methyl 4-(1-carboxy-1-methylethyl)-2-phenyl-4H-pyridine-1-carboxylate | 868620-97-7

• 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: methyl 4-(1-carboxy-1-methylethyl)-2-phenyl-4H-pyridine-1-carboxylate
• 英文别名: 2-(1-methoxycarbonyl-2-phenyl-4H-pyridin-4-yl)-2-methylpropanoic acid
• CAS: 868620-97-7
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: ZKTSASDTEVUUKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(1-carboxy-1-methylethyl)-2-phenyl-4H-pyridine-1-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以35%的产率得到
  参考文献：
  名称：

  Selective functionalizations of 2-phenylpyridine: lactones upon organic versus organometallic activations

  摘要：

  2-Phenylpyridine activated by chromium tricarbonyl reacts with bis(TMS) ketene acetals to give pyridine-substituted bicyclic gamma-lactones. On the other hand, its reaction with the same acetals leads, upon activation with methylchloroformate, to dihydropyridines which can be oxidized to highly substituted, lactone-containing piperidines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.006
• 作为产物：
  描述：

  2-苯基吡啶 、 双三甲基硅基二甲基烯酮乙醛 、 氯甲酸甲酯 反应 12.0h， 以35%的产率得到methyl 4-(1-carboxy-1-methylethyl)-2-phenyl-4H-pyridine-1-carboxylate
  参考文献：
  名称：

  Selective functionalizations of 2-phenylpyridine: lactones upon organic versus organometallic activations

  摘要：

  2-Phenylpyridine activated by chromium tricarbonyl reacts with bis(TMS) ketene acetals to give pyridine-substituted bicyclic gamma-lactones. On the other hand, its reaction with the same acetals leads, upon activation with methylchloroformate, to dihydropyridines which can be oxidized to highly substituted, lactone-containing piperidines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.006

文献信息

• Bis(trimethylsilyl)ketene Acetals as C,O-Dinucleophiles: One-Pot Formation of Polycyclic γ- and δ-Lactones from Pyridines and Pyrazines
  作者：Henri Rudler、Bernard Denise、Yiming Xu、Andrée Parlier、Jacqueline Vaissermann

  DOI：10.1002/ejoc.200500162

  日期：2005.9

  interaction with both nitrogen atoms, of polycyclic γ-lactones, a reaction formally reminiscent of the double nucleophilic addition of the same ketene acetals to (arene)tricarbonylchromium complexes. Most of the new structures were assigned through X-ray crystal structure determinations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  双（三甲基甲硅烷基）烯酮缩醛在化学计量量的氯甲酸甲酯存在下与吡啶、喹啉和异喹啉反应，以令人满意的产率得到相应的二氢吡啶-、二氢喹啉-和二氢异喹啉-取代的羧酸。加成反应的区域选择性和非对映选择性以及旋转异构体的存在或不存在都已确定。分离出的酸与过酸反应，通过分子内反应生成 β-羟基-δ-内酯。类似的内酯化也可以直接从氮杂芳族化合物与硅胶、碘或溴的一锅反应中产生。在这些情况下，产生了δ-内酯或β-卤代-δ-内酯。吡嗪在这些转变中的行为是奇特的，由于氯甲酸甲酯本身通过与两个氮原子的相互作用诱导多环γ-内酯的形成，这种反应形式上让人想起相同的烯酮缩醛与（芳烃）三羰基铬配合物的双亲核加成反应。大多数新结构是通过 X 射线晶体结构测定确定的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Selective functionalizations of 2-phenylpyridine: lactones upon organic versus organometallic activations
  作者：Yiming Xu、Eugenia Aldeco-Pérez、Henri Rudler、Andrée Parlier、Cecilio Alvarez

  DOI：10.1016/j.tetlet.2006.05.006

  日期：2006.7

  2-Phenylpyridine activated by chromium tricarbonyl reacts with bis(TMS) ketene acetals to give pyridine-substituted bicyclic gamma-lactones. On the other hand, its reaction with the same acetals leads, upon activation with methylchloroformate, to dihydropyridines which can be oxidized to highly substituted, lactone-containing piperidines. (c) 2006 Elsevier Ltd. All rights reserved.