(4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid | 1551543-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid
• 英文别名: (4R,5R)-2,2-dimethyl-5-[(1E,3R)-3-methylhexa-1,5-dienyl]-1,3-dioxolane-4-carboxylic acid
• CAS: 1551543-35-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: YATBCOCCZZLEQU-QMVIJHPZSA-N

物化性质

• 沸点：
  350.7±42.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 40.5h， 生成 (3aR,6S,7S,11R,13aR,E)-6-(3-(hydroxymethyl)phenyl)-2,2,7,11-tetramethyl-6,7,8,9,10,11-hexahydro-3aH-[1,3]dioxolo[4,5-c][1]oxacyclododecin-4(13aH)-one
  参考文献：
  名称：

  Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms

  摘要：

  The oral microbiome is a dynamic environment inhabited by both commensals and pathogens. Among these is Streptococcus mutans, the causative agent of dental caries, the most prevalent childhood disease. Carolacton has remarkably specific activity against S. mutans, causing acid-mediated cell death during biofilm formation; however, its complex structure limits its utility. Herein, we report the diverted total synthesis and biological evaluation of a rationally designed library of simplified analogs that unveiled three unique biofilm phenotypes further validating the role of natural product synthesis in the discovery of new biological phenomena.

  DOI：

  10.1021/jacs.7b03879
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 4-二甲氨基吡啶 、 sodium periodate 、 草酰氯 、 copper(l) cyanide 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 126.0h， 生成 (4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid
  参考文献：
  名称：

  Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms

  摘要：

  The oral microbiome is a dynamic environment inhabited by both commensals and pathogens. Among these is Streptococcus mutans, the causative agent of dental caries, the most prevalent childhood disease. Carolacton has remarkably specific activity against S. mutans, causing acid-mediated cell death during biofilm formation; however, its complex structure limits its utility. Herein, we report the diverted total synthesis and biological evaluation of a rationally designed library of simplified analogs that unveiled three unique biofilm phenotypes further validating the role of natural product synthesis in the discovery of new biological phenomena.

  DOI：

  10.1021/jacs.7b03879

文献信息

• A Concise Synthesis of Carolacton
  作者：Michal S. Hallside、Richard S. Brzozowski、William M. Wuest、Andrew J. Phillips

  DOI：10.1021/ol500004k

  日期：2014.2.21

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.