Dimethyl 4,5-bis(prop-2-enoxy)benzene-1,2-dicarboxylate | 1419179-04-6

• 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: Dimethyl 4,5-bis(prop-2-enoxy)benzene-1,2-dicarboxylate
• 英文别名: dimethyl 4,5-bis(prop-2-enoxy)benzene-1,2-dicarboxylate
• CAS: 1419179-04-6
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: PNOBNGJXXODVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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 4,5-bis(prop-2-enoxy)benzene-1,2-dicarboxylate 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 dimethyl 4-[(2E,9E,16E)-6-oxooctadeca-2,9,16-trien-7-yl]oxy-5-prop-2-enoxybenzene-1,2-dicarboxylate
  参考文献：
  名称：

  Toward the Synthesis of Phomoidride D

  摘要：

  An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

  DOI：

  10.1021/jo302353g
• 作为产物：
  描述：

  4,5-双(羟基)邻苯二甲酸二甲酯 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以39.3%的产率得到Dimethyl 4-hydroxy-5-prop-2-enoxybenzene-1,2-dicarboxylate
  参考文献：
  名称：

  Toward the Synthesis of Phomoidride D

  摘要：

  An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

  DOI：

  10.1021/jo302353g

文献信息

• Toward the Synthesis of Phomoidride D
  作者：Graham K. Murphy、Tatsuya Shirahata、Naoto Hama、Aaron Bedermann、Ping Dong、Travis C. McMahon、Barry M. Twenter、David A. Spiegel、Ivar M. McDonald、Nobuaki Taniguchi、Munenori Inoue、John L. Wood

  DOI：10.1021/jo302353g

  日期：2013.1.18

  An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.