Furfurylamine, N-(3,4-methylenedioxybenzylideno)-

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: Furfurylamine, N-(3,4-methylenedioxybenzylideno)-
• 英文别名: 1-(1,3-benzodioxol-5-yl)-N-(furan-2-ylmethyl)methanimine
• 化学式: C₁₃H₁₁NO₃
• mdl: MFCD00115504
• 分子量: 229.235
• InChiKey: ZRGUWQDVIMYVPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Furfurylamine, N-(3,4-methylenedioxybenzylideno)- 、 亚磷酸氢二甲酯 反应 24.0h， 生成 Dimethyl (benzo[d][1,3]dioxol-5-yl((furan-2-ylmethyl)amino)methyl)phosphonate
  参考文献：
  名称：

  α-Acylaminophosphonates possessing epoxyisoindolone moiety

  摘要：

  alpha-Acylaminophosphonates possessing an epoxyisoindolone moiety were prepared with good stereoselectivity (de >= 80%) by a tandem acylation/[4+2]-cycloaddition reaction between maleic anhydride and alpha-aminophosphonates derived from a furfurylamine. The cycloaddition products have an opposite orientation of epoxy and phosphonate groups, which was confirmed by NMR spectroscopy and X-ray crystal structure analysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.022
• 作为产物：
  描述：

  胡椒醛 、 2-呋喃甲胺 在 sodium sulfate 作用下， 以 甲苯 为溶剂， 生成 Furfurylamine, N-(3,4-methylenedioxybenzylideno)-
  参考文献：
  名称：

  α-Acylaminophosphonates possessing epoxyisoindolone moiety

  摘要：

  alpha-Acylaminophosphonates possessing an epoxyisoindolone moiety were prepared with good stereoselectivity (de >= 80%) by a tandem acylation/[4+2]-cycloaddition reaction between maleic anhydride and alpha-aminophosphonates derived from a furfurylamine. The cycloaddition products have an opposite orientation of epoxy and phosphonate groups, which was confirmed by NMR spectroscopy and X-ray crystal structure analysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.022

文献信息

• From Aryl Iodides to 1,3-Dipoles: Design and Mechanism of a Palladium Catalyzed Multicomponent Synthesis of Pyrroles
  作者：Gerardo M. Torres、Jeffrey S. Quesnel、Diane Bijou、Bruce A. Arndtsen

  DOI：10.1021/jacs.6b02314

  日期：2016.6.15

  palladium-catalyzed multicomponent synthetic route to polysubstituted pyrroles from aryl iodides, imines, carbon monoxide, and alkynes is described. To develop this reaction, a series of mechanistic studies on the [Pd(allyl)Cl]2/P(t)Bu3 catalyzed synthesis of imidazolinium carboxylates from aryl iodides, imines, and carbon monoxide were first performed, including model reactions for each individual step in the transformation

  描述了从芳基碘化物、亚胺、一氧化碳和炔烃制备多取代吡咯的钯催化多组分合成路线。为了开发该反应，首先对 [Pd(allyl)Cl]2/P(t)Bu3 催化从芳基碘化物、亚胺和一氧化碳合成咪唑啉羧酸盐进行了一系列机理研究，包括每个个体的模型反应转型的一步。这些表明该反应以并行串联催化方式进行，并涉及酰氯、N-酰基亚胺盐和最终1,3-偶极子（即Münchnones）的原位形成，用于随后的环加成。通过使用 Pd(P(t)Bu3)2/Bu4NCl 催化剂，该信息被用于设计 Münchnones 的第一个四组分合成。将后者与 1 耦合，与缺电子炔烃或烯烃的 3-偶极环加成可用于以良好的产率生成各种高度取代的吡咯族。这代表了一种模块化和简化的新方法，可以从容易获得的起始材料中获得此类杂环。
• A Nickel-Based, Tandem Catalytic Approach to Isoindolinones from Imines, Aryl Iodides, and CO
  作者：Jevgenijs Tjutrins、Jia Lun Shao、Veeranna Yempally、Ashfaq A. Bengali、Bruce A. Arndtsen

  DOI：10.1021/acs.organomet.5b00215

  日期：2015.5.26

  nickel-catalyzed synthesis of isoindolinones from imines, aryl iodides, and CO. This reaction is catalyzed by Ni(1,5-cyclooctadiene)2 in concert with chloride salts and postulated to proceed via a tandem nickel-catalyzed carbonylation to form N-acyl iminium chloride salts, followed by a spontaneous nickel-catalyzed cyclization. A range of aryl iodides and imines have been found to be viable substrates in

  我们在此描述了由亚胺，芳基碘化物和CO进行的模块化镍催化的异吲哚啉酮的合成。该反应由Ni（1,5-环辛二烯）2与氯化物盐协同催化，并假定通过串联的镍催化羰基化反应进行形成N-酰基亚胺基氯化铵盐，然后自发进行镍催化的环化反应。已发现一定范围的芳基碘化物和亚胺是该反应中可行的底物，提供了产生具有高原子经济性的取代的异吲哚啉酮的模块化途径。
• Palladium-Catalyzed, Multicomponent Approach to β-Lactams via Aryl Halide Carbonylation
  作者：Gerardo M. Torres、Maximiliano De La Higuera Macias、Jeffrey S. Quesnel、Oliver P. Williams、Veeranna Yempally、Ashfaq A. Bengali、Bruce A. Arndtsen

  DOI：10.1021/acs.joc.6b02405

  日期：2016.12.16

  A palladium-catalyzed multicomponent method for the synthesis of β-lactams from imines, aryl halides, and CO has been developed. This transformation proceeds via two tandem catalytic carbonylation reactions mediated by Pd(PtBu3)2 and provides a route to prepare these products from five separate reagents. A diverse range of polysubstituted β-lactams can be generated by systematic variation of the substrates

  已经开发了一种由亚胺，卤代芳基和一氧化碳合成β-内酰胺的钯催化多组分方法。该转化通过由Pd（P t Bu 3）2介导的两个串联催化羰基化反应进行，并提供了从五种单独的试剂制备这些产物的途径。通过底物的系统变化可以产生各种各样的多取代的β-内酰胺。该方法还可以扩展为使用碘取代的亚胺以高产率和选择性生产新型螺环β-内酰胺。
• α-Acylaminophosphonates possessing epoxyisoindolone moiety
  作者：Georgiy O. Kachkovskyi、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tet.2007.10.022

  日期：2007.12

  alpha-Acylaminophosphonates possessing an epoxyisoindolone moiety were prepared with good stereoselectivity (de >= 80%) by a tandem acylation/[4+2]-cycloaddition reaction between maleic anhydride and alpha-aminophosphonates derived from a furfurylamine. The cycloaddition products have an opposite orientation of epoxy and phosphonate groups, which was confirmed by NMR spectroscopy and X-ray crystal structure analysis. (c) 2007 Elsevier Ltd. All rights reserved.