4,5-dichloro-6-{[(3-methoxybenzyl)oxy]methyl}-7-{3-[(4-methoxybenzyl)oxy]prop-1-yn-1-yl}-2-tosylisoindoline | 1510816-03-1

• 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: 4,5-dichloro-6-{[(3-methoxybenzyl)oxy]methyl}-7-{3-[(4-methoxybenzyl)oxy]prop-1-yn-1-yl}-2-tosylisoindoline
• 英文别名: 4,5-Dichloro-6-[(4-methoxyphenyl)methoxymethyl]-7-[3-[(4-methoxyphenyl)methoxy]prop-1-ynyl]-2-(4-methylphenyl)sulfonyl-1,3-dihydroisoindole；4,5-dichloro-6-[(4-methoxyphenyl)methoxymethyl]-7-[3-[(4-methoxyphenyl)methoxy]prop-1-ynyl]-2-(4-methylphenyl)sulfonyl-1,3-dihydroisoindole
• CAS: 1510816-03-1
• 化学式: C₃₅H₃₃Cl₂NO₆S
• 分子量: 666.622
• InChiKey: AOAHFDNJPXEPFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-bis{6-[(4-methoxybenzyl)oxy]hexa-2,4-diyn-1-yl}-4-methylbenzenesulfonamide 在 dilithium tetrachlorocuprate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以77%的产率得到4,5-dichloro-6-{[(3-methoxybenzyl)oxy]methyl}-7-{3-[(4-methoxybenzyl)oxy]prop-1-yn-1-yl}-2-tosylisoindoline
  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