2-(2-methylthioethoxy)ethanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-methylthioethoxy)ethanol
• 英文别名: (2-(methylthio)ethoxy)ethanol；2-(2-methylsulfanyl-ethoxy)-ethanol；2-(2-Methylsulfanylethoxy)ethanol
• 化学式: C₅H₁₂O₂S
• 分子量: 136.215
• InChiKey: BBRVKBQHXLIOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 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：

  2-(2-methylthioethoxy)ethanol 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以66%的产率得到[2-(2-(methylthio)ethoxy)]ethyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of O-1–O-6 Substituted Positional Isomers of d-Glucose–Thioether Ligands and Their Ruthenium Polypyridyl Conjugates

  摘要：

  A library of positional isomers of n-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.

  DOI：

  10.1021/acs.joc.8b01342
• 作为产物：
  描述：

  CH3SCH2CH2OCH2COOEt 在 lithium aluminium tetrahydride 、 水 、 potassium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以2.1 g的产率得到2-(2-methylthioethoxy)ethanol
  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

• The Influence of Heteroatom-substituted Methyl Groups and of Vinyl Groups (CR₂=CR—) Attached to C-2 of 1,3-Dioxolanes on the Ease and Direction of Hydrogenolysis of the 1,3-Dioxolanes by AlH₂Cl, AlH₃, or LiAlH₄
  作者：H. A. Davis、R. K. Brown

  DOI：10.1139/v71-422

  日期：1971.8.1

  AlH2Cl or AlH3 in diethyl ether at room temperature reduces 2-vinyl- or 2-[alkyl (or aryl) substituted vinyl]-1,3-dioxolanes to only the β,γ-unsaturated alkyl β-hydroxyethyl ether, the product expected from hydride ion addition to C-2 of the 1,3-dioxolane. The ease of hydrogenolysis increases with increasing alkyl (or aryl) substitution on the 2-vinyl group.LiAlH4 in diethyl ether at room temperature, or

  2-甲基-1,3-二氧戊环的甲基上的杂原子取代基阻碍了 2-取代的 1,3-二氧戊环的醚溶液的 AlH2Cl 的氢解速率。杂原子在降低氢解容易度方面的有效性是 H < S < O < Br < NR2。这种延迟被认为是由于杂原子的电负性和/或一些 AlH2Cl 与杂原子的配位引起的过渡态不稳定导致中间氧碳离子。AlH2Cl 或 AlH3 在室温下乙醚中将 2-乙烯基-或 2-[烷基（或芳基）取代的乙烯基]-1,3-二氧戊环还原为仅 β,γ-不饱和烷基 β-羟乙基醚，预期产物是氢阴离子加成到 C-2 1,3-二氧戊环。
• Synthesis of <i>O</i>-1–<i>O</i>-6 Substituted Positional Isomers of <scp>d</scp>-Glucose–Thioether Ligands and Their Ruthenium Polypyridyl Conjugates
  作者：Lucien N. Lameijer、Julien le Roy、Stefan van der Vorm、Sylvestre Bonnet

  DOI：10.1021/acs.joc.8b01342

  日期：2018.11.2

  A library of positional isomers of n-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.
• 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.