ethyl 8-(4-methoxyphenyl)-6-oxooctanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 8-(4-methoxyphenyl)-6-oxooctanoate
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: CEXKTSWWQBHJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙基5-碘戊酸酯 在 5% Pd(OH)₂/C 、 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 52.3h， 生成 ethyl 8-(4-methoxyphenyl)-6-oxooctanoate
  参考文献：
  名称：

  SYNTHESIS OF MULTI-FUNCTIONALIZED KETONES THROUGH THE FUKUYAMA COUPLING REACTION CATALYZED BY PEARLMAN'S CATALYST: PREPARATION OF ETHYL 6-OXOTRIDECANOATE

  摘要：

  DOI：

  10.15227/orgsyn.084.0285

文献信息

• A novel synthesis of functionalized ketones via a nickel-catalyzed coupling reaction of zinc reagents with thiolesters
  作者：Toshiaki Shimizu、Masahiko Seki

  DOI：10.1016/s0040-4039(01)02296-1

  日期：2002.2

  Treatment of thiolesters with zinc reagents in the presence of Ni(acac)2 provided a variety of functionalized ketones in good yields. This new protocol was successfully applied to the synthesis of (+)-biotin to allow for a practical installation of the carboxybutyl chain.

  在Ni（acac）2的存在下用锌试剂处理巯基酯可提供多种功能化的酮，收率很高。此新协议已成功应用于（+）-生物素的合成，以允许实际安装羧基丁基链。
• Pd(OH)₂/C (Pearlman's Catalyst):  A Highly Active Catalyst for Fukuyama, Sonogashira, and Suzuki Coupling Reactions
  作者：Yoshikazu Mori、Masahiko Seki

  DOI：10.1021/jo0265277

  日期：2003.2.1

  Treatment of thiol esters 1 with zinc reagent 2 in the presence of a small amount (
• Palladium on charcoal-catalyzed Fukuyama coupling reaction
  作者：Toshiaki Shimizu、Masahiko Seki

  DOI：10.1016/s0040-4039(00)01984-5

  日期：2001.1

  The Pd/C-catalyzed coupling reactions of thiol esters 1 with a zinc reagent 2 were accomplished in the presence of DMF leading to the polyfunctional ketones 3 in good yields under mild reaction conditions. The protocol was applied to the coupling reaction of a thiolactone 4c with a zinc reagent 2 to provide, after dehydration, a dehydrobiotin derivative 5c in 94% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.