S-(3-chloropropyl)-N-mercaptophthalimide | 144527-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: S-(3-chloropropyl)-N-mercaptophthalimide
• 英文别名: 2-[(3-Chloropropyl)sulfanyl]-1H-isoindole-1,3(2H)-dione；2-(3-chloropropylsulfanyl)isoindole-1,3-dione
• CAS: 144527-79-7
• 化学式: C₁₁H₁₀ClNO₂S
• 分子量: 255.725
• InChiKey: YERHZQJOKOHLTN-UHFFFAOYSA-N

物化性质

• 沸点：
  410.0±47.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(3-chloropropyl)-N-mercaptophthalimide 、 2'-deoxy-4-thiouridine 在 potassium phosphate buffer 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80%的产率得到S-((3-chloropropyl)thio)-4-thio-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and Postsynthetic Modification of Oligodeoxynucleotides Containing 4-Thio-2'-deoxyuridine (ds4U)

  摘要：

  Protected phosphoramidite 2 was used to incorporate synthetically the non-natural nucleoside 4-thio-2'-deoxyuridine (d(S4)U) at a specified position within oligonucleotide 3. Following DNA synthesis, the thiocarbonyl group of the 4-thio-2'-deoxyuridine of 3 was modified chemoselectively and quantitatively with thiol-specific reagents to afford oligonucleotides 14, 15, and 16 by S-alkylation or mixed disulfide formation. This protocol represents a divergent postsynthetic modification method for incorporating a wide range of functional groups at any base position within a DNA strand, starting from a single oligonucleotide intermediate.

  DOI：

  10.1021/ja00105a002

文献信息

• Synthesis of a 4-thio-2'-deoxyuridine containing oligonucleotide. Development of the thiocarbonyl group as a linker element.
  作者：Robert S. Coleman、James M. Siedlecki

  DOI：10.1021/ja00049a089

  日期：1992.11
• Synthesis and Postsynthetic Modification of Oligodeoxynucleotides Containing 4-Thio-2'-deoxyuridine (ds4U)
  作者：Robert S. Coleman、Edward A. Kesicki

  DOI：10.1021/ja00105a002

  日期：1994.12

  Protected phosphoramidite 2 was used to incorporate synthetically the non-natural nucleoside 4-thio-2'-deoxyuridine (d(S4)U) at a specified position within oligonucleotide 3. Following DNA synthesis, the thiocarbonyl group of the 4-thio-2'-deoxyuridine of 3 was modified chemoselectively and quantitatively with thiol-specific reagents to afford oligonucleotides 14, 15, and 16 by S-alkylation or mixed disulfide formation. This protocol represents a divergent postsynthetic modification method for incorporating a wide range of functional groups at any base position within a DNA strand, starting from a single oligonucleotide intermediate.