5-(N-allyl-N-methyl)amino-2-furancarboxaldehyde | 1017832-00-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(N-allyl-N-methyl)amino-2-furancarboxaldehyde
• 英文别名: N-methyl-N-allyl-5-amino-2-furaldehyde；5-[Methyl(prop-2-enyl)amino]furan-2-carbaldehyde；5-[methyl(prop-2-enyl)amino]furan-2-carbaldehyde
• CAS: 1017832-00-6
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: KGNLBBFCCYNPCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(N-allyl-N-methyl)amino-2-furancarboxaldehyde 、 六氟丙酮 以 甲苯 为溶剂， 反应 20.0h， 以57%的产率得到5-(N-allyl-N-methylamino)-4-(hexafluoro-2-hydroxypropan-2-yl)furan-2-carboxaldehyde
  参考文献：
  名称：

  三取代氨基呋喃和-噻吩衍生物的简便制备方法†

  摘要：

  β-烷基化 氨基呋喃-噻吩杂环通过无金属，无酸和无碱的碳-碳键形成来描述。通过实验和理论数据比较了两个杂环进行选择性β-烷基化的能力。手性胺取代基的存在诱导了新形成的另外的立体中心的非对映选择性的产生。

  DOI：

  10.1039/c1ob05216k
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 、 N-甲基烯丙基胺 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以78%的产率得到5-(N-allyl-N-methyl)amino-2-furancarboxaldehyde
  参考文献：
  名称：

  三取代氨基呋喃和-噻吩衍生物的简便制备方法†

  摘要：

  β-烷基化 氨基呋喃-噻吩杂环通过无金属，无酸和无碱的碳-碳键形成来描述。通过实验和理论数据比较了两个杂环进行选择性β-烷基化的能力。手性胺取代基的存在诱导了新形成的另外的立体中心的非对映选择性的产生。

  DOI：

  10.1039/c1ob05216k

文献信息

• Concise Synthesis of Tricyclic Isoindolinones via One-Pot Cascade Multicomponent Sequences
  作者：Raouf Medimagh、Sylvain Marque、Damien Prim、Jérôme Marrot、Saber Chatti

  DOI：10.1021/ol9003965

  日期：2009.4.16

  A series of enantiopure tricyclic isoindolinones has been successfully synthesized through a one-pot selective cascade process from furan derivatives. The synthesis is straightforward and gave good overall yields taking into account the concomitant formation of five C-C, C-O, and C-N bonds. The strategy was extended to the preparation of a thiazolidine analogue.
• From Furans to Anilines:  Toward One-Pot Two-Step Amination/Diels−Alder Sequences
  作者：Raouf Medimagh、Sylvain Marque、Damien Prim、Saber Chatti、Hédi Zarrouk

  DOI：10.1021/jo7024916

  日期：2008.3.1

  Selective metal-free amination and Diels-Alder reactions are described in the furan series, leading to polysubstituted anilines or to stable oxabicyclic adducts in high yield. Interestingly, anilines are conveniently prepared through a novel one-pot, two-step amination/Diels-Alder procedure from commercially available 5-bromo-2-furaldehyde.
• First Entry to [4+2] Cycloadditions Involving 5-Amino-2-furanmethanols
  作者：Sylvain Marque、Damien Prim、Raouf Medimagh、Saber Chatti

  DOI：10.3987/com-08-11556

  日期：——

  The preparation of new 5-amino-2-furanmethanols bearing various amino and primary or secondary alcohol groups is described. The structures of 5-amino-2-furanmethanols as dienes are consistent with (1)H NMR data and cyloadditions of them allows the selective synthesis of tetrasubstituted aminobenzylic alcohols, amino phenols or lactones through Diels-Alder reactions.
• 5-Amino-2-furylmethylamines - Appealing Precursors of Amino­isoindolinones?
  作者：Sylvain Marque、Raouf Medimagh、Damien Prim、Saber Chatti

  DOI：10.1055/s-0029-1218614

  日期：2010.3

  Isoindolinones were constructed according to an original [4+2]-cycloaddition strategy. Unprecedented 5-amino-2-furyl-methylamines were prepared and revealed as efficient precursors of new aminoisoindolinones, obtained via a Diels-Alder and lactamization sequence.
• A facile preparation of trisubstituted amino-furan and -thiophene derivatives
  作者：Raouf Medimagh、Sylvain Marque、Damien Prim、Saber Chatti

  DOI：10.1039/c1ob05216k

  日期：——

  β-Alkylation of amino-furan and -thiophene heterocycles is described through metal-, acid- and base-free carbon–carbon bond formation. The ability of both heterocycles to undergo selective β-alkylation is compared by mean of experimental and theoretical data. The presence of chiral amine substituents induced the diastereoselective generation of the newly formed additional stereocenter.

  β-烷基化 氨基呋喃-噻吩杂环通过无金属，无酸和无碱的碳-碳键形成来描述。通过实验和理论数据比较了两个杂环进行选择性β-烷基化的能力。手性胺取代基的存在诱导了新形成的另外的立体中心的非对映选择性的产生。