MIDA (2-phenyloxiran-2-yl)boronate | 1329422-31-2

• 英文名称: MIDA (2-phenyloxiran-2-yl)boronate
• 英文别名: N-methyliminodiacetyl (2-phenyloxiran-2-yl)boronate
• CAS: 1329422-31-2
• 化学式: C₁₃H₁₄BNO₅
• 分子量: 275.069
• InChiKey: XRBOCUMQFXWWBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  MIDA (2-phenyloxiran-2-yl)boronate 在 [BF₃(O(C₂H₅)2)] 、 NaH₂PO₄ 、 cyclohexene 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 2-(N-methyliminodiacetylboryl)-2-phenylacetic acid
  参考文献：
  名称：

  Amphoteric α-Boryl Aldehydes

  摘要：

  A new class of stable molecules, alpha-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from alpha-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of alpha-boryl aldehydes in chemical synthesis.

  DOI：

  10.1021/ja205910d
• 作为产物：
  描述：

  MIDA alkenyl-2-boronate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到MIDA (2-phenyloxiran-2-yl)boronate
  参考文献：
  名称：

  Amphoteric α-Boryl Aldehydes

  摘要：

  A new class of stable molecules, alpha-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from alpha-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of alpha-boryl aldehydes in chemical synthesis.

  DOI：

  10.1021/ja205910d

文献信息

• An Exploration of Regioselectivity During Formation of Aminoboronates from Epoxides
  作者：Andrei K. Yudin、Alina Trofimova、Chelsey Brien、Joanne Tan、Vincent Trudel

  DOI：10.1055/s-0043-1763674

  日期：2024.5

  α-Aminoboronic acids and their derivatives are important synthetic targets. Our research interest has been focused on the synthesis and applications of MIDA (N-methyliminodiacetic acid) protected aminoboronates. Herein we report syntheses of regioisomeric β-borylated azidoalcohols. The geminal azidoboronate represents a rare example of an α-azidoalcohol and is produced through trapping of oxonium ions

  α-氨基硼酸及其衍生物是重要的合成目标。我们的研究兴趣集中在MIDA（N-甲基亚氨基二乙酸）保护的氨基硼酸酯的合成和应用。在此，我们报道了区域异构β-硼化叠氮醇的合成。偕叠氮硼酸酯代表了 α-叠氮醇的罕见例子，是通过捕获在 α-硼醛重排过程中产生的氧鎓离子而产生的。邻位叠氮硼酸酯可以从α-溴乙酰基MIDA硼酸酯获得，并且能够通过施陶丁格反应制备氮丙啶MIDA硼酸酯。