(R)-phenethyl 2-(naphthalen-2-yl)pent-4-enoate | 1181398-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-phenethyl 2-(naphthalen-2-yl)pent-4-enoate
• 英文别名: 2-phenylethyl (2R)-2-naphthalen-2-ylpent-4-enoate
• CAS: 1181398-95-7
• 化学式: C₂₃H₂₂O₂
• 分子量: 330.426
• InChiKey: PSPMUWDEVLGTDJ-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  phenethyl 2-(naphthalen-2-yl)acetate 、 3-溴丙烯 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63%的产率得到(R)-phenethyl 2-(naphthalen-2-yl)pent-4-enoate
  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.