(2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(2,3,4-trifluoro-phenyl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene | 705281-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(2,3,4-trifluoro-phenyl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene
• CAS: 705281-28-3
• 化学式: C₂₃H₃₇F₃O₄Si₂
• 分子量: 490.711
• InChiKey: IWKUAJSQMXKYNQ-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(2,3,4-trifluoro-phenyl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene 在 吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,3,4-trifluoro-phenyl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Efforts To Expand the Genetic Alphabet:  Identification of a Replicable Unnatural DNA Self-Pair

  摘要：

  Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.

  DOI：

  10.1021/ja049961u
• 作为产物：
  描述：

  2,3,4-三氟溴苯 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.67h， 生成 (2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(2,3,4-trifluoro-phenyl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene
  参考文献：
  名称：

  Efforts To Expand the Genetic Alphabet:  Identification of a Replicable Unnatural DNA Self-Pair

  摘要：

  Six unnatural nucleotides featuring fluorine-substituted phenyl nucleobase analogues have been synthesized, incorporated into DNA, and characterized in terms of the structure and replication properties of the self-pairs they form. Each unnatural self-pair is accommodated in B-form DNA without detectable structural perturbation, and all are thermally stable and selective to roughly the same degree. Furthermore, the efficiency of polymerase-mediated mispair synthesis is similar for each unnatural nucleotide in the template. In contrast, the efficiency of polymerase-mediated self-pair extension is highly dependent on the specific fluorine substitution pattern. The most promising unnatural base pair candidate of this series is the 3-fluorobenzene self-pair, which is replicated with reasonable efficiency and selectivity.

  DOI：

  10.1021/ja049961u