2-乙酰基萘-1-基二乙基氨基甲酸酯 | 211449-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-乙酰基萘-1-基二乙基氨基甲酸酯
• 英文名称: (2-acetylnaphthalen-1-yl) N,N-diethylcarbamate
• CAS: 211449-32-0
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: YCZXIAHVLYKXHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  434.849±37.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.144±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰基萘-1-基二乙基氨基甲酸酯 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 4-羟基-2H-苯并[H]色烯-2-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：

  2-乙酰基-1-萘酚 、 N,N-二乙基氯甲酰胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以86%的产率得到2-乙酰基萘-1-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.