(1-bromo-2-oxo-1-phenylethyl)MIDA boronate | 1329422-35-6

• 英文名称: (1-bromo-2-oxo-1-phenylethyl)MIDA boronate
• 英文别名: N-methyliminodiacetyl (1-bromo-2-oxo-1-phenylethyl)boronate；MIDA (1-bromo-2-oxo-1-phenylethyl)boronate
• CAS: 1329422-35-6
• 化学式: C₁₃H₁₃BBrNO₅
• 分子量: 353.965
• InChiKey: OBKHWUQLDKKDBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  (E)-6-methyl-2-styryl-1,3,6,2-dioxazaborocane-4,8-dione 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 溴 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1-bromo-2-oxo-1-phenylethyl)MIDA 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

• Boron-Containing Enamine and Enamide Linchpins in the Synthesis of Nitrogen Heterocycles
  作者：Jeffrey D. St. Denis、Adam Zajdlik、Joanne Tan、Piera Trinchera、C. Frank Lee、Zhi He、Shinya Adachi、Andrei K. Yudin

  DOI：10.1021/ja510963k

  日期：2014.12.17

  access to the corresponding α-halo aldehydes, which undergo regioselective annulation to form borylated thiazoles. A condensation/amidation sequence converts α-boryl aldehydes into stable α-boryl enamides without concomitant C → N migration. We also show that palladium-catalyzed cyclization of α-boryl enamides leads to synthetically versatile isoindolones. These molecules can be subsequently used to access

  已经证明了 α-硼烯胺和烯酰胺在氮杂环合成中的使用。硼烯胺可以很容易地获得相应的 α-卤代醛，这些醛经过区域选择性环化形成硼化噻唑。缩合/酰胺化序列将 α-硼醛转化为稳定的 α-硼烯酰胺，而不会伴随 C → N 迁移。我们还表明，钯催化的 α-硼烯酰胺环化导致合成通用的异吲哚酮。这些分子随后可用于访问多环支架。