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

• 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-chlorophenyl)-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]-chromen-4-amine
• 英文别名: (3aR,4S,9aS)-N-(4-chlorophenyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: AXPDHBDNAGJZGY-OIISXLGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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 、 2-([(4-CHLOROPHENYL)IMINO]METHYL)PHENOL 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以81%的产率得到N-(4-chlorophenyl)-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]-chromen-4-amine
  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。
• Brønsted acids of anionic chiral Co(<scp>iii</scp>) complexes as catalysts for the stereoselective synthesis of cis-4-aminofuranobenzopyrans
  作者：Hua-Jie Jiang、Kun Liu、Jing Wang、Na Li、Jie Yu

  DOI：10.1039/c7ob02452e

  日期：——

  A highly enantioselective interrupted Povarov reaction of salicylaldimines and 2,3-dihydrofuran was developed, through the elegant Brønsted acid catalysis of anionic chiral Co(III) complexes. This reaction affords the cis-4-aminofuranobenzopyran derivatives with up to 95% yield, >20:1 dr and 96:4 er. Moreover, a one-pot three-component procedure of salicylaldehydes, anilines, and 2,3-dihydrofuran proves

  通过优雅的布朗斯台德酸催化阴离子手性Co（III）配合物，开发了水杨醛亚胺和2,3-二氢呋喃的高度对映选择性中断Povarov反应。该反应以高达95％的产率，> 20：1 dr和96：4 er提供了顺式-4-氨基呋喃并苯并吡喃衍生物。而且，水杨醛，苯胺和2，3-二氢呋喃的一锅三组分法被证明是成功的，具有更高的反应效率。
• 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%。
• 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
• LiBF4-catalyzed formation of fused pyrano- and furanobenzopyrans
  作者：J.S Yadav、B.V.Subba Reddy、Ch Madhuri、G Sabitha、B Jagannadh、S.Kiran Kumar、A.C Kunwar

  DOI：10.1016/s0040-4039(01)01257-6

  日期：2001.9

  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.