Diethyl-carbamic acid 2-phenylacetyl-naphthalen-1-yl ester | 211449-33-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Diethyl-carbamic acid 2-phenylacetyl-naphthalen-1-yl ester
• 英文别名: [2-(2-phenylacetyl)naphthalen-1-yl] N,N-diethylcarbamate
• CAS: 211449-33-1
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: PZKHMWCNNJFQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  Diethyl-carbamic acid 2-phenylacetyl-naphthalen-1-yl ester 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 2-羟基-3-苯基-4H-苯并[h]色烯-4-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：

  1-naphthyl N,N-diethylcarbamate 、 苯乙酰氯 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 Diethyl-carbamic acid 2-phenylacetyl-naphthalen-1-yl ester
  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.