phenyl 2-iodopropionate | 251346-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 2-iodopropionate
• 英文别名: Phenyl 2-iodopropanoate
• CAS: 251346-05-1
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: OLPHWZAQGADCTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl 2-iodopropionate 在 三乙基硼 、 氧气 、 甲醇 、 二甲基硫 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.25h， 以82%的产率得到苯酚-乳酸
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n
• 作为产物：
  描述：

  苯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 potassium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.5h， 生成 phenyl 2-iodopropionate
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n

文献信息

• Process for obtaining ionic amino acid esters
  申请人：INSTITUTO MEXICANO DEL PETRÓLEO

  公开号：US10384247B2

  公开（公告）日：2019-08-20

  Embodiments of the present invention provide for efficient methods and processes for preparing ionic amino acid esters from a specific synthesis route. The disclosed embodiments consist of a single reaction step: reacting a natural or synthetic unprotected amino acid with an aliphatic, branched or aromatic fatty alcohol of even or odd number of carbon atoms from 6 to 20 with or without unsaturation(s), in stoichiometric amounts, in the presence of an organic acid (HX) like carboxylate, mesylate, tosylate or sulfonate, employed as catalyst and under conventional heating (CC) of 1 to 3 hours at a temperature in the range of approximately 60 to 150° C. and pressure the range of approximately 0 to approximately 250 psi; the product obtained is cooled and recrystallized from ethanol.

  本发明的实施例提供了从特定合成途径制备离子氨基酸酯的高效方法和工艺。所公开的实施方案包括一个反应步骤：在有机酸（HX）如羧酸盐、甲磺酸盐、对磺酸盐作为催化剂的存在下，在常规加热（CC）条件下，在温度约为 60 至 150 摄氏度、压力约为 0 至约 250 磅/平方英寸的范围内，使天然或合成的未受保护氨基酸与偶数或奇数碳原子数（6 至 20）的脂肪醇、支链脂肪醇或芳香脂肪醇反应，反应量为等比数列。将得到的产品冷却并从乙醇中重结晶。