3-(furan-2-yl)propiolaldehyde

• 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: 3-(furan-2-yl)propiolaldehyde
• 英文别名: 3-(Furan-2-yl)prop-2-ynal；3-(furan-2-yl)prop-2-ynal
• 化学式: C₇H₄O₂
• 分子量: 120.108
• InChiKey: QWIHVZNZZVESDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)propiolaldehyde 在 Ag⁽¹⁺⁾*2CO₃^(2-) 、 DL-脯氨酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 1.0h， 生成 2-(furan-2-ylmethylene)-3-(2-oxopropyl)-2H-furo[3,2-c]chromen-4(3H)-one
  参考文献：
  名称：

  Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins

  摘要：

  A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

  DOI：

  10.1021/ol502551u
• 作为产物：
  描述：

  糠醛 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 3-(furan-2-yl)propiolaldehyde
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287

文献信息

• “One-Pot” Access to 4<i>H</i>-Chromenes with Formation of a Chiral Quaternary Stereogenic Center by a Highly Enantioselective Iminium-allenamine Involved Oxa-Michael−Aldol Cascade
  作者：Chunliang Liu、Xinshuai Zhang、Rui Wang、Wei Wang

  DOI：10.1021/ol102096s

  日期：2010.11.5

  organocatalytic highly enantioselective cascade Michael−aldol reaction has been developed in high yields under mild reaction conditions. The “one-pot” process affords an efficient approach to the synthetically and biologically important chiral 4H-chromenes bearing a quaternary stereogenic center. The study significantly expands the scope of less explored organocatalytic iminium-allenamine chemistry.

  在温和的反应条件下，高收率地开发了前所未有的有机催化高对映选择性级联迈克尔-醛醇缩合反应。“一锅法”工艺为合成和生物学上重要的手性4 H-色烯带有一个四级立体异构中心提供了一种有效的方法。该研究极大地扩展了较少探索的有机催化亚胺-亚胺胺化学的范围。
• N-Heterocyclic carbene-catalyzed annulation of ynals with amidines: access to 1,2,6-trisubstituted pyrimidin-4-ones
  作者：Yangxi Xie、Jian Wang

  DOI：10.1039/c8cc02023j

  日期：——

  A thiazolium-catalyzed annulation of ynals and amidines has been reported to construct pyrimidin-4-ones.

  一种噻唑嗪催化的ynals和胺亚胺的环化反应已被报道用于构建嘧啶-4-酮。
• Enantioselective Organocatalyzed Oxa-Michael-Aldol Cascade Reactions: Construction of Chiral 4<i>H</i>-Chromenes with a Trifluoromethylated Tetrasubstituted Carbon Stereocenter
  作者：Jing Zhang、Manjaly J. Ajitha、Lin He、Kai Liu、Bin Dai、Kuo-Wei Huang

  DOI：10.1002/adsc.201400977

  日期：2015.3.23

  tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa‐Michael–aldol cascade reaction between alkynals and 2‐trifluoroacetylphenols via iminium–allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled‐up easily with maintenance of the excellent enantioselectivity.

  提出了带有三氟甲基化四取代碳中心的4 H-色烯的第一个有机催化不对称合成。手性仲胺通过亚胺基-亚胺基的活化作用促进炔烃和2-三氟乙酰基苯酚之间的氧杂-迈克尔-奥尔多级联反应，从而产生具有重要对映选择性的重要药学上重要的杂环。拟议的反应可以轻松扩大规模，同时保持出色的对映选择性。
• Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles
  作者：Daniel Hack、Pankaj Chauhan、Kristina Deckers、Yusuke Mizutani、Gerhard Raabe、Dieter Enders

  DOI：10.1039/c4cc09495f

  日期：——

  A one-pot sequential bicatalytic asymmetric Michael addition/hydroalkoxylation provides a new series of pyrano-annulated enantioenriched pyrazole derivatives.

  一锅串联的双酶催化不对称Michael加成/水解烷基化反应提供了一系列新的缩合环化手性富集的吡唑衍生物。
• Cooperative N-heterocyclic carbene (NHC)–Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins
  作者：Yu Zhang、Yingyan Lu、Weifang Tang、Tao Lu、Ding Du

  DOI：10.1039/c4ob00145a

  日期：——

  A novel and regioselective umpolung synthesis of spirooxindoles has been developed by cooperative NHC–Lewis acid-mediated formal [3 + 2] annulations of alkynyl aldehydes with isatins. In most cases, the reactions proceeded via a3–d3 umpolung of alkynyl aldehydes resulting in spirooxindole butenolides. In a few cases, spirooxindole furan-3(2H)-ones were formed as the major products via an a1–d1 umpolung

  通过NHC-刘易斯酸介导的炔醛与靛红的正式[3 + 2]环合反应，开发了一种新颖的区域选择性螺环螺螺合成方法。在大多数情况下，反应进行经由一个3 -d 3导致spirooxindole丁烯羟酸内酯炔醛的极性转换。在少数情况下，spirooxindole呋喃-3-（2 ħ） -酮形成作为主要产物通过一个一个1 -d 1通过控制反应温度极性转换过程。这些新形成的螺菌毒素可以为化学生物学和药物铅发现提供有希望的候选者。