3-decylsulfanyl-propane-1,2-diol | 24724-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-decylsulfanyl-propane-1,2-diol
• 英文别名: 2.3-Dihydroxypropyl-decansulfid；3-Decylthio-1,2-propanediol；3-decylsulfanylpropane-1,2-diol
• CAS: 24724-30-9
• 化学式: C₁₃H₂₈O₂S
• 分子量: 248.43
• InChiKey: ZCTCMSMNMSTPIV-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  384.7±22.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-decylsulfanyl-propane-1,2-diol 在 吡啶 、 咪唑 、 四丁基氟化铵 、 水 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 55.0h， 生成 Hexadecanoic acid 1-decylsulfanylmethyl-2-phosphonooxy-ethyl ester
  参考文献：
  名称：

  Nucleoside conjugates. 13. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of thioether lipids with improved water solubility

  摘要：

  A series of ara-CDP-rac-1-S-alkyl-2-0-acyl-1-thioglycerols (3-12), analogues of highly active Cytoros2 (1), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. The conjugates with sn-1 alkyl (C14) and the sn-2 fatty acyl (>C16) were sparingly soluble. The latter formed micelles upon sonication. Conjugate 7 containing the sn-1 tetradecyl and the sn-2 palmitoyl (C16) groups formed micelles by both sonication and shaking. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 20 times greater than that of ara-C. The water-insoluble showed a more than 40 times increase. A single dose of the micelle-forming conjugates 7 and 10 produced a significant increase in life span (ILS >421 %) with 50 % long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of previous micelle-forming conjugate 1 (Cytoros). In contrast, the water-soluble conjugates at single doses were less effective (ILS 81-386% with 0-33% long-term survivors). However, three divided doses of the water-soluble conjugates were found to be as effective as a single dose of micellar solution of the water-insoluble. The results indicate that conjugate 7 and most of the water-soluble derivatives warrant further investigation.

  DOI：

  10.1021/jm00064a012
• 作为产物：
  描述：

  1-硫代甘油 、 癸基溴 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 3-decylsulfanyl-propane-1,2-diol
  参考文献：
  名称：

  Doren, Henk A. van; Geest, Ralph van der; Kellogg, Richard M., Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 3, p. 197 - 203

  摘要：

  DOI：

文献信息

• Doren, Henk A. van; Geest, Ralph van der; Kellogg, Richard M., Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 3, p. 197 - 203
  作者：Doren, Henk A. van、Geest, Ralph van der、Kellogg, Richard M.、Wynberg, Hans

  DOI：——

  日期：——
• Functionally substituted sulfur-containing compounds. 9. Reactions of 2-[(organylthio)methyl]oxiranes with acetic anhydride and acetyl chloride
  作者：V. E. Kalugin、V. P. Litvinov

  DOI：10.1007/bf00961238

  日期：1991.7

  Reaction of 2-[(organylthio)methyl]oxiranes with acetic anhydride gives a mixture of 3-(organylthio)-1,2-diacetoxypropane and 2-(organylthio)-1,3-diacetoxypropane, and with acetyl chloride a mixture of 2-chloro-3-(organylthio)-1-acetoxypropane and 3-chloro-2-(organylthio)-1-acetoxypropane. In both cases, the ratio of the isomers depends on the nature of the organylthio group and on the nature of the electrophile.
• Notes. Synthesis of the Sulfur Analogs of Batyl and Chimyl Alcohols
  作者：D Lawson、Horace Getz、Donald Miller

  DOI：10.1021/jo01061a619

  日期：1961.2
• KALUGIN, V. E.;LITVINOV, V. P., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1574-1578
  作者：KALUGIN, V. E.、LITVINOV, V. P.

  DOI：——

  日期：——
• Nucleoside conjugates. 13. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of thioether lipids with improved water solubility
  作者：Chung Il Hong、Alexander Nechaev、Alan J. Kirisits、Rakesh Vig、Charles R. West

  DOI：10.1021/jm00064a012

  日期：1993.6

  A series of ara-CDP-rac-1-S-alkyl-2-0-acyl-1-thioglycerols (3-12), analogues of highly active Cytoros2 (1), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. The conjugates with sn-1 alkyl (C14) and the sn-2 fatty acyl (>C16) were sparingly soluble. The latter formed micelles upon sonication. Conjugate 7 containing the sn-1 tetradecyl and the sn-2 palmitoyl (C16) groups formed micelles by both sonication and shaking. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 20 times greater than that of ara-C. The water-insoluble showed a more than 40 times increase. A single dose of the micelle-forming conjugates 7 and 10 produced a significant increase in life span (ILS >421 %) with 50 % long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of previous micelle-forming conjugate 1 (Cytoros). In contrast, the water-soluble conjugates at single doses were less effective (ILS 81-386% with 0-33% long-term survivors). However, three divided doses of the water-soluble conjugates were found to be as effective as a single dose of micellar solution of the water-insoluble. The results indicate that conjugate 7 and most of the water-soluble derivatives warrant further investigation.