1-(2-hydroxy-4,5-dimethylphenyl)-N,N,N-trimethylmethane ammonium iodide | 1210475-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-hydroxy-4,5-dimethylphenyl)-N,N,N-trimethylmethane ammonium iodide
• 英文别名: 2-[(dimethylamino)methyl]-4,5-dimethylphenol iodomethylate；(2-Hydroxy-4,5-dimethylphenyl)-N,N,N-trimethylmethanaminium iodide；(2-hydroxy-4,5-dimethylphenyl)methyl-trimethylazanium;iodide
• CAS: 1210475-90-3
• 化学式: C₁₂H₂₀NO*I
• 分子量: 321.201
• InChiKey: XQBKFRHIUXBEPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4,5-dimethylphenyl)-N,N,N-trimethylmethane ammonium iodide 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 锌 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 3-(2-hydroxy-4,5-dimethylphenyl)-1-phenylpropan-1-one
  参考文献：
  名称：

  2-芳酰基-2,3-二氢苯并呋喃还原重排为2-羟基二氢查尔酮和黄酮-2-烯

  摘要：

  提出了通过邻醌甲基化物和吡啶鎓叶立德的形式 [4+1] 环加成反应然后还原重排合成 2-芳基和 2,4-二芳基取代的 4 H-色烯的两步程序。 2-芳酰基-2,3-二氢苯并呋喃通过乙酸中的锌或钐和 1,4-二恶烷中的三甲基氯硅烷的作用。通过乙酸中锌的作用还原 3-未取代的 2-芳酰基-2,3-二氢苯并呋喃主要产生 2-羟基二氢查耳酮。

  DOI：

  10.1007/s10593-021-03039-6

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。
• Reactions of o-Quinone Methides with Halogenated 1H-Azoles: Access to Benzo[e]azolo[1,3]oxazines
  作者：Vitaly Osyanin、Dmitry Osipov、Leonid Voskressensky、Yuri Klimochkin

  DOI：10.1055/s-0036-1588411

  日期：——

  and intramolecular nucleophilic substitution. A simple route to the series of azolo-condensed benzo[e][1,3]oxazines such as 9H-benzo[e][1,2,4]triazolo[5,1-b][1,3]oxazines, 9H-benzo[e]pyrazolo[5,1-b][1,3]oxazines, and 5H-benzo[e]imidazo[2,1-b][1,3]oxazines has been developed. The reaction proceeds through formation of an ortho-quinone methide intermediate followed by aza-Michael addition of the halogenoazoles

  摘要 一系列偶氮缩合的苯并[ e ] [1,3]恶嗪如9 H-苯并[ e ] [1,2,4]三唑[5,1- b ] [1,3]恶嗪的简单途径已经开发了9 H-苯并[ e ]吡唑并[5,1- b ] [1,3]恶嗪和5 H-苯并[ e ]咪唑并[2,1- b ] [1,3]恶嗪。该反应通过形成邻-醌甲基化物中间体，然后将卤代唑的氮杂-迈克尔加成至邻-醌甲基化物和分子内亲核取代来进行。 一系列偶氮缩合的苯并[ e ] [1,3]恶嗪如9 H-苯并[ e ] [1,2,4]三唑[5,1- b ] [1,3]恶嗪的简单途径已经开发了9 H-苯并[ e ]吡唑并[5,1- b ] [1,3]恶嗪和5 H-苯并[ e ]咪唑并[2,1- b ] [1,3]恶嗪。该反应通过形成邻-醌甲基化物中间体，然后将卤代唑的氮杂-迈克尔加成至邻-醌甲基化物和分子内亲核取代来进行。
• Convenient one-step synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles and 5-unsubstituted 5H-chromeno[2,3-b]pyridine-3-carbonitriles from quaternary ammonium salts
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1016/j.tet.2012.04.065

  日期：2012.7

  We have reported DBU catalyzed synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles in water under reflux. The attractive features of this process are mild reaction conditions, short reaction times, easy isolation of products and good yields. 5H-chromeno[2,3-b]pyridine-3-carbonitriles were obtained by refluxing excess of malononitrile and quaternary ammonium salts in ethanol in the presence

  我们已经报道了DBU在回流下在水中催化4-未取代的2-氨基-4 H-亚甲基-2-腈的合成。该方法的吸引人的特征是反应条件温和，反应时间短，产物易于分离和产率高。在NaOH为催化剂的情况下，通过将过量的丙二腈和季铵盐在乙醇中回流，得到5 H -chromeno [2,3 - b ]吡啶-3-腈。据信这些反应的机理涉及邻醌甲基化物中间体的形成。
• Synthesis of the new heterocyclic system, indolo[2,1-b]benzoxazine
  作者：V. A. Osyanin、Yu. N. Klimochkin

  DOI：10.1007/s10593-009-0350-3

  日期：2009.7

  The previously unknown heterocyclic system, indolo[2,1-b][1,3]benzoxazine, has been synthesized by condensation of iodomethylates of 2-[(dimethylamino)methylphenols] and 2-bromomelatonins. The highly reactive o-methylenequinone is proposed as an intermediate.

  先前未知的杂环系统吲哚并[2,1- b ] [1,3]苯并恶嗪是通过2-[（二甲基氨基）甲基苯酚]和2-溴褪黑激素的碘甲基酯缩合合成的。提出了高反应性的邻亚甲基醌作为中间体。