2-(3-methoxyphenylamino)cyclohex-2-en-1-one | 1418129-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenylamino)cyclohex-2-en-1-one
• 英文别名: 2-(3-Methoxyanilino)cyclohex-2-en-1-one
• CAS: 1418129-49-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: RNPIGDZGMFQNMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenylamino)cyclohex-2-en-1-one 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.17h， 生成 1,7-dimethoxy-9H-carbazole
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175
• 作为产物：
  描述：

  间氨基苯甲醚 、 1,2-环己二酮 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到2-(3-methoxyphenylamino)cyclohex-2-en-1-one
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175

文献信息

• Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves
  作者：Weiwei Luo、Zhicheng Sun、E. H. Nisala Fernando、Vladimir N. Nesterov、Thomas R. Cundari、Hong Wang

  DOI：10.1039/d0sc02078h

  日期：——

  α-enaminones with quinones through facile manipulation of catalyst and additive, leading to structurally completely different products. The two divergent processes, which involve formal aza- and oxo-[3 + 2] cycloaddition reactions, are mediated by chiral phosphoric acid and molecular sieves, respectively. While inclusion of phosphoric acid in the reaction switched the reaction pathway to favor the

  通过催化剂和添加剂的简便操作，已开发出一种双发散方法，用于α-烯胺酮与醌的反应，从而得到结构上完全不同的产物。涉及正式氮杂和氧代-[3 + 2]环加成反应的两个发散过程分别由手性磷酸和分子筛介导。虽然在反应中加入磷酸会改变反应路径，从而有利于有效形成多种氮取代的吲哚，向反应中添加4Å分子筛，再次切换了反应路径，从而导致2,3-二氢苯并呋喃的对映选择性合成，在温和条件下具有优异的收率和对映选择性。这项工作的研究表明，手性磷酸的作用是降低过渡态能量，并促进形成正式氮杂-[3 + 2]环加成反应的酰胺中间体，而分子筛有助于促进质子向氧代[3+]的转移。 2]环加成。在这项工作中还公开了α-烯胺酮的反应性。
• Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C–C bond formation
  作者：Hao Shi、Tianjian Guo、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1016/j.tet.2014.02.083

  日期：2014.4

  A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2-enone with hypervalent iodine reagent PhI(OCOCF3)2 (FIFA), through a direct intramolecular oxidative C(sp(2))-C(sp(2)) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]lindol-6(5H)-one skeletons. The mechanism of the process was proposed and briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.