5-chloro-8-quinolyl phosphate | 71933-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-8-quinolyl phosphate
• 英文别名: (5-Chloroquinolin-8-yl) dihydrogen phosphate
• CAS: 71933-71-6
• 化学式: C₉H₇ClNO₄P
• 分子量: 259.586
• InChiKey: RMGUINKEZIIJPU-UHFFFAOYSA-N

物化性质

• 沸点：
  498.1±55.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-chloro-8-quinolyl phosphate 在 喹啉-8-磺酰氯 、 (PySe)2 、 对甲苯磺酸 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 qclpbzCtp(qcl)bzCt
  参考文献：
  名称：

  A convenient method for insertion of the 5'-terminal phosphate group in the triester approach to oligoribonucleotide synthesis

  摘要：

  DOI：

  10.1021/jo01304a042

文献信息

• Methoxyethoxymethyl group for the protection of uracil residue in oligoribonucleotide synthesis
  作者：Hiroshi Takaku、Souichi Ueda、Tsunehiko Ito

  DOI：10.1016/s0040-4039(00)87869-7

  日期：——

  Methoxyethoxymethyl group (MEM) was useful protecting group for the protection of uracil residue. This group was selectively introduced into uracil residue in good yield and removed under mild conditions.

  甲氧基乙氧基甲基（MEM）是用于保护尿嘧啶残基的有用保护基。将这一组以高收率选择性地引入尿嘧啶残基中，并在温和条件下除去。
• USE OF 3,4-DIMETHOXYBENZYL GROUP AS A PROTECTING GROUP FOR THE 2′-HYDROXYL GROUP IN THE SYNTHESIS OF OLIGORIBONUCLEOTIDES
  作者：Hiroshi Takaku、Tsunehiko Ito、Kazuaki Imai

  DOI：10.1246/cl.1986.1005

  日期：1986.6.5

  4-dimethoxybenzyl group was introduced to the 2′-hydroxyl group by the reaction of nucleosides with 3,4-dimethoxybenzyl trichloroacetimidate or 3,4-dimethoxybenzyl bromide-NaH. Further, this group can be used as a protecting group for the O6-amide group of the guanine residue. The protected nucleosides are useful starting materials for the synthesis of oligoribonucleotides. The 3,4-dimethoxybenzyl group was removed

  通过核苷与 3,4-二甲氧基苄基三氯乙酰亚胺或 3,4-二甲氧基苄基溴-NaH 的反应，将 3,4-二甲氧基苄基引入 2'-羟基。此外，该基团可用作鸟嘌呤残基的O6-酰胺基团的保护基团。受保护的核苷是合成寡核糖核苷酸的有用起始材料。通过用氧化剂处理，3,4-二甲氧基苄基从寡核糖核苷酸中迅速去除，而对糖苷键没有任何损害。
• SYNTHESIS OF OLIGORIBONUCLEOTIDES USING 4-METHOXYBENZYL GROUP AS A NEW PROTECTING GROUP OF THE 2′-HYDROXYL GROUP OF ADENOSINE
  作者：Hiroshi Takaku、Kazuo Kamaike

  DOI：10.1246/cl.1982.189

  日期：1982.2.5

  4-Methoxybenzyl group was introduced directly to the 2′-hydroxyl group from the reaction of adenosine with 4-methoxybenzyl bromide in the presence of sodium hydride. The 2′-O-(4-methoxybenzyl)adenosine can be successfully used in the synthesis of oligoribonucleotides via phosphotriester approach. The 4-methoxybenzyl group was removed rapidly from the oligoribonucleotides by triphenylmethyl fluoroborate

  4-甲氧基苄基在氢化钠存在下直接引入腺苷与4-甲氧基苄基溴反应的2'-羟基中。2'-O-(4-甲氧基苄基)腺苷可成功用于通过磷酸三酯法合成寡核糖核苷酸。4-甲氧基苄基通过氟硼酸三苯甲酯从寡核糖核苷酸中快速去除，并且完全解封闭的寡核糖核苷酸通过酶水解表征。
• SELECTIVE REMOVAL OF TERMINAL DIMETHOXYTRITYL GROUPS
  作者：Hiroshi Takaku、Kazuhiro Morita、Takashi Sumiuchi

  DOI：10.1246/cl.1983.1661

  日期：1983.11.5

  N6’N6,3′,5′-O-Protected deoxyadenosine derivatives were found to be key intermediate for synthesis of oligodeoxyribonucleotides. Treatment of protected deoxyadenosine derivatives with 3% trichloroacetic acid in nitromethane-methanol (95:5) gave the corresponding de-dimethoxytritylated deoxyadenosine derivatives without causing any damage to the glycosidic bond.

  N6'N6,3',5'-O-保护的脱氧腺苷衍生物被发现是合成寡脱氧核糖核苷酸的关键中间体。用3%三氯乙酸的硝基甲烷-甲醇(95:5)溶液处理受保护的脱氧腺苷衍生物，得到相应的脱二甲氧基三苯甲基化的脱氧腺苷衍生物，且不会对糖苷键造成任何损害。
• A Convenient Method for the Synthesis of Adenylyl-(2′–5′)-adenylyl(2′–5′)-adenosine Using 3′-<i>O</i>-Benzoyladenosine Derivatives
  作者：Hiroshi Takaku、Souichi Ueda

  DOI：10.1246/bcsj.56.1424

  日期：1983.5

  N6,3′-O-Dibenzoyladenosine was prepared by treating 2′,3′-O-(dibutylstannylene)-N6-benzoyladenosine with benzoyl chloride in methanol. The trimeric adenylyl-(2′–5′)-adenylyl-(2′–5′)-adenosine was synthesized in a good yield using N6,3′-O-dibenzoyladenosine as the starting material via the phosphotriester approach.

  N6,3'-O-二苯甲酰腺苷是通过在甲醇中用苯甲酰氯处理 2',3'-O-(二丁基亚锡)-N6-苯甲酰腺苷制备的。以 N6,3'-O-二苯甲酰腺苷为原料，通过磷酸三酯方法以良好的收率合成了三聚腺苷酸-(2'-5')-腺苷酸-(2'-5')-腺苷。