(R)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid | 1029439-43-7

• 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)-(4-((1-phenylethyl)carbamoyl)phenyl)boronic acid
• 英文别名: [4-[[(1R)-1-phenylethyl]carbamoyl]phenyl]boronic acid
• CAS: 1029439-43-7
• 化学式: C₁₅H₁₆BNO₃
• 分子量: 269.108
• InChiKey: SKIMDRHUSPPKCV-LLVKDONJSA-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：

  (R)-(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22%的产率得到(R)-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：

  4-溴苯甲酸 在 正丁基锂 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (R)-(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

• [EN] CHIRAL ORGANIC SANDWICH AND MULTI-LAYER CHIRALITY OF MOLECULES AND ACHIRAL DERIVATIVES<br/>[FR] SANDWICH ORGANIQUE CHIRAL ET CHIRALITÉ MULTICOUCHES DE MOLÉCULES ET DE DÉRIVÉS ACHIRAUX
  申请人：UNIV TEXAS TECH SYSTEM

  公开号：WO2020123613A1

  公开（公告）日：2020-06-18

  The present invention includes a multi-layer 3D material, a method of making, and a catalyst comprising: a first, a second, and a third layer, wherein each of the layers are arranged in a nearly parallel fashion with chirality along a center plane.

  本发明涵盖了一种多层3D材料，一种制备方法，以及包括：第一层、第二层和第三层的催化剂，其中每一层都以沿中心平面的手性近似平行方式排列。
• From Center-to-Multilayer Chirality: Asymmetric Synthesis of Multilayer Targets with Electron-Rich Bridges
  作者：Yao Tang、Guanzhao Wu、Shengzhou Jin、Yangxue Liu、Liulei Ma、Sai Zhang、Hossein Rouh、Ahmed I. M. Ali、Jia-Yin Wang、Ting Xu、Daniel Unruh、Kazimierz Surowiec、Guigen Li

  DOI：10.1021/acs.joc.2c00234

  日期：2022.5.6

  Asymmetric synthesis of new atropisomerically multilayered chiral targets has been achieved by taking advantage of the strategy of center-to-multilayer chirality and double Suzuki–Miyaura couplings. Diastereomers were readily separated via flash column chromatography and well characterized. Absolute configuration assignment was determined by X-ray structural analysis. Five enantiomerically pure isomers

  通过利用中心到多层手性和双 Suzuki-Miyaura 耦合的策略，已经实现了新的阻转异构多层手性目标的不对称合成。非对映异构体很容易通过快速柱色谱分离并很好地表征。绝对配置分配由 X 射线结构分析确定。五种具有多层手性的纯对映异构体是利用涉及富电子芳香连接的锚来组装的。从市售起始材料经过 11 个步骤，最终获得 0.69% 的带有羟基连接的目标物的总产率。