2-allyl-N,N-diethyl-3,5-dimethoxybenzamide | 150130-06-6

• 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-allyl-N,N-diethyl-3,5-dimethoxybenzamide
• 英文别名: Benzamide, N,N-diethyl-3,5-dimethoxy-2-(2-propenyl)-；N,N-diethyl-3,5-dimethoxy-2-prop-2-enylbenzamide
• CAS: 150130-06-6
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: SWZCYCHFGWHPGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-N,N-diethyl-3,5-dimethoxybenzamide 在 四氧化锇 、 双氧水 作用下， 生成 2-(2,3-Dihydroxy-propyl)-N,N-diethyl-3,5-dimethoxy-benzamide
  参考文献：
  名称：

  Anomalous Face-Selectivity in Sharpless Asymmetric Dihydroxylation of o-Allylbenzamides

  摘要：

  DOI：

  10.1021/jo9607323
• 作为产物：
  描述：

  N,N-diethyl-3,5-dimethoxybenzamide 、 3-溴丙烯 生成 2-allyl-N,N-diethyl-3,5-dimethoxybenzamide
  参考文献：
  名称：

  Anomalous Face-Selectivity in Sharpless Asymmetric Dihydroxylation of o-Allylbenzamides

  摘要：

  DOI：

  10.1021/jo9607323

文献信息

• Regioselective ortho-alkylation of N,N-diethylbenzamides via lithiation and copper transmetalation
  作者：Dario Pini、Stefano Superchi、Piero Salvadori

  DOI：10.1016/0022-328x(93)83206-b

  日期：1993.6

  One-pot ortho-lithiation and copper transmetalation with CuCN.LiCl of N,N-diethylbenzamides afford the corresponding aryl cyanocuprate, which gives coupling with some aliphatic halides in fair to good yields.
• Formal Synthesis of Angiogenesis Inhibitor NM-3
  作者：William E. Bauta、Dennis P. Lovett、William R. Cantrell、Brian D. Burke

  DOI：10.1021/jo034165c

  日期：2003.7.1

  We report the formal synthesis of angiogenesis inhibitor NM-3 (1) in six steps from either of the 2,4-dimethoxyhalobenzenes 13a,b or 3,5-dimethoxychlorobenzene (13c). The first key reaction is the regiospecific alkylation/rearrangement between the aryne derived from 13a-c with sodium diethylmalonate in THF to produce diester 11, which after hydrolysis and cyclization affords homophthalic anhydride 3. The second is the reaction of anhydride 3 with either ethyl 2-methylmalonate (28a), in the presence of 1,1'-carbonyldiimidazole, or ethyl-2-methylmalonyl chloride (28b) under basic conditions to afford key isocoumarin 27. The conversion of 27 constitutes a formal synthesis of NM-3.
• Anomalous Face-Selectivity in Sharpless Asymmetric Dihydroxylation of <i>o</i>-Allylbenzamides
  作者：Piero Salvadori、Stefano Superchi、Filippo Minutolo

  DOI：10.1021/jo9607323

  日期：1996.1.1