2-[(R)-1-phenylpropyl]benzo[d]oxazole | 1417544-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-[(R)-1-phenylpropyl]benzo[d]oxazole
• 英文别名: 2-(1-phenylpropyl)benzo[d]oxazole；2-[(1R)-1-phenylpropyl]-1,3-benzoxazole
• CAS: 1417544-45-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: CRYRHVAWOGFABH-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2R)-N-(2-hydroxyphenyl)-2-phenylbutanamide 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 2-[(R)-1-phenylpropyl]benzo[d]oxazole
  参考文献：
  名称：

  A microwave assisted synthesis of benzoxazoles from carboxylic acids

  摘要：

  A series of various poly-substituted benzoxazoles were synthesized starting from readily available carboxylic acids. The method is based on TCT (cyanuric chloride)/microwave acid activation and it is characterized by mild conditions, allowing for a wide range of starting materials and functionalization of final products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.084

文献信息

• Light‐Promoted Copper‐Catalyzed Enantioselective Alkylation of Azoles
  作者：Chen Li、Bin Chen、Xiaodong Ma、Xueling Mo、Guozhu Zhang

  DOI：10.1002/anie.202009323

  日期：2021.1.25

  A catalytic asymmetric alkylation of azoles with secondary 1‐arylalkyl bromides through direct C−H functionalization is reported. Under blue‐light photoexcitation, a copper(I)/carbazole‐based bisoxazoline (CbzBox) catalytic system exhibits good reactivity and high stereoselectivity, thus offering an efficient strategy for the construction of chiral alkyl azoles. These reactions proceed at low temperature

  据报道，通过直接的C H官能化，仲仲1-芳基烷基溴催化了唑类的催化不对称烷基化。在蓝光光激发下，基于铜（I）/咔唑的双恶唑啉（CbzBox）催化体系表现出良好的反应性和高的立体选择性，从而为构建手性烷基唑提供了有效的策略。这些反应在低温下进行，并与各种唑类相容。
• Nickel-Catalyzed Intermolecular Enantioselective Heteroaromatic C–H Alkylation
  作者：Mo Chen、John Montgomery

  DOI：10.1021/acscatal.2c03228

  日期：2022.9.16

  Regio- and enantioselective functionalization of heteroarene C–H bonds in the absence of directing groups is a long-standing challenge in the field of C–H activation. Herein, we present an approach involving nickel-catalyzed intermolecular enantioselective C–H alkylation of heteroarenes. The process can be carried out under mild conditions using nickel(0) catalysts with N-heterocyclic carbene (NHC)

  在没有导向基团的情况下，杂芳烃 C-H 键的区域和对映选择性功能化是 C-H 活化领域的长期挑战。在此，我们提出了一种涉及镍催化的杂芳烃分子间对映选择性 C-H 烷基化的方法。该过程可以在温和条件下使用镍 (0) 催化剂和 N-杂环卡宾 (NHC) 配体在没有路易斯酸助催化剂的情况下进行。通过操作简单的方法合成了一系列用 1,5-己二烯稳定的 NHC 镍配合物，从而提高了官能团耐受性和杂芳烃范围。机理研究与配体-配体氢转移 (LLHT) 途径一致，其中 C-H 键活化先于决定速率的还原消除步骤。
• A microwave assisted synthesis of benzoxazoles from carboxylic acids
  作者：Giammario Nieddu、Giampaolo Giacomelli

  DOI：10.1016/j.tet.2012.10.084

  日期：2013.1

  A series of various poly-substituted benzoxazoles were synthesized starting from readily available carboxylic acids. The method is based on TCT (cyanuric chloride)/microwave acid activation and it is characterized by mild conditions, allowing for a wide range of starting materials and functionalization of final products. (c) 2012 Elsevier Ltd. All rights reserved.