N-phenyl-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamyne

• 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-phenyl-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamyne
• 英文别名: phenyl(2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-yl)amine；N-phenyl-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-amine；N-phenyl-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine；(3aR,4S,9aS)-N-phenyl-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: QZYXOOXLRFQGSH-OIISXLGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 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：

  水杨醛 在 trityl tetrafluoroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-phenyl-N-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromen-4-ylamyne
  参考文献：
  名称：

  碳正离子有机催化作用于顺式稠合吡喃和呋喃苯并二氢吡喃的 Povarov 间断反应

  摘要：

  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%。

  DOI：

  10.1002/ejoc.201700634

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。
• Asymmetric Synthesis of cis-4-Aminobenzopyran Derivatives Catalyzed by N,N′-Dioxide-Sc(OTf)3 Complexes
  作者：Yulong Zhang、Shunxi Dong、Xiaohua Liu、Mingsheng Xie、Yin Zhu、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.201102058

  日期：2011.12.2

  The reactions of salicylaldimines with electron‐rich alkenes (2,3‐dihydro‐2H‐furan and 3,4‐dihydro‐2H‐pyran) catalyzed by N,N′‐dioxide–Sc(OTf)3 complexes were investigated. The methodology was successfully applied to the asymmetric synthesis of cis‐4‐aminobenzopyran derivatives. Excellent yields, diastereo‐ and enantioselectivities were observed for a broad range of substrates under mild conditions

  研究了水杨醛亚胺与富含电子的烯烃（2,3-二氢-2 H-呋喃和3,4-二氢-2 H-吡喃）在N，N'-二氧化物-Sc（OTf）3配合物催化下的反应。该方法已成功地用于不对称合成顺-4-氨基苯并吡喃衍生物。在温和条件下，对多种底物均观察到优异的收率，非对映和对映选择性（参见方案）。
• 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。
• 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。