1-(acetylthio)-5-<(tert-butyldimethylsilyl)oxy>pentane | 145457-72-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(acetylthio)-5-<(tert-butyldimethylsilyl)oxy>pentane
• 英文别名: S-[5-[tert-butyl(dimethyl)silyl]oxypentyl] ethanethioate
• CAS: 145457-72-3
• 化学式: C₁₃H₂₈O₂SSi
• 分子量: 276.516
• InChiKey: MRBZNLIKXWACNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(acetylthio)-5-<(tert-butyldimethylsilyl)oxy>pentane 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668

  摘要：

  Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.

  DOI：

  10.1016/0968-0896(95)00180-8
• 作为产物：
  描述：

  5-氯-1-戊醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(acetylthio)-5-<(tert-butyldimethylsilyl)oxy>pentane
  参考文献：
  名称：

  Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668

  摘要：

  Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.

  DOI：

  10.1016/0968-0896(95)00180-8

文献信息

• Calcium Entry Blockers and Activators: Conformational and Structural Determinants of Dihydropyrimidine Calcium Channel Modulators
  作者：George C. Rovnyak、S. David Kimball、Barbara Beyer、Gabriella Cucinotta、John D. DiMarco、Jack Gougoutas、Anders Hedberg、Mary Malley、James P. McCarthy

  DOI：10.1021/jm00001a017

  日期：1995.1

  Dihydropyrimidines 4, 6, and 15, uniquely designed to unambiguously establish structural and conformational determinants for DHP receptor occupation and for modulation of calcium channel function, were prepared and examined for calcium channel modulation. Our results confirm and firmly establish a preference for syn-orientation of an unsymmetrically substituted aryl moiety at the DHP receptor (15d vs 15e). We propose a normal vs capsized DHP boat model to explain structural and conformational requirements for modulation of calcium channel function that requires an obligatory left-hand side alkoxy cis-carbonyl interaction for maximal DHP receptor affinity, the effect on channel function being determined by orientation of the 4-aryl group. Enantiomers having an up-oriented pseudoaxial aryl group (normal DHP boat) will elicit calcium antagonist activity, whereas enantiomers having a down-oriented pseudoaxial aryl group (capsized DHP boat) will elicit calcium agonist activity. Single enantiomers of macrocyclic lactone 15b demonstrate opposite channel activity. Antagonist activity resides in enantiomer 15b-A (S-configuration, left-hand side alkoxy cis-carbonyl with up-oriented pseudoaxial aryl group and normal DHP boat), whereas agonist activity resides in enantiomer 15b-B (R-configuration, left-hand side alkoxy cis-carbonyl with down-oriented pseudoaxial aryl group and capsized DHP boat). Moreover, this model is consistent with and provides a rational explanation of previous literature in this area, most notably the observation of chiral inversion and potency diminution upon replacement of ester by hydrogen in the Bay K 8644 series.
• Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668
  作者：Hiroshi Miyauchi、Koichi Kozuki、Tomoharu Tanio、Naohito Ohashi

  DOI：10.1016/0968-0896(95)00180-8

  日期：1996.2

  Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.