methyl 3-(furan-2-yl)-2,2-dimethyl-3-(phenylamino)propanoate | 79388-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-(furan-2-yl)-2,2-dimethyl-3-(phenylamino)propanoate
• 英文别名: methyl 3-(2-furyl)-2,2-dimethyl-3-(N-phenylamino)propionate；methyl 3-(2'-furyl)-2,2-dimethyl-3-(phenylamino)propionate；Methyl 3-anilino-3-(furan-2-yl)-2,2-dimethylpropanoate
• CAS: 79388-23-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: NGOMUHYJMGNWLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(furan-2-yl)-2,2-dimethyl-3-(phenylamino)propanoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以84%的产率得到4-(furan-2-yl)-3,3-dimethyl-1-phenylazetidin-2-one
  参考文献：
  名称：

  Convenient Synthesis of β-Lactams by the Reaction of Ketene Silyl Acetals with Schiff Bases Promoted by Titanium(IV) Chloride

  摘要：

  DOI：

  10.1055/s-1981-29520
• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (E)-1-(furan-2-yl)-N-phenylmethanimine 在 poly(etylene glycol) 、 ytterbium(III) triflate 作用下， 以 二氧化碳 为溶剂， 50.0 ℃ 、15.0 MPa 条件下， 反应 3.0h， 以75%的产率得到methyl 3-(furan-2-yl)-2,2-dimethyl-3-(phenylamino)propanoate
  参考文献：
  名称：

  Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes as Surfactant Molecules Which Enable Efficient Catalysis in ScCO₂

  摘要：

  Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO(2), poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO(2). In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO(2). Formation of emulsions was observed in these reactions, and the systems were studied in detail.

  DOI：

  10.1021/jo0353177

文献信息

• Brønsted Acid-Catalyzed Mannich-Type Reactions in Aqueous Media
  作者：Takahiko Akiyama、Jun Takaya、Hirotaka Kagoshima

  DOI：10.1002/1615-4169(200206)344:3/4<338::aid-adsc338>3.0.co;2-o

  日期：2002.6

  aldimines took place smoothly in aqueous organic solvent to afford β-aminocarbonyl compounds in high yields. The HBF4-catalyzed Mannich-type reaction also proceeded smoothly in water without organic solvent in the presence of a surfactant. A three-component synthesis starting from aldehyde, amine, and silyl enolate was successfully realized by means of a Bronsted acid in aqueous media.

  HBF4催化的甲硅烷基烯醇化物与醛亚胺的曼尼希型反应在水性有机溶剂中顺利进行，以高产率得到β-氨基羰基化合物。在表面活性剂存在下， 催化的曼尼希型反应在没有有机溶剂的水中也能顺利进行。借助布朗斯台德酸在水性介质中成功实现了从醛、胺和烯醇甲硅烷基开始的三组分合成。
• Solvent-free Imino-Aldol Three-component Couplings on a Conveniently-prepared and Reusable Phosphoric Acid-Silica Gel Support
  作者：Sandra Lock、Norikazu Miyoshi、Makoto Wada

  DOI：10.1246/cl.2004.1308

  日期：2004.10

  solvent-free procedure for the synthesis of β-amino carbonyl compounds in generally moderate to excellent yields has been developed. Three-component Mannich-type couplings between aldehydes (aromatic, aliphatic, alicyclic, and heterocyclic), aromatic amines and silyl enol equivalents proceeded smoothly on a conveniently prepared and reusable phosphoric acid-silica gel solid support.

  已经开发了一种新的无溶剂合成 β-氨基羰基化合物的方法，通常收率中等至极好。醛（芳香族、脂肪族、脂环族和杂环）、芳香族胺和甲硅烷基烯醇等价物之间的三组分曼尼希型偶联在方便制备且可重复使用的磷酸-硅胶固体载体上顺利进行。
• Polymer scandium-catalyzed three-component reactions leading to diverse amino ketone, amino ester, and amino nitrile derivatives
  作者：Shu Kobayashi、Satoshi Nagayama、Tsuyoshi Busujima

  DOI：10.1016/s0040-4039(96)02188-0

  日期：1996.12

  In the presence of a polymer-supported scandium catalyst (PA-Sc-TAD), three-component reactions between aldehydes, amines, and silylated nucleophiles proceeded smoothly to afford β-amino ketones, β-amino esters, and α-amino nitriles in high yields. These reactions provide a useful route to large numbers of structurally distinct amino group-containing compounds of high quality and quantity.

  在聚合物负载的caTAlyst催化剂（PA-Sc-TAD）的存在下，醛，胺和甲硅烷基化亲核试剂之间的三组分反应顺利进行，从而制得了β-氨基酮，β-氨基酯和α-氨基腈高产。这些反应提供了有用的途径，以得到大量高质量和大量的结构上不同的含氨基化合物。
• Mannich‐Type Reaction Catalyzed by Silica‐Supported Fluoroboric Acid under Solvent‐Free Conditions
  作者：WeiYi Chen、XinSheng Li、Jun Lu

  DOI：10.1080/00397910701796766

  日期：2008.1.1

  Abstract Three‐component Mannich‐type reaction of aldehydes, aromatic amines, and silyl enolate proceeded smoothly to afford β‐amino carbonyl compounds with good yields in the presence of a catalytic amount of HBF4‐SiO2.

  摘要 在催化量的 HBF4-SiO2 存在下，醛、芳香胺和甲硅烷基烯醇酯的三组分曼尼希型反应顺利进行，以良好的收率得到 β-氨基羰基化合物。
• Synthesis of Cage‐Shaped Borates Bearing Pyrenylmethyl Groups: Efficient Lewis Acid Catalyst for Photoactivated Glycosylations Driven by Intramolecular Excimer Formation
  作者：Yuya Tsutsui、Daiki Tanaka、Yoshiyuki Manabe、Yuka Ikinaga、Kumpei Yano、Koichi Fukase、Akihito Konishi、Makoto Yasuda

  DOI：10.1002/chem.202202284

  日期：2022.11.7

  groups was synthesized. The obtained 3aB functioned as a photoactivated Lewis acid catalyst. The photoactivation originates from the deformation of the cage-shaped scaffold driven by intramolecular excimer formations of the pyrenes, allowing the catalytic O-glycosylation using glycosyl fluorides to proceed with a high efficiency.

  合成了具有芘基甲基的笼形硼酸盐3a B 。得到的3a B 起光活化路易斯酸催化剂的作用。光活化源于由芘的分子内准分子形成驱动的笼形支架的变形，从而允许使用糖基氟化物的催化O-糖基化以高效率进行。