N-[(3S,5S)-5-(hydroxymethyl)-2-oxooxolan-3-yl]hexanamide | 428510-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(3S,5S)-5-(hydroxymethyl)-2-oxooxolan-3-yl]hexanamide
• CAS: 428510-06-9
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: LWSYKACWODZMSD-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异氰酸乙酯 、 N-[(3S,5S)-5-(hydroxymethyl)-2-oxooxolan-3-yl]hexanamide 在 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到[(2S,4S)-4-(hexanoylamino)-5-oxooxolan-2-yl]methyl N-ethylcarbamate
  参考文献：
  名称：

  Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

  摘要：

  The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00756-9
• 作为产物：
  描述：

  methyl (2S)-2-benzyloxycarboxamido-4-pentenoate 在 palladium on activated charcoal potassium osmate(VI) 、 N-甲基吲哚酮 、 氢气 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 N-[(3S,5S)-5-(hydroxymethyl)-2-oxooxolan-3-yl]hexanamide
  参考文献：
  名称：

  Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

  摘要：

  The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00756-9

文献信息

• Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers
  作者：J.A Olsen、R Severinsen、T.B Rasmussen、M Hentzer、M Givskov、J Nielsen

  DOI：10.1016/s0960-894x(01)00756-9

  日期：2002.2

  The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system. (C) 2002 Elsevier Science Ltd. All rights reserved.