N-[(1S,2R,5R)-2-hydroxy-5-(9-phenylxanthen-9-yl)oxycyclopentyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide | 673458-65-6

• 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: N-[(1S,2R,5R)-2-hydroxy-5-(9-phenylxanthen-9-yl)oxycyclopentyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide
• CAS: 673458-65-6
• 化学式: C₃₁H₂₉N₃O₆
• 分子量: 539.588
• InChiKey: VWOUNVBUAAWIPF-RJRADHEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  122.65
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 N-[(1S,2R,5R)-2-hydroxy-5-(9-phenylxanthen-9-yl)oxycyclopentyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到N-[(1R,2R,5R)-2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-5-(9-phenylxanthen-9-yl)oxycyclopentyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of a Cyclopentane Amide DNA Analogue and Its Base Pairing Properties

  摘要：

  cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodcoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4degreesC/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible.

  DOI：

  10.1081/ncn-120022837
• 作为产物：
  描述：

  (2-环戊烯-1-氧基)二甲基(1,1-二甲基乙基)硅烷 在 palladium on activated charcoal 吡啶 、 porcine liver esterase 、 4-二甲氨基吡啶 、 氢氧化钾 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N-[(1S,2R,5R)-2-hydroxy-5-(9-phenylxanthen-9-yl)oxycyclopentyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of a Cyclopentane Amide DNA Analogue and Its Base Pairing Properties

  摘要：

  cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodcoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4degreesC/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible.

  DOI：

  10.1081/ncn-120022837