phenethyl 2-(naphthalen-2-yl)acetate | 1181398-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phenethyl 2-(naphthalen-2-yl)acetate
• 英文别名: 2-Phenylethyl 2-naphthalen-2-ylacetate；2-phenylethyl 2-naphthalen-2-ylacetate
• CAS: 1181398-53-7
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: WXTDEZGPKCCUCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenethyl 2-(naphthalen-2-yl)acetate 、 2-苯基溴化甲基苯 在 caesium hydroxide monohydrate 、 2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以81%的产率得到(R)-phenethyl 3-(biphenyl-2-yl)-2-(naphthalen-2-yl)propanoate
  参考文献：
  名称：

  Phase-transfer catalyzed asymmetric arylacetate alkylation

  摘要：

  Phenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts with alkyl halides in high yield with excellent enantioselectivity (84-99% ee) following recrystallization. Cinchonidine (CD) derived catalyst gave the (R)-product and cinchonine (CN) catalyst produced the (S)-product. The phenethyl (PE) ester group is removed, using ammonium formate and catalytic Pd/C, to give alkylated carboxylic acid products in high selectivity. The utility of the approach is demonstrated by a direct synthesis of (S)-naproxen(TM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.090
• 作为产物：
  描述：

  苯乙醇 、 2-萘乙酸 在 4-二甲氨基吡啶 、 diisopropylethyl amine 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 以87%的产率得到phenethyl 2-(naphthalen-2-yl)acetate
  参考文献：
  名称：

  Phase-transfer catalyzed asymmetric arylacetate alkylation

  摘要：

  Phenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts with alkyl halides in high yield with excellent enantioselectivity (84-99% ee) following recrystallization. Cinchonidine (CD) derived catalyst gave the (R)-product and cinchonine (CN) catalyst produced the (S)-product. The phenethyl (PE) ester group is removed, using ammonium formate and catalytic Pd/C, to give alkylated carboxylic acid products in high selectivity. The utility of the approach is demonstrated by a direct synthesis of (S)-naproxen(TM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.090

文献信息

• Phase-transfer catalyzed asymmetric arylacetate alkylation
  作者：Merritt B. Andrus、Kaid C. Harper、Michael A. Christiansen、Meisha A. Binkley

  DOI：10.1016/j.tetlet.2009.05.090

  日期：2009.8

  Phenethyl arylacetates are alkylated under phase-transfer conditions with cinchona catalysts with alkyl halides in high yield with excellent enantioselectivity (84-99% ee) following recrystallization. Cinchonidine (CD) derived catalyst gave the (R)-product and cinchonine (CN) catalyst produced the (S)-product. The phenethyl (PE) ester group is removed, using ammonium formate and catalytic Pd/C, to give alkylated carboxylic acid products in high selectivity. The utility of the approach is demonstrated by a direct synthesis of (S)-naproxen(TM). (C) 2009 Elsevier Ltd. All rights reserved.