2-[环己基(甲基)氨基]苯甲醛 | 104524-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[环己基(甲基)氨基]苯甲醛
• 中文别名: 苯(甲)醛,2-(环己基甲基氨基)-
• 英文名称: 2-[cyclohexyl(methyl)amino]benzaldehyde
• 英文别名: 2-(N-Cyclohexyl-N-methyl-amino)benzaldehyde
• CAS: 104524-84-7
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: JIPSDUHTLBEVSA-UHFFFAOYSA-N

物化性质

• 沸点：
  343.7±15.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[环己基(甲基)氨基]苯甲醛 、 4-甲苯磺酰乙腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 以95%的产率得到1-methyl-3-[(4-methylphenyl)sulfonyl]-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-氟苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以63%的产率得到2-[环己基(甲基)氨基]苯甲醛
  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

文献信息

• Diastereoselective Spirocyclization via Intramolecular C( <i>sp</i> ³ )−H Bond Functionalization Triggered by Sequential [1,5]‐Hydride Shift/Cyclization Process: Approach to Spiro‐tetrahydroquinolines
  作者：Arup Bhowmik、Sumit Das、Writhabrata Sarkar、K. M. Saidalavi、Aniket Mishra、Anupama Roy、Indubhusan Deb

  DOI：10.1002/adsc.202001011

  日期：2021.2.2

  functionalization triggered by sequential [1,5]‐ hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2‐coumaranone, 4‐hydroxycoumarin, 3‐coumaranone, and 3‐isochromanone. This protocol provides a Lewis acid catalyst‐free straight forward one‐pot reaction in cases of 2‐coumaranone and 4‐hydroxycoumarin, Lewis acid‐catalyzed stepwise reaction for 3‐coumaranone

  通过邻氨基苯甲醛和活性亚甲基化合物等连续的[1,5]-氢化物转移/环化序列引发的C（sp 3）-H键官能化，开发了螺[5.5]和[5.4]-四氢喹啉的直接合成物作为2-香豆酮，4-羟基香豆素，3-香豆酮和3-异苯并二氢吡喃酮。该方案可在2-香豆香酮和4-羟基香豆素的情况下提供无Lewis酸的简单直接反应，而Lewis酸催化的3-香豆香酮和3-isochromanone的逐步反应可在其中使用广泛的螺杂环优异的良率和非对映选择性。
• Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors
  申请人：FISONS plc

  公开号：EP0174717B1

  公开（公告）日：1992-01-22
• 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.