1-(dimethylamino-(thiophen-2-yl)-methyl)naphthalen-2-ol | 1346683-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(dimethylamino-(thiophen-2-yl)-methyl)naphthalen-2-ol
• 英文别名: 1-[(Dimethylamino)(2-thienyl)methyl]-2-naphthol；1-[dimethylamino(thiophen-2-yl)methyl]naphthalen-2-ol
• CAS: 1346683-12-2
• 化学式: C₁₇H₁₇NOS
• 分子量: 283.394
• InChiKey: IJAAXLHGCSQONN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(dimethylamino-(thiophen-2-yl)-methyl)naphthalen-2-ol 在 溶剂黄146 作用下， 反应 6.0h， 以45%的产率得到14-(2-thienyl)-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：

  2-噻吩甲醛 、 二甲胺 、 2-萘酚 以 乙醇 为溶剂， 反应 120.33h， 以40%的产率得到1-(dimethylamino-(thiophen-2-yl)-methyl)naphthalen-2-ol
  参考文献：
  名称：

  衍生自2-萘酚，芳香醛和仲脂肪胺的曼尼希碱的抗菌活性

  摘要：

  通过2-萘酚与（杂）芳族醛和仲胺的直接Mannich反应合成了一个小的1-氨基烷基2-萘酚文库。所有结构中具有噻吩-2-基环的曼尼希碱基均对革兰氏阳性细菌具有良好的活性，而与氨基部分的性质无关。

  DOI：

  10.1016/j.bmcl.2016.03.098

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。
• An Inverse Electron Demand Azo-Diels–Alder Reaction of <i>o</i>-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines
  作者：Dmitry V. Osipov、Vitaly A. Osyanin、Guzel’ D. Khaysanova、Elvira R. Masterova、Pavel E. Krasnikov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.8b00692

  日期：2018.4.20

  the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels–Alder reaction, and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.

  我们已经研究了邻醌甲基化物前体与亚氨基醚的反应。该反应提供了取代的1，3-苯并恶嗪的通用途径。拟议的反应机制涉及邻醌甲基化物中间体的产生，亚氨基-狄尔斯-阿尔德反应和消除。这种级联过程是亚氨基醚作为亲双烯体参与的罕见例子。
• 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。
• New synthesis of 3-amino-1H-benzo[f]chromene-2-carbonitriles
  作者：D. V. Osipov、V. A. Osyanin、Yu. N. Klimochkin

  DOI：10.1134/s1070428013030147

  日期：2013.3

  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.
• 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.