2-amino-9-[2-(4,8-di-tert-butyl-2,10-dimethyl-6-oxo-12H-5,7-dioxa-6λ⁵-phospha-dibenzo[a,d]cycloocten-6-yl)-1-methyl-vinyl]-1,9-dihydro-purin-6-one

• 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: 2-amino-9-[2-(4,8-di-tert-butyl-2,10-dimethyl-6-oxo-12H-5,7-dioxa-6λ⁵-phospha-dibenzo[a,d]cycloocten-6-yl)-1-methyl-vinyl]-1,9-dihydro-purin-6-one
• 英文别名: 2-amino-9-[(E)-1-(1,9-ditert-butyl-3,7-dimethyl-11-oxo-5H-benzo[d][1,3,2]benzodioxaphosphocin-11-yl)prop-1-en-2-yl]-1H-purin-6-one
• 化学式: C₃₁H₃₈N₅O₄P
• 分子量: 575.648
• InChiKey: SCXPIYILUIDJSG-XDJHFCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,8-di-tert-butyl-2,10-dimethyl-6-propa-1,2-dienyl-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-oxide 、 鸟嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到2-amino-9-[2-(4,8-di-tert-butyl-2,10-dimethyl-6-oxo-12H-5,7-dioxa-6λ⁵-phospha-dibenzo[a,d]cycloocten-6-yl)-1-methyl-vinyl]-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  烯丙基膦酸酯的新型胺/核碱基加成产物的合成与应用

  摘要：

  在烯丙基膦酸酯与胺/核碱基的反应中，取决于胺和烯丙基膦酸酯，分离出Z-或E-乙烯基膦酸酯或烯丙基膦酸酯作为具有β-氨基官能团的单一异构体。到膦酸酯的简单路线与β-NH 2基团通过与氨直接反应的发展。在与腺嘌呤的反应中，观察到三种不同的反应模式，其中一种涉及异常环化。由此证明，通过霍纳-沃兹沃思-埃蒙斯（HWE）反应合成（烯胺基）-1,3-丁二烯时得到的（烯胺基）烯丙基膦酸酯产品也很有用。

  DOI：

  10.1016/j.tet.2006.08.034

文献信息

• Synthesis and utility of new amine/nucleobase addition products of allenylphosphonates
  作者：K.C. Kumara Swamy、E. Balaraman、N. Satish Kumar

  DOI：10.1016/j.tet.2006.08.034

  日期：2006.10

  In the reaction of allenylphosphonates with amines/nucleobases, depending on the amine and the allenylphosphonate, either Z- or E-vinylphosphonate or allylphosphonate as a single isomer with a β-amino functionality was isolated. A simple route to phosphonates with a β-NH2 group is developed by direct reaction with ammonia. In reactions with adenine, three different modes of reaction, with one of them involving

  在烯丙基膦酸酯与胺/核碱基的反应中，取决于胺和烯丙基膦酸酯，分离出Z-或E-乙烯基膦酸酯或烯丙基膦酸酯作为具有β-氨基官能团的单一异构体。到膦酸酯的简单路线与β-NH 2基团通过与氨直接反应的发展。在与腺嘌呤的反应中，观察到三种不同的反应模式，其中一种涉及异常环化。由此证明，通过霍纳-沃兹沃思-埃蒙斯（HWE）反应合成（烯胺基）-1,3-丁二烯时得到的（烯胺基）烯丙基膦酸酯产品也很有用。
• Alkynyl and Phosphonyl Substituted Nucleobases: A Case of Thermally Induced Conformational Polymorphism
  作者：K. C. Kumara Swamy、Srinivasarao Allu、Venu Srinivas、E. Balaraman、K. V. P. Pavan Kumar

  DOI：10.1021/cg101737x

  日期：2011.6.1

  Substituted nucleobases with alkynyl and phosphonyl groups wire investigated in the context of supramolecular interactions and possible use toward synthesis of nucleoside phosphonic acids (NPAs). The adeninyl compound (adeninyl-N-9)-CH2CH2CH2CH2C CH exhibits conformational polymorphism as revealed by X-ray structures determined at 200 and 298 K. Interestingly, in the compound (adeninyl-N-9)-(CH2)(15)CH3, the long aliphatic carbon chain does not show disorder. A rather unusual bending of alkyl chain, likely due to C center dot center dot center dot O interactions, is observed in the case of the thymine compound (thyminyl)-CH2CH2CH2C CH that possesses a terminal alkyne group. The, powerful hydrogen bond acceptor property of the phosphoryl oxygen (P=O) does not perturb (unless assisted by other hydrogen Bonding partners) the :homo base-pairing in the structures of most of the phosphonyl substituted nucleobases studied.