2-N-acryloylaminophenylboronic acid pinacol ester | 434898-97-2

• 英文名称: 2-N-acryloylaminophenylboronic acid pinacol ester
• CAS: 434898-97-2
• 化学式: C₁₅H₂₀BNO₃
• 分子量: 273.14
• InChiKey: JBXFOLPTNPLREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
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• 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：

  2-N-acryloylaminophenylboronic acid pinacol ester 、 环戊二烯 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 生成 (1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide 、 (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide
  参考文献：
  名称：

  Design of chiral boronate-substituted acrylanilides.

  摘要：

  The [4 + 2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9-13 provided a small level of remote 1,8-stereoinduction transmitted through a putative tetrahedral stereogenic boronate complex. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00400-5
• 作为产物：
  描述：

  丙烯酰氯 、 2-氨基苯硼酸频哪醇酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到2-N-acryloylaminophenylboronic acid pinacol ester
  参考文献：
  名称：

  Design of chiral boronate-substituted acrylanilides.

  摘要：

  The [4 + 2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9-13 provided a small level of remote 1,8-stereoinduction transmitted through a putative tetrahedral stereogenic boronate complex. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00400-5