N-methyliminodiacetyl (2-hydroxy-1-phenylpent-4-en-1-yl)boronate | 1329422-37-8

• 英文名称: N-methyliminodiacetyl (2-hydroxy-1-phenylpent-4-en-1-yl)boronate
• 英文别名: MIDA (2-hydroxy-1-phenylpent-4-en-1-yl)boronate
• CAS: 1329422-37-8；1330094-13-7
• 化学式: C₁₆H₂₀BNO₅
• 分子量: 317.149
• InChiKey: QBHFBNUZRNNTAX-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：
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• 环数：
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• 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：

  N-methyliminodiacetyl (2-hydroxy-1-phenylpent-4-en-1-yl)boronate 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S)-1-phenylpent-4-en-1,2-diol 、
  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 (2-phenyloxiran-2-yl)boronate 在 [BF₃(O(C₂H₅)2)] 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 N-methyliminodiacetyl (2-hydroxy-1-phenylpent-4-en-1-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