1,3-Bis(2-chloroethoxy)-5-methylbenzene | 512782-14-8

• 英文名称: 1,3-Bis(2-chloroethoxy)-5-methylbenzene
• CAS: 512782-14-8
• 化学式: C₁₁H₁₄Cl₂O₂
• 分子量: 249.137
• InChiKey: ZLKNWEJMZGUHAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  358.0±32.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-Bis(2-chloroethoxy)-5-methylbenzene 在 正丁基锂 、 乙基溴化镁 、 溴 、 哌啶乙酸盐 、 magnesium 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 68.0h， 生成 4-Methyl-8-((E)-2-nitro-propenyl)-benzo[1,2-b;5,4-b']difuran
  参考文献：
  名称：

  Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT2A/2C receptor affinity

  摘要：

  Positional modification of 2,5-dimethoxyamphetamine analogues has been studied. Specifically, the 5-alkoxy substituent was translocated to the 6-position of the phenyl nucleus. Methoxy groups were also constrained by incorporation into appended dihydrofuran and furan rings. 2,6-Dimethoxy-4-methylamphetamine had an approximately 3-fold lower affinity for the 5-HT2A compared to the parent 2,5-dimethoxy-4-methylamphetamine (DOM). The rigid compound based on the 2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran nucleus and the aromatic analogue containing the benzo[l,2-b;5,4-b']difuran nucleus possessed an approximate 7- and 27-fold increase in affinity, respectively, compared to 2,6-dimethoxy-4-methylamphetamine, the non-rigid, positional isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00306-2
• 作为产物：
  描述：

  3,5-二羟基甲苯 、 1-溴-2-氯乙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以75%的产率得到1,3-Bis(2-chloroethoxy)-5-methylbenzene
  参考文献：
  名称：

  Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT2A/2C receptor affinity

  摘要：

  Positional modification of 2,5-dimethoxyamphetamine analogues has been studied. Specifically, the 5-alkoxy substituent was translocated to the 6-position of the phenyl nucleus. Methoxy groups were also constrained by incorporation into appended dihydrofuran and furan rings. 2,6-Dimethoxy-4-methylamphetamine had an approximately 3-fold lower affinity for the 5-HT2A compared to the parent 2,5-dimethoxy-4-methylamphetamine (DOM). The rigid compound based on the 2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran nucleus and the aromatic analogue containing the benzo[l,2-b;5,4-b']difuran nucleus possessed an approximate 7- and 27-fold increase in affinity, respectively, compared to 2,6-dimethoxy-4-methylamphetamine, the non-rigid, positional isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00306-2