Benzene, 1-chloro-4-[[(2-chloroethyl)imino]methyl]- | 59414-48-1

• 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: Benzene, 1-chloro-4-[[(2-chloroethyl)imino]methyl]-
• 英文别名: N-(2-chloroethyl)-1-(4-chlorophenyl)methanimine
• CAS: 59414-48-1
• 化学式: C₉H₉Cl₂N
• 分子量: 202.083
• InChiKey: VZVWQYUYEHMBOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzene, 1-chloro-4-[[(2-chloroethyl)imino]methyl]- 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.0h， 生成 3-(4-chlorophenyl)-2-(N-ethylamino)propan-1-ol
  参考文献：
  名称：

  Transformation of trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-Aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-Aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-Aryl-3-(hydroxymethyl)aziridines

  摘要：

  trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH4 in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.

  DOI：

  10.1021/jo1020932
• 作为产物：
  描述：

  2-氯乙胺盐酸盐 、 4-氯苯甲醛 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以79%的产率得到Benzene, 1-chloro-4-[[(2-chloroethyl)imino]methyl]-
  参考文献：
  名称：

  Transformation of trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-Aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-Aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-Aryl-3-(hydroxymethyl)aziridines

  摘要：

  trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH4 in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.

  DOI：

  10.1021/jo1020932

文献信息

• Transformation of <i>trans</i>-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-Aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-Aryl-2-chloro-3-hydroxypropyl)aziridines and <i>trans</i>-2-Aryl-3-(hydroxymethyl)aziridines
  作者：Karen Mollet、Matthias D’hooghe、Norbert De Kimpe

  DOI：10.1021/jo1020932

  日期：2011.1.7

  trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH4 in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.