benzyl (3-(4-fluorophenyl)-3-oxopropyl)carbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (3-(4-fluorophenyl)-3-oxopropyl)carbamate
• 英文别名: benzyl N-[3-(4-fluorophenyl)-3-oxopropyl]carbamate
• 化学式: C₁₇H₁₆FNO₃
• 分子量: 301.317
• InChiKey: KXOGLQLBTAESFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 四氧化锇 、 N-甲基吲哚酮 、 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 benzyl (3-(4-fluorophenyl)-3-oxopropyl)carbamate
  参考文献：
  名称：

  CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines

  摘要：

  A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to P-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.039

文献信息

• Rapid Access to γ-Amino-α-aryl Alcohol Scaffolds via an Enamine-Based Heck Coupling
  作者：Bowen Li、Gregory P. Tochtrop

  DOI：10.1021/acs.joc.1c03056

  日期：2022.3.4

  inhibitors directed toward a critical family of metabolic enzymes. Here we report the transformation of simple aryl halides to a highly functionalized benzyl (3-oxo-3-arylpropyl)carbamate intermediate that can rapidly be converted to a high value γ-amino-α-aryl alcohol. This chemistry is realized through a two-step process involving an enamine-based Heck coupling (EBHC) followed by a one-pot catalytic

  γ-氨基-α-芳基醇是设计针对关键代谢酶家族的抑制剂的关键官能团。在这里，我们报告了将简单的芳基卤化物转化为高度官能化的苄基 (3-氧代-3-芳丙基) 氨基甲酸酯中间体，该中间体可以快速转化为高价值的 γ-氨基-α-芳基醇。这种化学反应是通过一个两步过程实现的，包括基于烯胺的 Heck 偶联 (EBHC)，然后是一锅催化 Cbz 脱保护和 EBHC 产物的酮还原。
• Direct Acylation of Aryl Bromides with Aldehydes by Palladium Catalysis
  作者：Jiwu Ruan、Ourida Saidi、Jonathan A. Iggo、Jianliang Xiao

  DOI：10.1021/ja804351z

  日期：2008.8.13

  A new protocol for the direct acylation of aryl bromides with aldehydes is established. It appears to involve palladium-amine cooperative catalysis, affording synthetically important alkyl aryl ketones in moderate to excellent yields in a straightforward 7 manner, and broadening the scope of metal-catalyzed coupling reactions,