Lauroyloxyacetonitrile | 34097-59-1

• 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: Lauroyloxyacetonitrile
• 英文别名: cyanomethyl dodecanoate；Cyanomethyl dodecanoate
• CAS: 34097-59-1
• 化学式: C₁₄H₂₅NO₂
• 分子量: 239.358
• InChiKey: DTMXVEUQGGDWDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Lauroyloxyacetonitrile 、 蔗糖 在 正丁基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 mono-1'-O-lauroylsucrose 、 sucrose 6'-O-monolaurate 、 3-O-lauroyl sucrose 、 6-O-sucrose monolaurate 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  有机介质中蔗糖的酯交换反应：酰基迁移的研究

  摘要：

  通过HPLC，原位NMR光谱和制备方法研究了蔗糖脂肪酸酯的葡萄糖部分上的酰基在有机介质中发生分子内迁移的趋势以及一些蔗糖的酯交换反应的区域选择性。对于碱基催化的酯交换反应，通常在葡萄糖部分的次要位置上进行广泛的酰化，然后进行迁移。在一系列条件下研究了3-和6- O-酰基衍生物的稳定性，这两个异构体在热力学上比其他异构体更受青睐。结果表明，在有机碱性介质中，水的存在会催化OH-3处的酯向OH-6的迁移，而OH-6处的酯在酸性或碱性条件下显得更稳定。

  DOI：

  10.1081/car-120026466
• 作为产物：
  描述：

  月桂酸 、 溴乙腈 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 生成 Lauroyloxyacetonitrile
  参考文献：
  名称：

  Iodoacetonitrile and Bromoacetonitrile as Alkylating Reagents for the Nitrogen-Phosphorus Detector

  摘要：

  Iodoacetonitrile and bromoacetonitrile were used to enhance the sensitivity of chromatographically difficult compounds. Selective derivatization occurs with acidic hydroxyl, amino, and amide functional groups but does not occur for the alcoholic hydroxyl group. Numerous examples of model compounds (e.g,, phenols, organic acids, fatty acids, nonsteroidal antiinflammatory drugs, and xanthines) are given, The use of an element-specific detector for nitrogen-containing compounds is described, and some electron impact GC/MS data are provided for the derivatized model compounds.

  DOI：

  10.1021/ac00107a015

文献信息

• Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids
  作者：Hongxiang Wang、Ying Shao、Hao Zheng、Hanghang Wang、Jiang Cheng、Xiaobing Wan

  DOI：10.1002/chem.201502733

  日期：2015.12.7

  Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α‐aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination–decarboxylation

  使用氰基乙酸作为掩蔽的亲电试剂，开发了一种新的胺和羧酸的氰基甲基化反应，以高收率和出色的功能耐受性生产了多种α-氨基腈和氰基甲基酯。该方案具有操作简单，试剂便宜和底物范围广的特点。在此转化过程中，氰基乙酸的碘化-脱羧反应原位生成了碘乙腈。
• Byers, Jeffrey H.; Baran, Robert C.; Craig, Molly E., Organic Preparations and Procedures International, 1991, vol. 23, # 3, p. 373 - 374
  作者：Byers, Jeffrey H.、Baran, Robert C.、Craig, Molly E.、Jackman, John T.

  DOI：——

  日期：——
• Iodoacetonitrile and Bromoacetonitrile as Alkylating Reagents for the Nitrogen-Phosphorus Detector
  作者：Ho-Sang. Shin、Seungki. Kim、Seung-Woon. Myung、Jong-Sei. Park

  DOI：10.1021/ac00107a015

  日期：1995.6.1

  Iodoacetonitrile and bromoacetonitrile were used to enhance the sensitivity of chromatographically difficult compounds. Selective derivatization occurs with acidic hydroxyl, amino, and amide functional groups but does not occur for the alcoholic hydroxyl group. Numerous examples of model compounds (e.g,, phenols, organic acids, fatty acids, nonsteroidal antiinflammatory drugs, and xanthines) are given, The use of an element-specific detector for nitrogen-containing compounds is described, and some electron impact GC/MS data are provided for the derivatized model compounds.
• Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations
  作者：Valérie Molinier、Krzysztof Wisniewski、Alain Bouchu、Juliette Fitremann、Yves Queneau

  DOI：10.1081/car-120026466

  日期：2003.12.31

  of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3‐ and 6‐O‐acyl derivatives

  通过HPLC，原位NMR光谱和制备方法研究了蔗糖脂肪酸酯的葡萄糖部分上的酰基在有机介质中发生分子内迁移的趋势以及一些蔗糖的酯交换反应的区域选择性。对于碱基催化的酯交换反应，通常在葡萄糖部分的次要位置上进行广泛的酰化，然后进行迁移。在一系列条件下研究了3-和6- O-酰基衍生物的稳定性，这两个异构体在热力学上比其他异构体更受青睐。结果表明，在有机碱性介质中，水的存在会催化OH-3处的酯向OH-6的迁移，而OH-6处的酯在酸性或碱性条件下显得更稳定。