1-[(dimethylamino)(3-nitrophenyl)methyl]-naphthalen-2-ol | 1346683-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(dimethylamino)(3-nitrophenyl)methyl]-naphthalen-2-ol
• 英文别名: 1-[dimethylamino-(3-nitrophenyl)methyl]naphthalen-2-ol
• CAS: 1346683-11-1
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: BZFMWRDHHRWDAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(dimethylamino)(3-nitrophenyl)methyl]-naphthalen-2-ol 在 溶剂黄146 作用下， 反应 6.0h， 以44%的产率得到14-(3-nitrophenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  The Mannich bases of naphthalene series in the synthesis of 14H-dibenzo[a,j]xanthenes

  摘要：

  DOI：

  10.1134/s1070363215040386
• 作为产物：
  描述：

  间硝基苯甲醛 、 二甲胺 、 2-萘酚 以 乙醇 、 水 为溶剂， 反应 50.0h， 以80%的产率得到1-[(dimethylamino)(3-nitrophenyl)methyl]-naphthalen-2-ol
  参考文献：
  名称：

  New synthesis of 3-amino-1H-benzo[f]chromene-2-carbonitriles

  摘要：

  3-Amino-1H-benzo[f]chromene-2-carbonitriles were synthesized by non-catalytic reaction from Mannich bases of the naphthalene series and malononitrile. Reactive 1-benzylidene(or methylidene)naphthalen-2(1H)-ones were presumed as intermediate products.

  DOI：

  10.1134/s1070428013030147

文献信息

• Reaction of Push–Pull Enaminoketones and <i>in Situ</i> Generated <i>ortho</i>-Quinone Methides: Synthesis of 3-Acyl-4<i>H</i>-chromenes and 2-Acyl-1<i>H</i>-benzo[<i>f</i>]chromenes as Precursors for Hydroxybenzylated Heterocycles
  作者：Anton V. Lukashenko、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.6b02716

  日期：2017.2.3

  developed. The chromenes are presumably formed through an initial oxa-Diels–Alder reaction, followed by an elimination of amine. The possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles, and pyridines has been demonstrated.

  已经开发了一种简单有效的方法，可以由邻醌甲基化物前体和推挽式烯酮合成吡喃环中含有三氟乙酰基或芳酰基的4 H-苯二甲基和1 H-苯并[ f ]苯二甲基。苯并二氢吡喃酮可能是通过最初的Oxa-Diels-Alder反应形成，然后消除胺而形成的。已经证明给定的色烯进一步转化为邻羟基苄基化的吡唑，异恶唑和吡啶的可能性。
• Reactions of naphthalen-2-ol Mannich bases with β-aminoacrylonitriles and methyl 3-morpholinoacrylate
  作者：Anton V. Lukashenko、Dmitry V. Osipov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02695-4

  日期：2020.5

  3-dihydro-1H-benzo[f]chromene-2-carbonitriles were obtained via the reaction of naphthalen-2-ol Mannich bases with β-aminoacrylonitriles and methyl 3-morpholinoacrylate as products of [4+2] cycloaddition of push-pull olefins to the corresponding 1,2-naphthoquinone 1-methide. The reaction of 3-amino-3-phenylacrylonitrile with Mannich bases leads to the formation of 1,4-dihydropyridine-3,5-dicarbonitriles.

  3-氨基-2,3-二氢-1 H-苯并[ f ]色烯和2-[（（2-羟基萘-1-基）甲基] -2,3-二氢-1 H-苯并[ f ]色烯-2通过萘-2-醇曼尼希碱与β-氨基丙烯腈和3-吗啉代丙烯酸甲酯的反应得到β-腈，β-氨基丙烯腈是推挽式烯烃[4 + 2]环加成到相应的1,2-萘醌1-甲基化物的产物。3-氨基-3-苯基丙烯腈与曼尼希碱的反应导致形成1,4-二氢吡啶-3,5-二碳腈。
• Synthesis of 2-Nitro-1H-Benzo[f]Chromenes
  作者：V. A. Osyanin、A. V. Lukashenko、D. V. Osipov、Yu. N. Klimochkin

  DOI：10.1007/s10593-014-1620-2

  日期：2015.2

  The reaction of Mannich bases derived from 2-naphthol with 4-(2-nitrovinyl)morpholine or N,N-di-methyl(2-nitrovinyl)amine in acetic anhydride gives 2-nitro-1H-benzo[f]chromenes. This reaction may be regarded formally as the addition of a push-pull olefin acting as a 1,2-ambiphile with naphthalenic o-quinone methide acting as a 1,4-ambiphilic reagent.

  衍生自2-萘酚的曼尼希碱与4-（2-硝基乙烯基）吗啉或N，N-二甲基（2-硝基乙烯基）胺在乙酸酐中的反应得到2-硝基-1H-苯并[f]二甲基苯。该反应在形式上可以被认为是添加了作为1，2-双亲分子的推挽式烯烃与作为1，4-双亲试剂的萘基邻醌甲基化物的加成。
• Complementary pairing of o-quinone methides with 3-(N,N-diethylamino)acrolein – synthesis of 1H-benzo[f]chromene-2-carbaldehydes
  作者：Anton V. Lukashenko、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1007/s10593-016-1941-4

  日期：2016.9

  A series of 1H-benzo[f]chromene-2-carbaldehydes was obtained from naphthol Mannich bases and 3-(N,N-diethylamino)acrolein via a cascade reaction comprising [4+2] cycloaddition of generated in situ 1,2-naphthoquinone-2-methides and a push-pull β-enaminoaldehyde with consecutive elimination of diethylamine.

  通过级联反应，从萘酚曼尼希碱和3-（N，N-二乙基氨基）丙烯醛中获得 一系列1 H-苯并[ f ]亚甲基-2-甲醛，该串联反应包括原位生成的1,2的环加成反应[4 + 2]。-萘醌-2-甲基化物和推挽式β-烯醛，并同时消除二乙胺。
• Reactions of <i>o</i>-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-<i>b</i>]furans and 2,3-Dihydrobenzofurans
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/jo400621r

  日期：2013.6.7

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.