benzyl (3-(4-methoxyphenyl)-3-oxopropyl)carbamate | 1041467-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (3-(4-methoxyphenyl)-3-oxopropyl)carbamate
• 英文别名: benzyl N-[3-(4-methoxyphenyl)-3-oxopropyl]carbamate
• CAS: 1041467-40-6
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: WRYIXMOBTBQJRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (3-(4-methoxyphenyl)-3-oxopropyl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、1.38 MPa 条件下， 反应 48.0h， 以65%的产率得到3-amino-1-(4-methoxyphenyl)propan-1-ol
  参考文献：
  名称：

  通过基于烯胺的 Heck 偶联快速获得 γ-氨基-α-芳基醇支架

  摘要：

  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。

  DOI：

  10.1021/acs.joc.1c03056
• 作为产物：
  描述：

  4-氯苯甲醚 、 N-苄氧羰基-3-氨基丙醛 在 四氢吡咯 、 2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以74%的产率得到benzyl (3-(4-methoxyphenyl)-3-oxopropyl)carbamate
  参考文献：
  名称：

  Direct Acylation of Aryl Chlorides with Aldehydes by Palladium−Pyrrolidine Co-catalysis

  摘要：

  A palladium catalyst system has been developed that allows for the direct acylation of aryl chlorides with aldehydes. The choice of ligand, as well as the presence of pyrrolidine and molecular sieves is shown to be critical to the catalysis, which appears to proceed via an enamine intermediate. The reaction was successful for a wide range of aryl chlorides and tolerant of functionality on the aldehyde component, giving easy access to alkyl aryl ketones in modest to good yields.

  DOI：

  10.1021/ol101466g

文献信息

• 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,
• Direct Acylation of Aryl Chlorides with Aldehydes by Palladium−Pyrrolidine Co-catalysis
  作者：Paul Colbon、Jiwu Ruan、Mark Purdie、Jianliang Xiao

  DOI：10.1021/ol101466g

  日期：2010.8.20

  A palladium catalyst system has been developed that allows for the direct acylation of aryl chlorides with aldehydes. The choice of ligand, as well as the presence of pyrrolidine and molecular sieves is shown to be critical to the catalysis, which appears to proceed via an enamine intermediate. The reaction was successful for a wide range of aryl chlorides and tolerant of functionality on the aldehyde component, giving easy access to alkyl aryl ketones in modest to good yields.
• 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。