2-nitro-6-methylphenylboronic acid neopentylglycol ester | 616227-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-nitro-6-methylphenylboronic acid neopentylglycol ester
• 英文别名: 5,5-dimethyl-2-(2-methyl-6-nitrophenyl)-1,3,2-dioxaborinane
• CAS: 616227-09-9
• 化学式: C₁₂H₁₆BNO₄
• 分子量: 249.074
• InChiKey: HHEHFBWYJFJGQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-nitro-6-methylphenylboronic acid neopentylglycol ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 53.5h， 生成
  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：

  2-溴-3-硝基甲苯 、 联硼酸新戊二醇酯 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 1,1'-双(二苯基膦)二茂铁 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以60%的产率得到2-nitro-6-methylphenylboronic acid neopentylglycol 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