(S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate | 1117792-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate
• 英文别名: t-Bu-Nicox；methyl 6-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine-3-carboxylate
• CAS: 1117792-25-2
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: NVWFDWZVUFFYNR-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以72 %的产率得到(S)-6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinic acid
  参考文献：
  名称：

  Enantioselective Heterogeneous Heck–Matsuda Reaction with Polymer-Supported PyOx Ligands

  摘要：

  Carboxymethyl C5-functionalized pyridine-oxazoline (PyOx) ligands are immobilized onto Merrifield and Wang resins utilizing three distinct strategies. The immobilized PyOx ligands are employed in the Pd-catalyzed heterogeneous Heck–Matsuda reaction for the desymmetrization of 3-cyclopenten-1-ol, resulting in the production of 20 examples of aryl-penten-1-ols with yields reaching up to 87%, and enantiomeric ratios ranging between 90:10 and 99:1. These outcomes align with those achieved by the homogeneous counterparts, demonstrating comparable efficiency. Subsequent recycling analysis reveals a progressive decline in catalyst efficiency upon reuse, suggesting the formation of palladium black on the catalyst surface.

  DOI：

  10.1055/a-2284-5030
• 作为产物：
  描述：

  5-(甲氧羰基)-2-吡啶羧酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 85.0h， 生成 (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate
  参考文献：
  名称：

  钯催化的芳基硼酸对环酮亚胺的对映选择性加成

  摘要：

  像Nicox一样狡猾：已开发出一种钯催化的芳基硼酸加成酮亚胺，以有效地提供高达99％的收率和96％ee的产品。反应可以在有氧条件下和未纯化的三氟乙醇（TFE）下进行。几步合成了带有手性α-叔胺的吡咯烷化合物，且不损失对映选择性。TFA ＝三氟乙酸盐。

  DOI：

  10.1002/anie.201302861
• 作为试剂：
  描述：

  3-环戊烯-1-醇 、 benzenediazonium tetrafluoroborate 在 2,6-二叔丁基-4-甲基吡啶 、 palladium(II) trifluoroacetate 、 (S)-methyl 6-(4-(tert-butyl)-4,5-dihydrooxazol-2-yl)nicotinate 作用下， 以 甲醇 、 甲苯 为溶剂， 以74 %的产率得到(1S,4R)-cis-4-phenylcyclopent-2-enol
  参考文献：
  名称：

  Enantioselective Heterogeneous Heck–Matsuda Reaction with Polymer-Supported PyOx Ligands

  摘要：

  Carboxymethyl C5-functionalized pyridine-oxazoline (PyOx) ligands are immobilized onto Merrifield and Wang resins utilizing three distinct strategies. The immobilized PyOx ligands are employed in the Pd-catalyzed heterogeneous Heck–Matsuda reaction for the desymmetrization of 3-cyclopenten-1-ol, resulting in the production of 20 examples of aryl-penten-1-ols with yields reaching up to 87%, and enantiomeric ratios ranging between 90:10 and 99:1. These outcomes align with those achieved by the homogeneous counterparts, demonstrating comparable efficiency. Subsequent recycling analysis reveals a progressive decline in catalyst efficiency upon reuse, suggesting the formation of palladium black on the catalyst surface.

  DOI：

  10.1055/a-2284-5030

文献信息

• Mechanistic Studies into the Oxidative Addition of Co(I) Complexes: Combining Electroanalytical Techniques with Parameterization
  作者：Christopher Sandford、Lydia R. Fries、Tyler E. Ball、Shelley D. Minteer、Matthew S. Sigman

  DOI：10.1021/jacs.9b10771

  日期：2019.11.27

  generated Co(I) complexes has been widely utilized as a strategy to produce carbon-centered radicals when cobalt is ligated by a polydentate ligand. Changing to a bidentate ligand provides the opportunity to access discrete Co(III)-C bonded complexes for alternative reactivity, but knowledge of how ligand and/or substrate structures affect catalytic steps is pivotal to reaction design and catalyst optimization

  当钴被多齿配体连接时，有机亲电试剂氧化加成到电化学生成的 Co(I) 复合物中已被广泛用作产生碳中心自由基的策略。更改为双齿配体提供了访问离散 Co(III)-C 键合配合物以实现替代反应的机会，但了解配体和/或底物结构如何影响催化步骤对于反应设计和催化剂优化至关重要。在这方面，可以确定基本有机金属步骤的确切性质的实验研究仍然有限，特别是对于单电子氧化加成途径。在这里，我们利用循环伏安法结合模拟来获得两步卤原子提取机制的动力学和热力学性质，通过分析动力学同位素和取代基效应进行验证。可以解开复杂的哈米特关系，以了解个体对活化能垒和平衡常数的影响，以及用于建立新配体/底物组合率的预测统计模型的 DFT 衍生参数。
• A Palladium-Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic Ketimines
  作者：Guoqiang Yang、Wanbin Zhang

  DOI：10.1002/anie.201302861

  日期：2013.7.15

  Nicox: A palladium‐catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α‐tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA=trifluoroacetate.

  像Nicox一样狡猾：已开发出一种钯催化的芳基硼酸加成酮亚胺，以有效地提供高达99％的收率和96％ee的产品。反应可以在有氧条件下和未纯化的三氟乙醇（TFE）下进行。几步合成了带有手性α-叔胺的吡咯烷化合物，且不损失对映选择性。TFA ＝三氟乙酸盐。
• Enantioselective Heterogeneous Heck–Matsuda Reaction with Polymer-Supported PyOx Ligands
  作者：Carlos R. D. Correia、Julio C. Pastre、Christian L. Herrera、Rafael L. Oliveira、Rodrigo C. Silva

  DOI：10.1055/a-2284-5030

  日期：——

  Carboxymethyl C5-functionalized pyridine-oxazoline (PyOx) ligands are immobilized onto Merrifield and Wang resins utilizing three distinct strategies. The immobilized PyOx ligands are employed in the Pd-catalyzed heterogeneous Heck–Matsuda reaction for the desymmetrization of 3-cyclopenten-1-ol, resulting in the production of 20 examples of aryl-penten-1-ols with yields reaching up to 87%, and enantiomeric ratios ranging between 90:10 and 99:1. These outcomes align with those achieved by the homogeneous counterparts, demonstrating comparable efficiency. Subsequent recycling analysis reveals a progressive decline in catalyst efficiency upon reuse, suggesting the formation of palladium black on the catalyst surface.