dimethyl 5-butyl-6,7-dichloro-4-(hex-1-yn-1-yl)-1,3-dihydro-2H-indene-2,2-dicarboxylate | 1510815-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 5-butyl-6,7-dichloro-4-(hex-1-yn-1-yl)-1,3-dihydro-2H-indene-2,2-dicarboxylate
• CAS: 1510815-97-0
• 化学式: C₂₃H₂₈Cl₂O₄
• 分子量: 439.379
• InChiKey: XBWFOHWMQXYJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  dimethyl 2,2-di(nona-2,4-diyn-1-yl)malonate 在 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以70%的产率得到dimethyl 5-butyl-6,7-dichloro-4-(hex-1-yn-1-yl)-1,3-dihydro-2H-indene-2,2-dicarboxylate
  参考文献：
  名称：

  Dichlorination of (Hexadehydro-Diels–Alder Generated) Benzynes and a Protocol for Interrogating the Kinetic Order of Bimolecular Aryne Trapping Reactions

  摘要：

  The efficient dichlorination of benzynes prepared by the hexadehydro-Diels-Alder (HDDA) reaction is reported. Cycloisomerization of a triyne substrate in the presence of dilithium tetrachlorocuprate is shown to provide dichlorinated products A by capture of the benzyne intermediate. A general strategy for discerning the kinetic order of an external aryne trapping agent is presented. It merely requires measurement of the competition between bimolecular vs unimolecular trapping events (here, dichlorination vs intramolecular Diels-Alder (IMDA) reaction to give A vs B, respectively) as a function of the concentration of the trapping agent.

  DOI：

  10.1021/ol403258c