2-乙酰基-3-甲氧基苯基二乙基氨基甲酸酯 | 211449-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基-3-甲氧基苯基二乙基氨基甲酸酯
• 英文名称: Diethyl-carbamic acid 2-acetyl-3-methoxy-phenyl ester
• 英文别名: (2-acetyl-3-methoxyphenyl) N,N-diethylcarbamate
• CAS: 211449-28-4
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: IOFYOYMWEMAVMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-乙酰基-3-甲氧基苯基二乙基氨基甲酸酯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以72%的产率得到1-(2-羟基-6-甲氧基苯基)乙基-1-酮
  参考文献：
  名称：

  Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

  摘要：

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00977-0
• 作为产物：
  描述：

  3-methoxyphenyl N,N-diethylcarbamate 、 乙酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 生成 2-乙酰基-3-甲氧基苯基二乙基氨基甲酸酯
  参考文献：
  名称：

  Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

  摘要：

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00977-0

文献信息

• Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins
  作者：Alexey V. Kalinin、Alcides J.M. da Silva、Claudio C. Lopes、Rosangela S.C. Lopes、Victor Snieckus

  DOI：10.1016/s0040-4039(98)00977-0

  日期：1998.7

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.