ethyl 2-formylfuran-3-carboxylate | 19076-56-3

• 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 2-formylfuran-3-carboxylate
• 英文别名: ethyl 2-formyl-3-furoate；2-formyl-furan-3-carboxylic acid ethyl ester；2-Formyl-3-carbethoxy-furan
• CAS: 19076-56-3
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: MOBPCMQBARMUHY-UHFFFAOYSA-N

物化性质

• 熔点：
  46 °C
• 沸点：
  280.4±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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 2-formylfuran-3-carboxylate 在 正丁基锂 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 生成 ethyl (2E,4E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]furan-3-yl]penta-2,4-dienoate
  参考文献：
  名称：

  Stereoselective synthesis and receptor activity of conformationally defined retinoid X receptor selective ligands

  摘要：

  Retinoid X Receptor (RXR) specific ligands are currently being investigated for the treatment of metabolic diseases such as type II diabetes. We report the synthesis of conformationally locked retinoids, which are potent RXR selective ligands, and the attempted synthesis of 9-cyclopropyl locked analogs of RA and 9-cis RA. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00048-7
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 生成 ethyl 2-formylfuran-3-carboxylate
  参考文献：
  名称：

  Synthesis of 2,3-dicarbonylated pyrroles and furans via the three-component Hantzsch reaction

  摘要：

  Pyrroles containing a 2,3-dicarbonyl substitution pattern are synthesized in one step via a three-component Hantzsch procedure. The normally difficult-to-access substrates are readily obtained in short reaction times and in moderate to good yields, giving pharmaceutically attractive products containing multiple handles for further elaboration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.022

文献信息

• Two practical syntheses of an anti-inflammatory sesquiterpene furoic acid from Sinularia spp
  作者：David H. Williams、D. John Faulkner

  DOI：10.1016/0040-4020(96)00133-0

  日期：1996.3

  The sesquiterpene (1′E,5′E)-2-(2′,6′-dimethylocta-1′,5′,7′-trienyl)-4-furoic acid (2), which is an anti-inflammatory metabolite of the soft coral Sinularia spp. has been synthesized by two routes, both of which employ a Claisen rearrangement.

  倍半萜烯（1' é，5' ë）-2-（2'，6'-二甲1'，5'，7'-三烯基）-4-糠酸（2），这是一种抗炎代谢物的软珊瑚Sinularia spp。由两条路线合成，两条路线均采用克莱森重排。
• Intra-molecular Diels–Alder reactions of citraconamic acids from furfurylamines and citraconic anhydride: effects of substitution in the furan ring on regioselectivity
  作者：Rajappa Murali、H Surya Prakash Rao、Hans W Scheeren

  DOI：10.1016/s0040-4020(01)00175-2

  日期：2001.4

  Regioselectivity in the intra-molecular Diels–Alder (IMDA) reaction of furfurylcitraconamic acids derived from N-benzylfurfurylamines and citraconic anhydride can be controlled by substituents located in the furan ring and by reaction conditions. Reactions conducted under kinetic conditions resulted in cycloaddition products having methyl and aminomethylene substituent in 1,3-relationship whereas under

  由呋喃环中的取代基和反应条件可以控制N-苄基糠胺和柠康酸酐衍生的糠基柠檬烯二酸酯分子内Diels-Alder（IMDA）反应中的区域选择性。在动力学条件下进行的反应导致在1,3-关系中具有甲基和氨基亚甲基取代基的环加成产物，而在热力学条件下，除3-甲基硫烷基外，该产物重排成更稳定的环加合物，其中取代基位于1 ，2-关系。可以根据边界轨道相互作用和空间考虑因素来解释产物的形成。
• Isoindolone Formation via Intramolecular Diels–Alder Reaction
  作者：Matthew Ball、Alistair Boyd、Gwydion Churchill、Murray Cuthbert、Mark Drew、Mark Fielding、Gair Ford、Lianne Frodsham、Michael Golden、Kevin Leslie、Sarah Lyons、Ben McKeever-Abbas、Andrew Stark、Paula Tomlin、Stephen Gottschling、Abraham Hajar、Ji-long Jiang、Josephine Lo、Bob Suchozak

  DOI：10.1021/op300002f

  日期：2012.5.18

  The intramolecular Diels–Alder reaction provides a useful synthetic methodology to build biologically active and synthetically useful isoindolone ring systems. An application of this methodology, providing an efficient manufacturing route to an mGluR2 positive allosteric modulator via a 1,5,7-substituted isoindolone, is reported herein.

  分子内的狄尔斯-阿尔德反应提供了一种有用的合成方法，可以建立具有生物活性和合成意义的异吲哚酮环系统。本文报道了该方法的应用，其通过1,5,7-取代的异吲哚酮提供了向mGluR2阳性变构调节剂的有效制造途径。
• Gabaergic Agents to Treat Memory Deficits
  申请人：Cook James M.

  公开号：US20100130479A1

  公开（公告）日：2010-05-27

  The present invention provides molecules and methods for the prevention and/or treatment of memory deficit related conditions and/or enhancement of cognition. In a preferred embodiment, the invention includes compounds, salts and prodrugs thereof for the prevention and/or treatment of these conditions.

  本发明提供了预防和/或治疗与记忆缺陷相关疾病和/或增强认知的分子和方法。在一个优选实施例中，本发明包括化合物、盐及其前药，用于预防和/或治疗这些疾病。
• Process for producing catalyst ingredient for use in olefin polymerization
  申请人：Tonen Corporation

  公开号：EP0227455A2

  公开（公告）日：1987-07-01

  A process for producing catalyst ingredient for use in olefin polymerisation which comprises (A) contacting a magnesium hydrocarbyloxide and a silicon compound having hydrogen-silicon bonds in the presence of a hydrocarbon medium. contacting the thus obtained solid product with (B) a halogenated titanium compound in the presence or absence of a hydrocarbon medium and then adding to the contact product (C) an electron donating compound.

  一种用于烯烃聚合的催化剂成分的生产工艺，包括(A)在有烃介质存在的情况下，将氢氧化镁和具有氢硅键的硅化合物接触；(B)在有或无烃介质存在的情况下，将由此得到的固体产品与卤化钛化合物接触，然后向接触产品中加入(C)电子捐赠化合物。