6-chloro-N-phenyl-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine | 1360873-56-8

• 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: 6-chloro-N-phenyl-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
• 英文别名: (3aS,4R,9aR)-6-chloro-N-phenyl-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
• CAS: 1360873-56-8
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: OYMXUFUZRFRGPD-IAOVAPTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-氯代水杨醛 在 lithium tetrafluoroborate 、 sodium sulfate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 6-chloro-N-phenyl-3,3a,4,9a-tetrahydro-2H-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

• 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。
• 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%。