2-[cyclohexyl(methyl)amino]-5-nitrobenzaldehyde | 34601-38-2

• 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: 2-[cyclohexyl(methyl)amino]-5-nitrobenzaldehyde
• 英文别名: 2-(N-Methyl-N-cyclohexyl)amino-5-nitrobenzaldehyd
• CAS: 34601-38-2
• 化学式: C₁₄H₁₈N₂O₃
• mdl: MFCD07687331
• 分子量: 262.309
• InChiKey: OOYMKDNVQYYCNI-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C(Solv: isopropanol (67-63-0))
• 沸点：
  424.3±35.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[cyclohexyl(methyl)amino]-5-nitrobenzaldehyde 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(benzothiazol-2-yl)-1-methyl-6-nitro-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitrile
  参考文献：
  名称：

  A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes

  摘要：

  An interaction of 2-[cyclohexyl(methyl)amino]benzaldehydes with substituted acetonitriles X-CH2CN (X=CN, Tos, hetaryl) was found to yield 1-methyl-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitriles. The corresponding spiroquinoline-2,1'-cyclopentane analogues were obtained similarly starting from 2-[cyclopentyl(methyl)amino]benzaldehydes. The reaction was assumed to proceed via initial Knoevenagel condensation and further ring closure of the formed adduct according to the tert-amino effect mechanism. The structure of the prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.042
• 作为产物：
  描述：

  N-甲基环己胺 、 2-氯-5-硝基苯甲醛 在 碳酸氢钠 作用下， 以 环丁砜 为溶剂， 生成 2-[cyclohexyl(methyl)amino]-5-nitrobenzaldehyde
  参考文献：
  名称：

  杂环化合物的合成。第二十四部分。用邻位取代的芳基卡宾和芳基亚硝烯前体进行环化研究

  摘要：

  邻二烷基氨基取代的苯甲醛的甲苯磺酰的热分解和光分解产生二氢吲哚。已经探索了这种环化的范围和机理。此外，苯甲醛甲苯磺酰腙与ø -烷氧基- ，ø -thioalkyl-，和ø -膦取代基以及相应的重氮烷进行热解和光解。从这些前体的碳烯的产物与来自类似的氮宾的前体[获得的那些进行比较即ARN 3或ARNO 2 +（RO）3 P]。

  DOI：

  10.1039/j39710003693

文献信息

• Syntheses of heterocyclic compounds. Part XXIV. Cyclisation studies with ortho-substituted arylcarbene and arylnitrene precursors
  作者：G. V. Garner、D. B. Mobbs、H. Suschitzky、J. S. Millership

  DOI：10.1039/j39710003693

  日期：——

  indolines. The scope and mechanism of this cyclisation have been explored. Moreover, benzaldehyde tosylhydrazones with o-alkoxy-, o-thioalkyl-, and o-phosphonate substituents as well as the corresponding diazoalkanes were pyrolysed and photolysed. The products from these carbene precursors were compared with those obtained from the analogous nitrene precursors [i.e. ArN3 or ArNO2+(RO)3P].

  邻二烷基氨基取代的苯甲醛的甲苯磺酰的热分解和光分解产生二氢吲哚。已经探索了这种环化的范围和机理。此外，苯甲醛甲苯磺酰腙与ø -烷氧基- ，ø -thioalkyl-，和ø -膦取代基以及相应的重氮烷进行热解和光解。从这些前体的碳烯的产物与来自类似的氮宾的前体[获得的那些进行比较即ARN 3或ARNO 2 +（RO）3 P]。
• A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes
  作者：Anton V. Tverdokhlebov、Alexander P. Gorulya、Andrey A. Tolmachev、Alexander N. Kostyuk、Alexander N. Chernega、Eduard B. Rusanov

  DOI：10.1016/j.tet.2006.07.042

  日期：2006.9

  An interaction of 2-[cyclohexyl(methyl)amino]benzaldehydes with substituted acetonitriles X-CH2CN (X=CN, Tos, hetaryl) was found to yield 1-methyl-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitriles. The corresponding spiroquinoline-2,1'-cyclopentane analogues were obtained similarly starting from 2-[cyclopentyl(methyl)amino]benzaldehydes. The reaction was assumed to proceed via initial Knoevenagel condensation and further ring closure of the formed adduct according to the tert-amino effect mechanism. The structure of the prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2006 Elsevier Ltd. All rights reserved.