2-(2-acetyl-naphthalen-1-yl)nicotinic acid ethyl ester | 638169-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-acetyl-naphthalen-1-yl)nicotinic acid ethyl ester
• 英文别名: Ethyl 2-(2-acetylnaphthalen-1-yl)pyridine-3-carboxylate
• CAS: 638169-44-5
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: FRTFQYJKVUQXOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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-acetyl-naphthalen-1-yl)nicotinic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到2-(2-acetyl-naphthalen-1-yl)-nicotinic acid
  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-乙酰基-1-萘酚 在 吡啶 、 barium dihydroxide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 2-(2-acetyl-naphthalen-1-yl)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

• Novel Extension of Meyers' Methodology:  Stereoselective Construction of Axially Chiral 7,5-Fused Bicyclic Lactams
  作者：Maël Penhoat、Vincent Levacher、Georges Dupas

  DOI：10.1021/jo035195i

  日期：2003.11.1

  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.