9-(10-bromodecyl)adenine | 186127-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(10-bromodecyl)adenine
• 英文别名: 9-(10-Bromodecyl)purin-6-amine
• CAS: 186127-54-8
• 化学式: C₁₅H₂₄BrN₅
• 分子量: 354.293
• InChiKey: FWSFETAZULBNFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  508.6±53.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(10-bromodecyl)adenine 在 Sodium thiosulfate pentahydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以57%的产率得到S-(10-(6-amino-9H-purin-9-yl)decyl) O-hydrogen sulfurothioate
  参考文献：
  名称：

  Self-Assembled Monolayers of Double-Chain Disulfides of Adenine on Au: An IR-UV Sum-Frequency Generation Spectroscopic Study

  摘要：

  We have synthesized double-chain disulfides of adenine with different chain lengths (n = 2,4, 5, 9, and 10) and studied their self-assembled monolayers (SAM) oil gold surface by IR-UV doubly resonant sum frequency generation spectroscopy with the help of DFT calculation. A versatile way to investigate the orientation angle of functional groups of SAMs and their surface coverage has been demonstrated, It was revealed that the I R dipoles of the band at around 1630 cm(-1), which were almost parallel to the long molecular axis of the adenine ring, were less tilted with respect to the substrate surface in the SAMs with longer chains (n = 9 and W) in comparison to those with shorter chains (n = 2, 4, and 5).

  DOI：

  10.1021/la9021992
• 作为产物：
  描述：

  1,10-二溴癸烷 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以28%的产率得到9-(10-bromodecyl)adenine
  参考文献：
  名称：

  NMR study of 9,9′-(alkane-α,ω-diyl)diadenine

  摘要：

  The relationship between NMR chemical shifts of adenine ring protons of low concentrations of 9,9'-(alkane-alpha,omega-diyl)diadenine and the length of the polymethylene chains has been investigated in buffer solutions at pD 1.0, 7.0 and 13.0 and in organic solvents such as CD3OD, (CF3)(2)CDOD, [H-2(6)]dimethyl sulfoxide and CF3COOD. The chemical shifts were compared with those of 9-(omega-bromoalkyl)adenine.

  DOI：

  10.1039/p29960002695

文献信息

• Molecular assemblies of bis- and tris-adenine derivatives
  作者：Toshio Itahara、Tomohide Uto、Miho Sunose、Takehiko Ueda

  DOI：10.1016/s0022-2860(02)00337-x

  日期：2002.10

  Abstract Molecular assemblies of bis- and tris-adenine derivatives were studied by means of NMR, IR, and DSC. Mixtures of the adenine derivatives and 1-hexadecylthymine showed multiple phase transitions in the temperature range of the solid phase. A difference of the NMR, IR, and DSC data between bis-adenine and tris-adenine derivatives may be attributable to a formation of intramolecular hydrogen

  摘要 利用NMR、IR和DSC研究了双腺嘌呤和三腺嘌呤衍生物的分子组装。腺嘌呤衍生物和 1-十六烷基胸腺嘧啶的混合物在固相温度范围内表现出多重相变。双腺嘌呤和三腺嘌呤衍生物之间 NMR、IR 和 DSC 数据的差异可能归因于分子内氢键的形成。
• NMR study of stacking interactions between adenine and xanthine rings
  作者：Toshio Itahara

  DOI：10.1039/a708866c

  日期：——

  A relationship between the chemical shifts of adenine and xanthine ring protons of 7-[ω-(6-aminopurin-9-yl)alkyl]-1,3-dimethylxanthines (1) and the number of carbons (n = 2–10) in their polymethylene chains has been compared with that of 1-[ω-(6-aminopurin-9-yl)alkyl]-3,7-dimethylxanthines (2) in the buffer solutions at pD 7.0, 1.0 and 13.0 and in organic solvents. The relationship of 1 is clearly distinct from that of 2. The concentration dependence and the effects of temperature on the chemical shifts of 1 and 2 have also been investigated. While the upfield shifts of the ring protons of 1 and 2 in the buffer solutions at pD 7.0 and 13.0 are explained in terms of stacking interactions between adenine and xanthine rings, the results in the buffer solution at pD 1.0 may be due to cation–π interactions. On the basis of these data, it can be assumed that the stacking interactions do not only consist of interactions between adenine and xanthine rings.

  比较了 7-[ω-(6-氨基嘌呤-9-基)烷基]-1,3-二甲基黄嘌呤（1）与 1-[ω-(6-氨基嘌呤-9-基)烷基]-3,7-二甲基黄嘌呤（2）在 pD 7.0、1.0 和 13.0 的缓冲溶液中以及在有机溶剂中的腺嘌呤环和黄嘌呤环质子的化学位移与其聚亚甲基链中碳原子数（n = 2-10）之间的关系。此外，还研究了浓度依赖性和温度对 1 和 2 化学位移的影响。在 pD 值为 7.0 和 13.0 的缓冲溶液中，1 和 2 的环质子的上场移位可以用腺嘌呤环和黄嘌呤环之间的堆叠相互作用来解释，而在 pD 值为 1.0 的缓冲溶液中的结果则可能是阳离子-π 相互作用所致。根据这些数据可以推测，堆积相互作用不仅包括腺嘌呤环和黄嘌呤环之间的相互作用。
• Self-Assembled Monolayers of Double-Chain Disulfides of Adenine on Au: An IR-UV Sum-Frequency Generation Spectroscopic Study
  作者：Tetsuhiko Nagahara、Takumi Suemasu、Misako Aida、Taka-aki Ishibashi

  DOI：10.1021/la9021992

  日期：2010.1.5

  We have synthesized double-chain disulfides of adenine with different chain lengths (n = 2,4, 5, 9, and 10) and studied their self-assembled monolayers (SAM) oil gold surface by IR-UV doubly resonant sum frequency generation spectroscopy with the help of DFT calculation. A versatile way to investigate the orientation angle of functional groups of SAMs and their surface coverage has been demonstrated, It was revealed that the I R dipoles of the band at around 1630 cm(-1), which were almost parallel to the long molecular axis of the adenine ring, were less tilted with respect to the substrate surface in the SAMs with longer chains (n = 9 and W) in comparison to those with shorter chains (n = 2, 4, and 5).
• NMR study of 9,9′-(alkane-α,ω-diyl)diadenine
  作者：Toshio Itahara

  DOI：10.1039/p29960002695

  日期：——

  The relationship between NMR chemical shifts of adenine ring protons of low concentrations of 9,9'-(alkane-alpha,omega-diyl)diadenine and the length of the polymethylene chains has been investigated in buffer solutions at pD 1.0, 7.0 and 13.0 and in organic solvents such as CD3OD, (CF3)(2)CDOD, [H-2(6)]dimethyl sulfoxide and CF3COOD. The chemical shifts were compared with those of 9-(omega-bromoalkyl)adenine.