4,7-dibromo-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-endo-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,7-dibromo-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-endo-carboxylic acid methyl ester
• 英文别名: methyl (1S,4S,5R)-4,7-dibromo-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carboxylate
• 化学式: C₉H₈Br₂O₄
• 分子量: 339.968
• InChiKey: XPVKWAZPTYMVMH-MFCLVGODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,7-dibromo-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-endo-carboxylic acid methyl ester 在 四(三苯基膦)钯 sodium methylate 作用下， 以 甲苯 为溶剂， 生成 dimethyl 4-phenylphthalate
  参考文献：
  名称：

  Pd catalyzed cross-coupling reactions of the cycloadducts from 3,5-dibromo-2-pyrone and their synthetic applications towards various mono- and polycyclic compounds

  摘要：

  Bicylolactones from Diels-Alder (D A) cycloadditions of 3,5-dibromo-2-pyrone can undergo various palladium catalyzed cross Coupling reactions to afford a series of alkenyl, alkynyl and aryl bicyclolactones. The resulting coupled products can be readily converted into various 3-OH cyclohexenes via lactone ring openings, while those bearing dienyl units underwent highly diastereoselective D-A cycloadditions with selected dienophiles to furnish multiply functionalized polycarbocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01126-7
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 3,5-二溴-2H-吡喃-2-酮 以 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到4,7-dibromo-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-endo-carboxylic acid methyl ester
  参考文献：
  名称：

  3,5-二溴-2-吡酮的Diels-Alder环加成反应：一种新的环境二烯。

  摘要：

  用一系列电子和空间上不同的亲二烯体研究了3,5-二溴-2-吡喃酮的DA环加成反应。我们的结果表明，它是一种高效的环境二烯，比单溴-2-吡喃酮具有更高的反应性和立体选择性，因此能够以比单溴-2-吡喃酮更高的化学收率和内/外比生成各种双环加合物。这项研究的另一个有趣特征是，可以独立地控制环加合物上的两个溴基团，以产生其他合成上有用的双环内酯。

  DOI：

  10.1021/jo015804r

文献信息

• One step preparation of bromo-2-pyrones via bromo-decarboxylation of 2-pyrone-carboxylic acids
  作者：Cheon-Gyu Cho、Jung-Sang Park、In-Hak Jung、Haiwon Lee

  DOI：10.1016/s0040-4039(00)02182-1

  日期：2001.2

  Synthetically valuable 3-brorno-2-pyrone, 3-bromocoumarin, 5-bromo-2-pyrone, and 3,5-dibromo-2-pyrone were prepared in one step from readily available 2-pyrone-carboxylic acids via bromo-decarboxylation in good to fair yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diels−Alder Cycloadditions of 3,5-Dibromo-2-pyrone:  A New Ambident Diene
  作者：Cheon-Gyu Cho、Yong-Woo Kim、Young-Kwan Lim、Jung-Sang Park、Haiwon Lee、Sangman Koo

  DOI：10.1021/jo015804r

  日期：2002.1.1

  D-A cycloadditions of 3,5-dibromo-2-pyrone were investigated with a series of electronically and sterically distinct dienophiles. Our results showed that it is a highly potent ambident diene, being more reactive and stereoselective than monobromo-2-pyrones, and thus capable of generating a variety of bicycloadducts in much higher chemical yields and endo/exo ratios than monobromo-2-pyrones. Another

  用一系列电子和空间上不同的亲二烯体研究了3,5-二溴-2-吡喃酮的DA环加成反应。我们的结果表明，它是一种高效的环境二烯，比单溴-2-吡喃酮具有更高的反应性和立体选择性，因此能够以比单溴-2-吡喃酮更高的化学收率和内/外比生成各种双环加合物。这项研究的另一个有趣特征是，可以独立地控制环加合物上的两个溴基团，以产生其他合成上有用的双环内酯。
• Pd catalyzed cross-coupling reactions of the cycloadducts from 3,5-dibromo-2-pyrone and their synthetic applications towards various mono- and polycyclic compounds
  作者：Hyun-Soo Lee、Daesung Kim、Hoshik Won、Jung Hoon Choi、Haiwon Lee、Cheon-Gyu Cho

  DOI：10.1016/s0040-4039(02)01126-7

  日期：2002.8

  Bicylolactones from Diels-Alder (D A) cycloadditions of 3,5-dibromo-2-pyrone can undergo various palladium catalyzed cross Coupling reactions to afford a series of alkenyl, alkynyl and aryl bicyclolactones. The resulting coupled products can be readily converted into various 3-OH cyclohexenes via lactone ring openings, while those bearing dienyl units underwent highly diastereoselective D-A cycloadditions with selected dienophiles to furnish multiply functionalized polycarbocycles. (C) 2002 Elsevier Science Ltd. All rights reserved.