methyl 11-[N-(trifluoroacetyl)amino]undecanoate | 17634-52-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 11-[N-(trifluoroacetyl)amino]undecanoate
• 英文别名: ω-N-Trifluoracetylamino-undecansaeure-methylester
• CAS: 17634-52-5
• 化学式: C₁₄H₂₄F₃NO₃
• 分子量: 311.345
• InChiKey: CRZNRTGRYMPNDH-UHFFFAOYSA-N

物化性质

• 熔点：
  48-48.5 °C(Solvent: Hexane)
• 沸点：
  358.2±42.0 °C(predicted)
• 密度：
  1.090±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 11-[N-(trifluoroacetyl)amino]undecanoate 、 乙酸酐 、 溶剂黄146 生成 10-烯酸甲酯 、 9-十一烯酸甲酯 、 、 methyl 11-acetoxyundecanoate
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672
• 作为产物：
  描述：

  11-氨基十一酸 在 氯化亚砜 作用下， 以 乙酸乙酯 为溶剂， 反应 25.08h， 生成 methyl 11-[N-(trifluoroacetyl)amino]undecanoate
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672

文献信息

• Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Using <i>m</i>-Chloroperbenzoic Acid as a Terminal Oxidant
  作者：Kazunori Miyamoto、Yoshihisa Sei、Kentaro Yamaguchi、Masahito Ochiai

  DOI：10.1021/ja808829t

  日期：2009.2.4

  Transition metal-catalyzed oxidative cleavage of carbon-carbon multiple bonds has emerged as a powerful tool in organic synthesis. High-valent oxometals, mostly of Ru, Os, Mn, Mo, W, and Re, were used catalytically as reactive oxygen transfer agents to the multiple bonds. Reported here for the first time are the organocatalytic versions of the oxidative cleavage reactions. Our method involves use of

  过渡金属催化的碳-碳多键氧化裂解已成为有机合成中的有力工具。高价含氧金属，主要是 Ru、Os、Mn、Mo、W 和 Re，被用作催化多键的活性氧转移剂。这里首次报道了氧化裂解反应的有机催化版本。我们的方法涉及使用碘代三甲苯作为有效的有机催化剂，在无金属条件下生成活性芳基（羟基）-λ（3）-碘烷 5 和间氯过苯甲酸（m-CPBA）作为末端氧化剂。环状和无环烯烃以及脂肪族和芳香族炔烃在有机催化条件下顺利裂解为羧酸。