2-(2-acetylphenyl)nicotinic acid ethyl ester | 638169-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-acetylphenyl)nicotinic acid ethyl ester
• 英文别名: Ethyl 2-(2-acetylphenyl)pyridine-3-carboxylate
• CAS: 638169-43-4
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: XLTIJAJHMIXSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-acetylphenyl)nicotinic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 96.0h， 生成 (aS,3R,13bS)-13b-methyl-3-phenyl-2,3-dihydro-13bH-benz[c]oxazolo[3,2-a]pyrido[2,3-e]azepin-5-one
  参考文献：
  名称：

  Novel Extension of Meyers' Methodology:  Stereoselective Construction of Axially Chiral 7,5-Fused Bicyclic Lactams

  摘要：

  A novel extension of Meyer's lactamization is reported for the preparation of seven-membered ring lactams 1a-d incorporating a biaryl unit. The required keto-esters 2a-c were readily accessible via the Suzuki coupling reaction. A borylation-Suzuki coupling (BSC) sequence was successfully developed for the high-yielding preparation of keto-ester 2d. Cyclization of the resulting keto-esters 2a-d or keto-acids 5a,c,d in the presence of (R)-phenylglycinol afforded the desired lactams 1a-d in high yields (72-93%) and excellent diastereoselectivities (>95%). This methodology provides a facile stereoselective access to new axially chiral bridged biaryls.

  DOI：

  10.1021/jo035195i
• 作为产物：
  描述：

  2-氯烟酰氯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 60.0h， 生成 2-(2-acetylphenyl)nicotinic acid ethyl ester
  参考文献：
  名称：

  Novel Extension of Meyers' Methodology:  Stereoselective Construction of Axially Chiral 7,5-Fused Bicyclic Lactams

  摘要：

  A novel extension of Meyer's lactamization is reported for the preparation of seven-membered ring lactams 1a-d incorporating a biaryl unit. The required keto-esters 2a-c were readily accessible via the Suzuki coupling reaction. A borylation-Suzuki coupling (BSC) sequence was successfully developed for the high-yielding preparation of keto-ester 2d. Cyclization of the resulting keto-esters 2a-d or keto-acids 5a,c,d in the presence of (R)-phenylglycinol afforded the desired lactams 1a-d in high yields (72-93%) and excellent diastereoselectivities (>95%). This methodology provides a facile stereoselective access to new axially chiral bridged biaryls.

  DOI：

  10.1021/jo035195i

文献信息

• Developments in Meyers’ Lactamization Methodology: En Route to Bi(hetero)aryl Structures with Defined Axial Chirality
  作者：Svetlana Postikova、Mohamad Sabbah、Daniel Wightman、Ich Tuan Nguyen、Morgane Sanselme、Thierry Besson、Jean-François Brière、Sylvain Oudeyer、Vincent Levacher

  DOI：10.1021/jo401259w

  日期：2013.8.16

  Highly atroposelective Meyers' lactamization promoted by pivalic acid under microwave irradiation is reported which allows the construction of nonracemic substituted-dibenzo(di)azepine derivatives through a center to axial chirality transfer principle, controlling the otherwise configurationally labile biaryl axis. This approach provides a straightforward entry to enantioenriched analogues of biorelevant architectures.