N,N-dibutylformamide dimethyl acetal | 19449-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 原羧酸衍生物
• 英文名称: N,N-dibutylformamide dimethyl acetal
• 英文别名: N,N-di-n-butylformamide dimethyl acetal；dibutylformamide dimethylacetal；N,N-dibutylaminomethylidene dimethyl acetal；N-butyl-N-(dimethoxymethyl)butan-1-amine
• CAS: 19449-30-0
• 化学式: C₁₁H₂₅NO₂
• 分子量: 203.325
• InChiKey: ILWAGGBLQBWJRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dibutylformamide dimethyl acetal 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 6-N-((di-n-butylamino)-methylene)-2'-O-tert-butyldimethylsilyl-5'-O-(4,4'-dimethoxytrityl)-L-cytidine
  参考文献：
  名称：

  Synthesis and Enzymatic Digestion of an RNA Nonamer in Both Enantiomeric Forms

  摘要：

  The D- and L-RNA nonamers of the sequence r(GCUUCGGC)T have been synthesised for X-ray crystallographic purposes. In vitro digestion of the unnatural optical antipode by snake venom phosphodiesterase I takes place at an approximately 1800-fold slower rate than that of the natural D-nonamer. The digestion experiments showed-to our knowledge for the first time-that L-RNA can indeed be cleaved enzymatically when phosphodiesterase I from snake venom is used-as opposed to a number of cellular ribonucleases-which sheds an interesting light on the evolution and possibly structure/function relationship of venom versus cellular degradation enzymes. The broad substrate specificity of this enzyme could be taken advantage of to study and further optimise the resistance towards biodegradation of therapeutic L-RNA aptamers. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00046-6
• 作为产物：
  描述：

  N,N-二丁基甲酰胺 生成 N,N-dibutylformamide dimethyl acetal
  参考文献：
  名称：

  Bredereck,H. et al., Chemische Berichte, 1968, vol. 101, p. 41 - 50

  摘要：

  DOI：

文献信息

• 2-Aza-2′-deoxyadenosine: Synthesis, Base-Pairing Selectivity, and Stacking Properties of Oligonucleotides
  作者：Tamizi Sugiyama、Enno Schweinberger、Zygmunt Kazimierczuk、Natalya Ramzaeva、Helmut Rosemeyer、Frank Seela

  DOI：10.1002/(sici)1521-3765(20000117)6:2<369::aid-chem369>3.0.co;2-2

  日期：2000.1.17

  2-Aza-2'-deoxyadenosine (2, z2Ad) is synthesized via its 1,N6-etheno derivative 7 and enzymatically deaminated to 2-aza-2'-deoxyinosine (3). Compound 2 is converted into the phosphoramidite building block 10b. This is employed in solid-phase oligonucleotide synthesis. The 2-azapurine base forms a strong base pair with guanine, but a much weaker one with adenine, thymine, and cytosine. Oligonucleotide

  2-Aza-2'-脱氧腺苷（2，z2Ad）是通过其1，N6-乙炔衍生物7合成的，并被酶法脱氨基形成2-aza-2'-脱氧肌苷（3）。化合物2被转化为亚磷酰胺结构单元10b。这用于固相寡核苷酸合成中。2-氮杂嘌呤碱基与鸟嘌呤形成强碱基对，而与腺嘌呤，胸腺嘧啶和胞嘧啶则弱得多。合成了在一个或两个末端带有悬空核苷酸残基的寡核苷酸双链体，例如2-aza-2'-脱氧腺苷和7-deaza-2'-脱氧腺苷（4，c7Ad），并且双链体的热稳定性为与悬挂的核苷酸残基的疏水性相关。
• Parallel-stranded oligonucleotide duplexes containing 5-methylisocytosine-guanine and isoguanine-cytosine base pairs
  作者：Frank Seela、Yang He、Changfu Wei

  DOI：10.1016/s0040-4020(99)00511-6

  日期：1999.7

  Parallel-stranded oligonucleotides containing 5-methylisocytosine-guanine and/or isoguanine-cytosine base pairs were prepared. The coupling efficiency was higher than 99% when the phosphoramidites of 2′-deoxy-5-methylisocytidine (2a) and of 2′-deoxyisoguanosine (3) were employed in solid-phase synthesis. The glycosylic bond of 2′-deoxy-5-methylisocytidine (1a) is stabilized against acid in the case

  制备包含5-甲基异胞嘧啶-鸟嘌呤和/或异鸟嘌呤-胞嘧啶碱基对的平行链寡核苷酸。当2'-脱氧-5-甲基异胞苷（2a）和2'-脱氧异鸟苷（3）的亚磷酰胺用于固相合成时，偶联效率高于99％。在am衍生物4a，b的情况下，2'-脱氧-5-甲基异胞苷（1a）的糖基键对酸稳定。长时间暴露于氨中会发生脱嘧啶作用。使用the准分子荧光明确确定了平行链（ps）双链体的取向。反平行（aps）双链体d（A 12）•d（T 12）（25•26当两个中心的腺嘌呤-胸腺嘧啶碱基对被异鸟嘌呤-胞嘧啶对取代时，变为平行方向。发现包含5-甲基异胞嘧啶-鸟嘌呤碱基对的ps-双链体的热稳定性显着低于具有异鸟嘌呤-胞嘧啶对的ps-双链体的热稳定性。根据CD光谱，与aps对应物相比，ps-DNA-DNA或DNA-RNA杂种在二级结构上表现出差异。
• Preparation of N-(alk-1-enyl) nucleobase compounds by Horner and Horner–Wadsworth–Emmons reactions
  作者：Thomas Boesen、Christian Madsen、Ulla Henriksen、Otto Dahl

