯烃的加氢芳基化反应。AuCl 3是出色的催化剂，可在温和条件下介导各种杂环与缺电子的烯烃和炔烃之间的反应。这种基于金（III）的方法可以耐受不同的官能团，例如醛，羧酸，腈，并且效率很高。我们已经表明，其中一些反应在室温下可在数分钟内完成。
• Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; conformationally-controlled oligomers bearing electroactive groups
  作者：Roger W. Alder、Niall P. Hyland、John C. Jeffery、Thomas Riis-Johannessen、D. Jason Riley

  DOI：10.1039/b901060b

  日期：——

  The design of polymers with repeating [C(NR2)2CH2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed.

  讨论了设计含有重复[C(NR2)2CH2CH2]单元的聚合物的设计，这些单元可以同时提供构象控制和含有重复的电活性中心；（NR2)2基团将理想地由邻苯二胺衍生物提供，以1,8-二氨基萘作为替代品。通过CH3[COCH2CH2]nCOCH3与1,8-双(甲基氨基)萘的缩聚反应，得到了含有1,8-双(甲基氨基)萘的低聚物，最多达到六聚体，但试图从1,2-双(烷基氨基)苯制备相关低聚物的尝试未能成功，因为只有末端酮基团可以转化为缩二氨酸。通过环流对1H NMR位移的影响以及X射线结构，提供了对萘二胺低聚物主链中所有反式构象有强烈倾向的证据，这些结构还提供了在固态下的插层证据。对这些低聚物的电化学研究表明，溶液中的低聚物氧化是不可逆的，但对较长低聚物的氧化会导致沉积出呈现两个可逆氧化波的红色不溶物质。对这些结果的可能解释进行了讨论。
• Approaches to Open Fullerenes:  Synthesis and Kinetic Stability of Diels−Alder Adducts of Substituted Isobenzofurans and C₆₀
  作者：Shih-Ching Chuang、Michael Sander、Thibaut Jarrosson、Scott James、Eugene Rozumov、Saeed I. Khan、Yves Rubin

  DOI：10.1021/jo061986j

  日期：2007.4.1

  examined the reactions of 1,3-disubstituted isobenzofurans with the fullerene C60 in the context of an approach to open a large orifice on the fullerene framework. A variety of substituted isobenzofurans (6a−h), generated from the reaction of 1,4-substituted 1,4-epoxynaphthalenes 3a−h with 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine (4a) or 1,2,4,5-tetrazine (4b), were added to C60 to afford the Diels−Alder adducts

  我们已经研究了在富勒烯骨架上开大孔的方法中1，3-二取代异苯并呋喃与富勒烯C 60的反应。1,4-取代的1,4-环氧萘3a - h与3,6-双（2-吡啶基）-1,2,4,5-四嗪反应生成的各种取代的异苯并呋喃（6a - h）将（4a）或1,2,4,5-四嗪（4b）添加到C 60中以提供Diels-Alder加合物7a - h。这些加合物对逆Diels-Alder碎裂的热稳定性在溶液中与固态有很大不同。在溶液中，单加成物的相对容易的逆狄尔斯-阿尔德碎裂7A和图7C，得到C，60和自由isobenzofurans 6A和6C，具有速率常数（和活化障碍）ķ = 9.29×10 - 5个小号- 1在70℃（Ë一个= 32.6千卡摩尔- 1）和ķ = 1.36×10 - 4个小号- 1在40℃下（Ëa = 33.7 kcal mol - 1），表明在这些温度下向C 60中添加异苯并呋喃很容易可逆。在
• Magnesium monoperoxyphtalate: A new reagent for the oxidative ring opening of furans to cis-enediones
  作者：Carmen Dominguez、Aurelio G. Csa´ky、Joaquin Plumet'

  DOI：10.1016/s0040-4039(00)97328-3

  日期：1990.1

  Ring opening of furans can be accomplished with the title reagent to afford cis-enediones stereospecifically, with great advantages over the hazardous MCPBA.

  呋喃的开环可以用标题试剂完成，从而立体定向地提供顺式-二烯二酮，与危险的MCPBA相比具有很大的优势。
• Halogen Bond‐Catalyzed Friedel−Crafts Reactions of Furans Using a 2,2’‐Bipyridine‐Based Catalyst
  作者：Huimiao Zhang、Patrick H. Toy

  DOI：10.1002/adsc.202001019

  日期：2021.1.5

  to catalyze Friedel−Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so

  基于2，2'-联吡啶骨架的卤素键供体已经合成，并用于催化呋喃的Friedel-Crafts反应。在这些反应中成功使用的亲电试剂包括各种烯酮，醛和羧酸酐。在相对较低的温度（室温或50℃）下，在乙腈中使用适度的催化剂负载量（0.025或0.1当量），反应的收率通常很高。使用的催化剂设计有联芳基支架，因此，如果确实证明它是有效的卤素键供体有机催化剂，则其对映体富集的形式可能会用作立体选择性催化剂。