4-(trifluoromethylthio)butan-1-ol | 1001079-08-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 4-(trifluoromethylthio)butan-1-ol
• 英文别名: 4-(trifluoromethylthio)-butanol；4-(trifluoromethylsulfanyl)butan-1-ol
• CAS: 1001079-08-8
• 化学式: C₅H₉F₃OS
• 分子量: 174.187
• InChiKey: JTHKHXQDEULRTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(trifluoromethylthio)butan-1-ol 、 5‘-O-dimethoxytrityl-2’-deoxyribothymidine 3‘-O-phosphorodiamidite 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(4-trifluoromethylthiobutoxy)-(N,N-diisopropylamino)phosphinyl-2'-deoxythymidine
  参考文献：
  名称：

  Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs

  摘要：

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.10.096
• 作为产物：
  描述：

  3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环 、 4-巯基-1-丁醇 以 二氯甲烷 为溶剂， 以72%的产率得到4-(trifluoromethylthio)butan-1-ol
  参考文献：
  名称：

  Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs

  摘要：

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.10.096

文献信息

• Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs
  作者：Cristina Ausín、Jon S. Kauffman、Robert J. Duff、Shankaramma Shivaprasad、Serge L. Beaucage

  DOI：10.1016/j.tet.2009.10.096

  日期：2010.1

  Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5,12,13,18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences. Published by Elsevier Ltd.