2-(2',3'-dimethoxybiphenyl-2-yl)-N-methylacetamide | 185985-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2',3'-dimethoxybiphenyl-2-yl)-N-methylacetamide
• 英文别名: 2-[2-(2,3-dimethoxyphenyl)phenyl]-N-methylacetamide
• CAS: 185985-94-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: FMIUTLFXVODBTP-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  464.8±45.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2',3'-dimethoxybiphenyl-2-yl)-N-methylacetamide 在 三氟化硼乙醚 、 B-溴代邻苯二氧硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以96%的产率得到2-(2',3'-dihydroxybiphenyl-2-yl)-N-methylacetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines

  摘要：

  Described herein is the first total synthesis and structural confirmation of cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluation of both natural products. Finally, the preparation and biological evaluation of novel dioxoaporphine analogues is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.035
• 作为产物：
  描述：

  2,3-二甲氧基苯硼酸 在 四(三苯基膦)钯 氰化钠 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 20.0h， 生成 2-(2',3'-dimethoxybiphenyl-2-yl)-N-methylacetamide
  参考文献：
  名称：

  钯（0）铃木交叉偶联反应是合成阿片类药物的关键步骤

  摘要：

  我们报告了一种灵活的方法，可以基于钯（0）催化的苯硼酸与空间受阻的2-溴苯基乙酸酯或溴代苯基乙酰胺的铃木交叉偶联，对4,5-二氧杂卟啉进行全合成，然后依次进行二环化的联芳基乙酰胺由草酰氯/路易斯酸。4，5-二氧杂卟啉的还原提供了对磷腈，脱氢紫杉醇和4-羟基-脱氢紫杉醇的化学选择性进入。（±）为一个三步骤的总合成- ø，ö还报道从容易获得的前体'-dimethylapomorphine。

  DOI：

  10.1016/j.tet.2004.05.014

文献信息

• A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential ring formation from arylacetamides
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4039(97)82963-2

  日期：1996.12

  Cyclization of biarylacetamides to their phenanthrene derivatives is promoted by oxalyl chloride/stannyl chloride. The reaction proceeds with a second cyclization in which the oxalyl fragment acts as an alpha-dicarbonyl transfer agent to give 4,5-dioxoaporphine alkaloids in a single step. This double cyclization was also applied to aryloxyphenyl acetamides to give the corresponding 3,4-dioxocularine alkaloids. Decarbonylated aristocularine alkaloids were also formed in this case. Copyright (C) 1996 Elsevier Science Ltd
• Sequential bicyclization of biphenyl acetamides promoted by (COCl)2/SnCl4. Total synthesis of 4,5-dioxoaporphines
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4020(97)00923-x

  日期：1997.10

  The reaction of biphenyl acetamides with excess of oxalyl chloride/stannyl chloride offers a one pot, high-yield entry to 4,5-dioxoaporphine alkaloids. This strategy has been applied to the synthesis of 4,5-dioxodehydrocorydine starting from 1-iodo-2,3-dimethoxybenzene. The cytotoxicity of tetraoxygenated 4,5-dioxoaporphines has been evaluated. (C) 1997 Elsevier Science Ltd.
• The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids
  作者：R Suau、R Rico、F Nájera、F.J Ortiz-López、J.M López-Romero、M Moreno-Mañas、A Roglans

  DOI：10.1016/j.tet.2004.05.014

  日期：2004.6

  of phenylboronic acids with sterically hindered 2-bromo phenyl acetates or bromo phenyl acetamides, followed by sequential bicyclization of biarylacetamides promoted by oxalyl chloride/Lewis acid. The reduction of 4,5-dioxoaporphines provides a chemoselective entry to aporphines, dehydroaporphines and 4-hydroxy-dehydroaporphines. A three-steps total synthesis for (±)-O,O′-dimethylapomorphine from readily

  我们报告了一种灵活的方法，可以基于钯（0）催化的苯硼酸与空间受阻的2-溴苯基乙酸酯或溴代苯基乙酰胺的铃木交叉偶联，对4,5-二氧杂卟啉进行全合成，然后依次进行二环化的联芳基乙酰胺由草酰氯/路易斯酸。4，5-二氧杂卟啉的还原提供了对磷腈，脱氢紫杉醇和4-羟基-脱氢紫杉醇的化学选择性进入。（±）为一个三步骤的总合成- ø，ö还报道从容易获得的前体'-dimethylapomorphine。
• Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines
  作者：Mark A. Elban、Jean C. Chapuis、Mei Li、Sidney M. Hecht

  DOI：10.1016/j.bmc.2007.06.035

  日期：2007.9

  Described herein is the first total synthesis and structural confirmation of cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluation of both natural products. Finally, the preparation and biological evaluation of novel dioxoaporphine analogues is described. (c) 2007 Elsevier Ltd. All rights reserved.