3-(methylthiomethoxy)propan-1-ol | 1206537-50-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 3-(methylthiomethoxy)propan-1-ol
• 英文别名: 3-(Methylsulfanylmethoxy)propan-1-ol；3-(methylsulfanylmethoxy)propan-1-ol
• CAS: 1206537-50-9
• 化学式: C₅H₁₂O₂S
• 分子量: 136.215
• InChiKey: ZNDYEEQHMDAYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylthiomethoxy)propan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以62%的产率得到3-(methylthiomethoxy)propanal
  参考文献：
  名称：

  O-Substituted Alkyl Aldehydes for Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Utility of Methylthiomethyl Ethers

  摘要：

  Combining a-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]CIO(4) results in efficient intermolecular alkyne hydroacylation to deliver alpha-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

  DOI：

  10.1021/ol1030662
• 作为产物：
  描述：

  乙酸甲硫甲酯 、 1,3-丙二醇 在 Amberlyst₁₅ 作用下， 反应 43.0h， 以40%的产率得到3-(methylthiomethoxy)propan-1-ol
  参考文献：
  名称：

  O-Substituted Alkyl Aldehydes for Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Utility of Methylthiomethyl Ethers

  摘要：

  Combining a-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]CIO(4) results in efficient intermolecular alkyne hydroacylation to deliver alpha-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.

  DOI：

  10.1021/ol1030662

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.
• <i>O</i>-Substituted Alkyl Aldehydes for Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Utility of Methylthiomethyl Ethers
  作者：Scott R. Parsons、Joel F. Hooper、Michael C. Willis

  DOI：10.1021/ol1030662

  日期：2011.3.4

  Combining a-methylthiomethyl (MTM) ether substituted aldehydes and 1-alkynes in the presence of [Rh(dppe)]CIO(4) results in efficient intermolecular alkyne hydroacylation to deliver alpha-O-MTM-substituted enone products. The product MTM ethers can be converted to the free hydroxyl group either in situ, by the addition of water to the completed reaction, or in a separate operation, by the action of silver nitrate.