N-(4-methylphenyl)-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(4-methylphenyl)-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamine
• 英文别名: (4-methylphenyl)2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamine；N-(p-tolyl)-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-amine；(3aR,4S,9aS)-N-(4-methylphenyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: JVXPYIBALBHLRS-NXHRZFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 Phenol, 2-[[(4-methylphenyl)imino]methyl]-, (Z)- 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以90%的产率得到N-(4-methylphenyl)-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamine
  参考文献：
  名称：

  LiBF4-catalyzed formation of fused pyrano- and furanobenzopyrans

  摘要：

  Lithium tetrafluoroborate efficiently catalyzes an unusual cyclization of o-hydroxybenzaldimines with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran at ambient temperature to afford a class of new pyrano- and furanobenzopyran derivatives in excellent yields with high diastereo selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01257-6

文献信息

• Catalytic Asymmetric Inverse-Electron-Demand (IED) [4+2] Cycloaddition of Salicylaldimines: Preparation of Optically Active 4-Aminobenzopyran Derivatives
  作者：Luca Bernardi、Mauro Comes-Franchini、Mariafrancesca Fochi、Virginia Leo、Andrea Mazzanti、Alfredo Ricci

  DOI：10.1002/adsc.201000608

  日期：2010.12.17

  The catalytic asymmetric inverse-electron-demand (IED) [4+2] cycloaddition of various salicylaldehyde-derived N-arylimines with electron-rich alkenes in the presence of chiral BINOL-derived phosphoric acid catalysts has been studied with the aim of obtaining optically active 4-aminobenzopyran derivatives. Dienophiles such as 2,3-dihydro-2H-furan, benzyl N-vinylcarbamate and 2-vinylindole have been

  研究了手性BINOL衍生的磷酸催化剂存在下，各种水杨醛衍生的N-芳基胺与富电子烯烃的催化不对称逆电子需求（IED）[4 + 2]环加成反应，目的是通过光学手段获得活性4-氨基苯并吡喃衍生物。亲二烯体如2,3-二氢-2 ħ -呋喃，苄基Ñ -vinylcarbamate和2-哚已经采用。
• Carbocation Organocatalysis in Interrupted Povarov Reactions to <i>cis</i> -Fused Pyrano- and Furanobenzodihydropyrans
  作者：Jingjing Liu、Jiaxi Xu、Zhenjiang Li、Yu Huang、Haixin Wang、Yu Gao、Tianfo Guo、Pingkai Ouyang、Kai Guo

  DOI：10.1002/ejoc.201700634

  日期：2017.7.25

  Tritylium cation catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90%) within 10 min by low catalyst loading (1 mol %). Lewis acidic catalysis mechanism by carbocation was proposed and validated. Switching a one-pot batch version of the reaction into a two-stage convergent continuous flow procedures received 10-fold time reduction to 1 min with 88%

  三苯甲基阳离子催化的间断 Povarov 反应在 10 分钟内通过低催化剂负载 (1 mol%) 以优异的产率 (90%) 提供顺式 4-氨基苯并二氢吡喃。提出并验证了碳正离子的路易斯酸性催化机理。将反应的一锅批量版本转换为两阶段会聚连续流程序，时间减少了 10 倍，达到 1 分钟，产率为 88%。
• Inverse Electron Demand Diels-Alder Reactions of Heterodienes Catalyzed by Potassium Hydrogen Sulfate: Diastereoselective, One-Pot Synthesis of Pyranobenzopyrans, Furanobenzopyrans and Tetrahydroquinolines Derivatives
  作者：Paramasivan T. Perumal、R. Senthil Kumar、Rajagopal Nagarajan

  DOI：10.1055/s-2004-822332

  日期：——

  Potassium hydrogen sulfate catalyzes the one-pot three components coupling of aldehydes, anilines, and electron rich dienophiles such as dihydropyran, dihydrofuran, ethyl vinylether, and cyclopentadiene. With o-hydroxybenzaldehyde, the reaction probably proceeds through the formation of o-quinonemethide intermediate, which subsequently undergoes cycloaddition with cyclic and acyclic enol ethers leading

  硫酸氢钾催化醛、苯胺和富电子双烯体如二氢吡喃、二氢呋喃、乙基乙烯基醚和环戊二烯的一锅三组分偶联。对于邻羟基苯甲醛，反应可能通过形成邻醌甲基化物中间体进行，该中间体随后与环状和非环状烯醇醚进行环加成反应，形成相应的色烷。然而，在没有邻羟基的苯甲醛的情况下，形成的亚胺充当杂二烯并导致形成四氢喹啉。
• Bi(OTf)₃-[Bmim]PF₆: A novel and Recyclable Catalytic System for the Diasteroselective Synthesis of Cis-fused Pyrano and Furanobenzopyrans
  作者：J. S. Yadav、B. V. S. Reddy、P. Narayana Reddy

  DOI：10.1246/cl.2004.1436

  日期：2004.11

  The Stereoselective one-pot synthesis of cis-fused pyrano and furanobenzopyrans has been developed from o-hydroxybenzaldehydes, aromatic amines, and cyclic enol ethers in the presence of Bi(OTf) 3 in air- and moisture-stable ionic liquid, [bmim]PF 6 under mild conditions. The recovered ionic liquid containing Bi(OTf) 3 can be reused three to five subsequent runs with only a gradual decrease in activity

  在空气和水分稳定的离子液体 [bmim] 中，在 Bi(OTf) 3 存在下，从邻羟基苯甲醛、芳香胺和环烯醇醚开发了顺式稠合吡喃和呋喃苯并吡喃的立体选择性一锅法合成PF 6 在温和条件下。回收的含有 Bi(OTf) 3 的离子液体可以重复使用三到五次，而活性只会逐渐降低。[bmim]PF 6 的疏水性质促进了催化剂的回收。
• NaHSO₄–SiO₂-catalyzed aza-Diels–Alder reaction of <i>o</i>-hydroxybenzaldimines with 2,3-dihydrofuran: Diastereoselective synthesis of furanobenzopyrans
  作者：Pfanelo Mulokwe、Mokgethwa B. Marakalala、Tommy F. Mabasa、Henok H. Kinfe

  DOI：10.1080/00397911.2017.1377257

  日期：2017.12.17

  ABSTRACT NaHSO4 supported on silica gel catalyzes the aza-Diels–Alder reaction of o-hydroxybenzaldimines with 2,3-dihydrofuran to provide furanobenzopyrans in reasonable yields and diastereoselectivity. The catalyst is recyclable and reusable up to two times without a significant loss of activity. GRAPHICAL ABSTRACT

  摘要 硅胶负载的 NaHSO4 催化邻羟基苯甲醛二亚胺与 2,3-二氢呋喃的 aza-Diels-Alder 反应，以合理的产率和非对映选择性提供呋喃苯并吡喃。该催化剂可循环使用，最多可重复使用两次，而不会显着降低活性。图形概要