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(S)-phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate | 1181399-48-3

中文名称
——
中文别名
——
英文名称
(S)-phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate
英文别名
2-phenylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
(S)-phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate化学式
CAS
1181399-48-3
化学式
C22H22O3
mdl
——
分子量
334.415
InChiKey
IQGJWFCCXNOEPZ-INIZCTEOSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.1
  • 重原子数:
    25
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.23
  • 拓扑面积:
    35.5
  • 氢给体数:
    0
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    (S)-phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate 在 palladium 10% on activated carbon 、 甲酸铵 、 palladium diacetate 作用下, 以 甲醇 为溶剂, 反应 17.0h, 以91%的产率得到萘普生
    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:
    苯乙醇萘普生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 22.0h, 以93%的产率得到(S)-phenethyl 2-(6-methoxynaphthalen-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
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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.
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