4-(2-chloro-5-methylphenyl)morpholine | 122064-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(2-chloro-5-methylphenyl)morpholine
• CAS: 122064-09-9
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: HLAMWYTYUSOKTI-UHFFFAOYSA-N

物化性质

• 沸点：
  339.2±42.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吗啉 、 3-氟-4-氯甲苯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 14.17h， 以77%的产率得到4-(2-chloro-5-methylphenyl)morpholine
  参考文献：
  名称：

  胺与未活化氟苯的碱控制无催化剂N-芳基化反应的机理和范围

  摘要：

  已经开发了一种用于胺类的无过渡金属N芳基化的通用方法。机理研究表明，碱促进所需胺化而不促进不希望的副反应的能力是指导因素。通过使用双（三甲基甲硅烷基）酰胺锂作为碱，所得的去质子化的胺容易与一系列未活化的氟苯衍生物反应。这种新的芳基化方法用于抗抑郁药伏替西汀的简单两步合成。

  DOI：

  10.1002/chem.201604098

文献信息

• [EN] ARYLATION OF ALIPHATIC AMINES<br/>[FR] ARYLATION D'AMINES ALIPHATIQUES
  申请人：AAA CHEMISTRY APS

  公开号：WO2017137047A1

  公开（公告）日：2017-08-17

  The invention relates to a method for arylation of amines, such as aliphatic amines by reaction of aryl-halogens, e.g. chloro- or fluorobenzene derivatives without strongly electron withdrawing substituents in the presence of a strong base.

  这项发明涉及一种方法，用于通过芳基卤代烃（例如氯苯或氟苯衍生物）与强碱在场的情况下对胺进行芳基化，例如脂肪族胺。
• Synthesis of <i>ortho</i>-Haloaminoarenes by Aryne Insertion of Nitrogen–Halide Bonds
  作者：Charles E. Hendrick、Qiu Wang

  DOI：10.1021/jo502541t

  日期：2015.1.16

  A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of NX insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
• Insertion of Arynes into <i>N</i>-Halo Bonds: A Direct Approach to <i>o</i>-Haloaminoarenes
  作者：Charles E. Hendrick、Stacey L. McDonald、Qiu Wang

  DOI：10.1021/ol401518c

  日期：2013.7.5

  A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized a minoarene derivatives.
• ARYLATION OF ALIPHATIC AMINES
  申请人：AAA Chemistry ApS

  公开号：EP3414216A1

  公开（公告）日：2018-12-19