2-(dimethylamino)-8-isopropyl-5-methyl-4-oxo-4H-1-benzopyran-3-carbaldehyde | 131335-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(dimethylamino)-8-isopropyl-5-methyl-4-oxo-4H-1-benzopyran-3-carbaldehyde
• 英文别名: 2-(Dimethylamino)-5-methyl-4-oxo-8-propan-2-ylchromene-3-carbaldehyde
• CAS: 131335-06-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: CFIAUSSUWKRSBT-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  463.4±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(dimethylamino)-8-isopropyl-5-methyl-4-oxo-4H-1-benzopyran-3-carbaldehyde 在 盐酸羟胺 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 、 水 为溶剂， 反应 0.83h， 生成 3-ciano-2-(dimetilammino)-8-isopropil-5-metilcromone
  参考文献：
  名称：

  Balbi; Roma; Mazzei, Il Farmaco, 1989, vol. 44, # 6, p. 565 - 577

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N,N’,N’-四甲基丙二酰胺 在 三氯氧磷 作用下， 反应 8.0h， 生成 2-(dimethylamino)-8-isopropyl-5-methyl-4-oxo-4H-1-benzopyran-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆

  摘要：

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.030

文献信息

• Synthesis of 2-[(3-aminoalkyl or 3-bromoalkyl)amino]-4H-1-benzopyran-4-one derivatives
  作者：Enzo Sottofattori、Teresa Grandi、Alessandro Balbi

  DOI：10.1016/0040-4039(94)02469-r

  日期：1995.2

  The title compounds were advantageously synthesized from 2-(dialkylamino)chromones and 1,3-diaminopropane (or 1-amino-3-bromopropane) by amine exchange. The 3-cyano derivatives 5 were directly prepared from 2-(dimethylamino)chromones 1 and KCN by nitro displacement.
• Amine Exchange and Unexpected Ring-Opening Reactions of Pyranone Derivatives: Synthesis of 3-Amino-Substituted Oxonaphthopyran-carbaldehydes and Tetrahydropyrimidinethanones as New Potential Oligonucleotide Stabilization Agents
  作者：Enzo Sottofattori、Maria Anzaldi、Alessandro Balbi、Roberto Artali、Gabriella Bombieri

  DOI：10.1002/1522-2675(200206)85:6<1698::aid-hlca1698>3.0.co;2-b

  日期：2002.6

  3-[(3-Aminopropyl)amino]-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde (10) was synthesized by nucleophilic substitution reaction of 2-(3-dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde (9) and the monoprotected propane-1,3-diamine. The reaction with the unprotected reagent led to the unexpected 1-(2-hydroxynaphthalen-1-yl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethanone (6). Extension of this reaction to chromone 16 gave 1-(2-hydroxy-3-isopropyl-6-methylphenyl) -2- (tetrahydropyrimidin-2(1H)-ylidene)ethanone (7). The X-ray crystal structures of 6 and 7 were also determined.
• BALBI, A.;ROMA, G.;MAZZE, M.;SOTTOFATTORI, E.;CADEL, S.;SCHIANTARELLI, P., FARMACO, 44,(1989) N, C. 565-577
  作者：BALBI, A.、ROMA, G.、MAZZE, M.、SOTTOFATTORI, E.、CADEL, S.、SCHIANTARELLI, P.

  DOI：——

  日期：——
• Balbi; Roma; Mazzei, Il Farmaco, 1989, vol. 44, # 6, p. 565 - 577
  作者：Balbi、Roma、Mazzei、Sottofattori、Cadel、Schiantarelli

  DOI：——

  日期：——
• Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆
  作者：Enzo Sottofattori、Maria Anzaldi、Mauro Mazzei、Mariangela Miele、Alessandro Balbi、Dmitri S. Pyshnyi、Olga D. Zakharova、Tatyana V. Abramova

  DOI：10.1016/j.bmc.2004.12.030

  日期：2005.3.1

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.