3-(dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde | 55841-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-(dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde
• 英文别名: 3-dimethylamino-1-oxo-1H-benzo[f]chromene-2-carbaldehyde；3-(Dimethylamino)-1-oxobenzo[f]chromene-2-carbaldehyde
• CAS: 55841-04-8
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: QWMRJAVQVOJXQT-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C(Solv: benzene (71-43-2))
• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 生成 3-[(3-aminopropyl)amino]-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde hydrochloride
  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
• 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 9.0h， 生成 3-(dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-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

• Naphtho[1′,2′:5,6]pyrano[2,3-6][1,5]benzodiazepine Derivatives
  作者：Giorgio Roma、Aldo Ermili、Alessandro Balbi、Elda Massa、Mario Di Braccio

  DOI：10.1002/jhet.5570180827

  日期：1981.12

  3-(dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde (Ia) with o-phenylenediamines or N-monosubstituted o-phenylenediamines in refluxing glacial acetic acid afforded the corresponding naphtho[1′,2′:5,6]pyrano[2,3-b][1,5]benzodiazepin-15-(8H)ones V in very good yields. A similar result was achieved when the reaction was carried out in refluxing pyridine, using N-monosubstituted o-phenylenediamine

  3-（二甲基氨基）-1-氧代-1 H-萘[ 2,1- b ]吡喃-2-甲醛（Ia）与邻苯二胺或N-单取代邻苯二胺在回流的冰醋酸中反应得到相应的萘并[1'，2'：5,6]吡喃并[2,3- b ] [1,5]苯并二氮杂-15-15-（8 H）酮V非常高的收率。当使用N-单取代的邻苯二胺盐酸盐在吡啶中回流进行反应时，获得了相似的结果。重要中间体的分离以及通过不同的单链途径的合成证实了化合物V的结构。
• Naphtho[1′,2′:5,6] pyrano[2,3-<i>c</i>] pyrazole derivatives
  作者：Giorgio Roma、Aldo Ermili、Mauro Mazzei

  DOI：10.1002/jhet.5570120106

  日期：1975.2

  Reaction of 1-oxo-3-dialkylamino-1 H-naphtho[2,1-b]pyrans with N,N-dimethylformamide in the presence of phosphorus oxychloride afforded the corresponding 1-oxo-2-formyl-3-dialkyl-amino-1H-naphtho[2,1-b]pyrans.

  1-氧代-3-二烷基氨基-1 H-萘并[2,1- b ]吡喃与N，N-二甲基甲酰胺在三氯氧磷存在下反应，得到相应的1-氧代-2-甲酰基-3-二烷基-氨基-1 H-萘并[2,1 -b ]吡喃。
• Roma; Vigevani; Mazzei, Farmaco, Edizione Scientifica, 1977, vol. 32, # 1, p. 40 - 53
  作者：Roma、Vigevani、Mazzei、Ermili

  DOI：——

  日期：——
• Roma,G. et al., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 761 - 764
  作者：Roma,G. et al.

  DOI：——

  日期：——
• 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.