(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine | 1260955-12-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine
• 英文别名: (1S)-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethan-1-amine；(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanamine
• CAS: 1260955-12-1
• 化学式: C₁₄H₂₂BNO₂
• 分子量: 247.145
• InChiKey: WOWCIGGGXSUZIG-JTQLQIEISA-N

物化性质

• 沸点：
  347.9±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine 、 乙酸酐 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (S)-N-(1-(4-hydroxyphenyl)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
• 作为产物：
  描述：

  钾(4-乙酰基苯基)(三氟)硼酸酯(1-) 在 Candida boidinii formate dehydrogenase 、 L-丙氨酸 、 alanine dehydrogenase 、 磷酸吡哆醛 、 Chromobacterium violaceum ω-transaminase 、 甲酸铵 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 silica gel 作用下， 以 aq. phosphate buffer 为溶剂， 反应 26.0h， 生成 (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine
  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

文献信息

• Chemoenzymatic synthesis of boron-containing chiral amines and amides
  作者：Leandro H. Andrade、Thiago Barcellos、Carolina G. Santiago

  DOI：10.1016/j.tetasy.2010.09.011

  日期：2010.10

  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.
• Asymmetric reductive amination of boron-containing aryl-ketones using ω-transaminases
  作者：Joel S. Reis、Robert C. Simon、Wolfgang Kroutil、Leandro H. Andrade

  DOI：10.1016/j.tetasy.2013.10.004

  日期：2013.12

  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.