dimethyl 2-(2-bromo-4,5-dimethoxybenzylidene)malonate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl 2-(2-bromo-4,5-dimethoxybenzylidene)malonate
• 英文别名: Dimethyl 2-[(2-bromo-4,5-dimethoxyphenyl)methylidene]propanedioate
• 化学式: C₁₄H₁₅BrO₆
• 分子量: 359.173
• InChiKey: DKFZTAIDWHFGJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(2-bromo-4,5-dimethoxybenzylidene)malonate 在 sodium hydride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-(二叔丁基膦)联苯 作用下， 以 1,4-二氧六环 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 4.66h， 生成 dimethyl [(6,7-dimethoxy-4-methyl-3-oxido-1H-2,3-benzoxazin-1-yl)methyl]malonate
  参考文献：
  名称：

  Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

  摘要：

  The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)(2)/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.091
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 吗啉 、 溴 、 苯甲酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 7.0h， 生成 dimethyl 2-(2-bromo-4,5-dimethoxybenzylidene)malonate
  参考文献：
  名称：

  Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

  摘要：

  The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)(2)/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.091

文献信息

• Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
  作者：Andrey A. Mikhaylov、Alexander D. Dilman、Roman A. Novikov、Yulia A. Khoroshutina、Marina I. Struchkova、Dmitry E. Arkhipov、Yulia V. Nelyubina、Andrey A. Tabolin、Sema L. Ioffe

  DOI：10.1016/j.tetlet.2015.10.091

  日期：2016.1

  The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)(2)/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.