(2-Propyl-[1,3]dioxolan-2-yl)-methanesulfonic acid ethyl ester | 797059-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-Propyl-[1,3]dioxolan-2-yl)-methanesulfonic acid ethyl ester
• 英文别名: Ethyl (2-propyl-1,3-dioxolan-2-yl)methanesulfonate
• CAS: 797059-88-2
• 化学式: C₉H₁₈O₅S
• 分子量: 238.305
• InChiKey: MIOOXNWRXIDALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Propyl-[1,3]dioxolan-2-yl)-methanesulfonic acid ethyl ester 在 磺酰氯 、 三苯基膦 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 66.0h， 生成 2-Oxo-pentane-1-sulfonic acid (2-oxo-tetrahydro-furan-3-yl)-amide
  参考文献：
  名称：

  N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing

  摘要：

  A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.088
• 作为产物：
  描述：

  乙二醇 、 2-Oxo-pentane-1-sulfonic acid ethyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 (2-Propyl-[1,3]dioxolan-2-yl)-methanesulfonic acid ethyl ester
  参考文献：
  名称：

  N-Sulfonyl homoserine lactones as antagonists of bacterial quorum sensing

  摘要：

  A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.088