(R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide | 1260955-17-6

• 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: (R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide
• CAS: 1260955-17-6
• 化学式: C₁₆H₂₄BNO₃
• 分子量: 289.182
• InChiKey: QZGXWGVLLORARI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide 在 N-溴代丁二酰亚胺(NBS) 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到(R)-N-(1-(3-bromophenyl)ethyl)acetamide
  参考文献：
  名称：

  Chemoenzymatic synthesis of boron-containing chiral amines and amides

  摘要：

  The first application of lipases as catalysts to obtain optically active boron-containing amines and amides is described. We studied several reaction conditions to achieve the kinetic resolution of boron-containing amines via enantioselective acylation mediated by Candida antarctica lipase B (CAL-B). Excellent enantioselectivity (E>200) and high enantiomeric excess (up to >99%) of both the remaining amines and amides were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.011
• 作为产物：
  描述：

  3-乙酰基苯硼酸频那醇酯 在 吡啶 、 Candida boidinii formate dehydrogenase 、 L-丙氨酸 、 alanine dehydrogenase 、 磷酸吡哆醛 、 (R)-Arthrobacter sp. ω-transaminase 、 甲酸铵 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 (R)-N-(1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)acetamide
  参考文献：
  名称：

  Asymmetric reductive amination of boron-containing aryl-ketones using ω-transaminases

  摘要：

  The asymmetric reductive amination of aryl-ketones bearing various boron-functionalities (acid, ester or potassium trifluoroborates) was investigated employing enantiocomplementary omega-transaminases as catalysts. Under the optimized conditions, high conversions (up to 94%) and excellent ee's (up to >99%) were obtained providing access to both (R)- and (S)-configured amino-aryl boronates under mild reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.004