(S)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid | 1029439-42-6

• 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: (S)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid
• 英文别名: [4-[[(1S)-1-phenylethyl]carbamoyl]phenyl]boronic acid
• CAS: 1029439-42-6
• 化学式: C₁₅H₁₆BNO₃
• 分子量: 269.108
• InChiKey: SKIMDRHUSPPKCV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid 、 5-溴-2-羟基-1,3-苯二羧醛 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以16%的产率得到(S)-3',5'-diformyl-4'-hydroxy-N-(1-phenylethyl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  ‘Double chiral’ new members of calixsalen family

  摘要：

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.021
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid
  参考文献：
  名称：

  ‘Double chiral’ new members of calixsalen family

  摘要：

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.021

文献信息

• ‘Double chiral’ new members of calixsalen family
  作者：Małgorzata Petryk、Agnieszka Janiak、Marcin Kwit

  DOI：10.1016/j.tetasy.2017.08.021

  日期：2017.10

  Synthesis and X-ray diffraction studies on the first examples of 'double chiral' calixsalens are presented. In these molecules, one can clearly distinguish two chiral zones. The first one is made by the macrocycle base, whereas the second chiral zone is set up of the additional chirality elements in the tail of the molecule. The 'double chiral' calixsalens are formed through cyclocondensation between chiral vicinal diamine of trans-1,2-diaminocyclohexane type and chiral C-5 substituted 2-hydroxyisophthalaldehyde derivatives. The absolute configuration of the dialdehyde did not affect the yield of the macrocyclization reaction. The presence of secondary amides in the tail part of the macrocycle leads to formation of hydrogen bonding network in the solid state, while sterical hindrance preserve interdigitation, thus, 'double chiral' calixsalens do not form aggregates typical for other calixsalens. (C) 2017 Elsevier Ltd. All rights reserved.