  DOI：10.1039/b002744h

  日期：——

  A series of new N9-(alk-1-enyl)adenines and N1-(alk-1-enyl)thymines has been prepared by Horner reactions of the new phosphine oxides N9-(diphenylphosphorylmethyl)adenine and N1-(diphenylphosphorylmethyl)thymine derivatives 13a–c, or Horner–Wadsworth–Emmons reactions of the corresponding new phosphonates 14a–b, with benzaldehyde and various ketones. Yields were highest for the Horner reactions (10–79%), and were limited by steric hindrance, enolization of the ketones, and decomposition of some of the N1-(alk-1-enyl)thymines in the presence of excess base (NaH). Butanal gave mixtures of products under Horner conditions, probably because aldol reactions intervened.

  一系列新的N9-(烯-1-基)腺嘌呤和N1-(烯-1-基)胸腺嘧啶通过Horner反应制备，该反应以新的氧化膦衍生物N9-(二苯基膦酰甲基)腺嘌呤和N1-(二苯基膦酰甲基)胸腺嘧啶衍生物13a–c为原料，或者通过相应的新的膦酸酯14a–b与苯甲醛和各种酮进行Horner-Wadsworth-Emmons反应。Horner反应的产率最高（10-79%），但由于立体位阻、酮的烯醇化和在过量碱（NaH）存在下某些N1-(烯-1-基)胸腺嘧啶的分解，产率受到限制。正丁醛在Horner条件下产生混合产物，可能是因为发生了醇醛反应。
• Practical synthesis of N-(di-n-butylamino)methylene-protected 2-aminopurine riboside phosphoramidite for RNA solid-phase synthesis
  作者：Eva Neuner、Ronald Micura

  DOI：10.1007/s00706-019-02502-7

  日期：2019.11

  properties of nucleic acids. In particular, thermodynamics and kinetics of RNA folding and RNA–ligand binding, as well as RNA catalytic activity are addressable by pursuing the Ap fluorescence signal in response to external stimuli. Site-specific incorporation of Ap into RNA is usually achieved by RNA solid-phase synthesis and requires appropriately functionalized Ap riboside building blocks. Here

  2-氨基嘌呤 (Ap) 是一种荧光核碱基类似物，经常用作结构敏感报告基因来研究核酸的化学和生物物理特性。特别是，RNA 折叠和 RNA-配体结合的热力学和动力学以及 RNA 催化活性可以通过追踪响应外部刺激的 Ap 荧光信号来解决。Ap 位点特异性掺入 RNA 通常是通过 RNA 固相合成实现的，并且需要适当功能化的 Ap 核苷构建模块。在这里，我们介绍了一种 2-氨基嘌呤核苷亚磷酰胺的稳健合成路径，其 N 2官能团被N- (二正丁基氨基)亚甲基掩蔽。这种保护被认为优于先前描述的N- (二甲氨基)亚甲基或酰基保护模式，所述模式需要微调脱保护条件来获得大的合成RNA。 图文摘要
• New Base Pairing Motifs. The Synthesis and Thermal Stability of Oligodeoxynucleotides Containing Imidazopyridopyrimidine Nucleosides with the Ability to Form Four Hydrogen Bonds
  作者：Noriaki Minakawa、Naoshi Kojima、Sadao Hikishima、Takashi Sasaki、Arihiro Kiyosue、Naoko Atsumi、Yoshihito Ueno、Akira Matsuda

  DOI：10.1021/ja0347686

  日期：2003.8.1

  The synthesis and thermal stability of oligodeoxynucleotides (ODNs) containing imidazo[5',4':4,5]pyrido[2,3-d]pyrimidine nucleosides 1-4 (N(N), O(O), N(O), and O(N), respectively) with the aim of developing two sets of new base pairing motifs consisting of four hydrogen bonds (H-bonds) is described. The proposed four tricyclic nucleosides 1-4 were synthesized through the Stille coupling reaction of

  含有咪唑并[5',4':4,5]吡啶并[2,3-d]嘧啶核苷1-4 (N(N), O(O), N(O)的寡聚脱氧核苷酸 (ODN) 的合成和热稳定性) 和 O(N))，目的是开发两组由四个氢键（H 键）组成的新碱基配对基序。提出的四种三环核苷 1-4 是通过 5-碘咪唑核苷与合适的 5-甲锡烷基嘧啶衍生物的 Stille 偶联反应合成的，然后进行分子内环化。这些核苷被纳入 ODN 以研究 H 键合能力。当一个分子的三环核苷结合到每个 ODN（ODN I 和 II，每个 17mer）的中心时，没有观察到明显的碱基配对特异性，并且所有双链体都比含有天然 G:C 和 A:T 对的双链体更不稳定。另一方面，当三个三环核苷分子连续掺入每个 ODN（ODN III 和 IV，每个 17 聚体）的中心时，由于特定的碱基配对，观察到双链体的热和热力学稳定性。含有 N(O):O(N) 对的双链体的熔解温度 (T(m))