lithium N-methyl-N-(4-chlorophenyl)amide

• 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: lithium N-methyl-N-(4-chlorophenyl)amide
• 英文别名: N-lithio-N-methyl-p-chloroaniline；lithium;(4-chlorophenyl)-methylazanide
• 化学式: C₇H₇ClN*Li
• 分子量: 147.533
• InChiKey: SMFZWVYEXSKBHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-氯-2,2-二甲基环丙基苯基亚砜 、 lithium N-methyl-N-(4-chlorophenyl)amide 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以9%的产率得到[4-chloro-2-(2,2-dimethylcyclopropyl)phenyl]methylamine
  参考文献：
  名称：

  Cyclopropylation of arylamines at the 2-position with cyclopropylmagnesium carbenoids

  摘要：

  Direct cyclopropylation of arylamines at the 2-position with 1-chlorocyclopropyl phenyl sulfoxides was achieved. The reaction of N-lithio arylamines with cyclopropylinagnesium carbenoids, which are generated from 1-chlorocyclopropyl phenyl sulfoxides with i-PrMgCl via the sulfoxide-magnesium exchange reaction, is the key of this procedure, This method offers an unprecedented way for the synthesis of arylamines having a cyclopropane ring at the 2-position directly from arylamines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.096
• 作为产物：
  描述：

  4-氯-N-甲基苯胺 、 甲基锂 以 乙醚 为溶剂， 反应 6.0h， 生成 lithium N-methyl-N-(4-chlorophenyl)amide
  参考文献：
  名称：

  Ligands with an NPNPN-framework and their application in chromium catalysed ethene tri-/tetramerization

  摘要：

  合成和表征用于铬基选择性乙烯寡聚化的可调配体。

  DOI：

  10.1039/c6dt01109h

文献信息

• Reaction of magnesium carbenoids with N-lithio arylamines: a novel method for generation of non-stabilized α-amino-substituted carbanions and a new synthesis of α-amino acid derivatives
  作者：Tsuyoshi Satoh、Atsushi Osawa、Atsushi Kondo

  DOI：10.1016/j.tetlet.2004.07.069

  日期：2004.8

  with a Grignard reagent at low temperature afforded magnesium carbenoids in quantitative yields. The magnesium carbenoids were found to be reactive with N-lithio alkylamines and N-lithio arylamines. The reaction with N-lithio alkylamines afforded an olefin, which was derived from dimerization of the magnesium carbenoid, in moderate yield. The reaction with N-lithio arylamines gave the adducts, α-amino-substituted

  在低温下用格氏试剂处理1-氯烷基苯基亚砜，以定量收率得到镁类胡萝卜素。发现镁类胡萝卜素可与N-硫代烷基胺和N-硫代芳基胺反应。与N-硫代烷基胺的反应以中等收率得到了烯烃，其衍生自羧甲基镁的二聚。与N-硫代芳基胺的反应以高收率得到加合物α-氨基取代的碳负离子。从这些中间体，实现了α-氨基酸衍生物和在α位具有氘的N，N-二烷基芳基胺的新颖合成。
• From allylic alcohols to chiral tertiary homoallylic alcohol: palladium-catalyzed asymmetric allylation of isatins
  作者：Xiang-Chen Qiao、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1016/j.tetasy.2009.04.012

  日期：2009.6

  A palladium-catalyzed asymmetric allylation of isatins with allylic alcohols as an allyl donor was developed by using chiral spiro phosphoramidite ligands. A variety of chiral tertiary homoallylic alcohols 3-allyl-3-hydroxy-2-oxindoles were prepared directly from allylic alcohols in one step with excellent yields and moderate enantioselectivities. This represents the first catalytic asymmetric allylation

  通过使用手性螺环亚磷酰胺配体，开发了钯催化的靛红与烯丙基醇作为烯丙基供体的不对称烯丙基化反应。一步一步直接从烯丙基醇制备各种手性叔均烯丙基醇3-烯丙基-3-羟基-2-氧吲哚，并具有优异的收率和中等的对映选择性。这代表用烯丙基醇作为烯丙基化剂的酮的第一次催化不对称烯丙基化。
• Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles
  作者：Tsuyoshi Satoh、Mariko Miura、Ken Sakai、Yoshimi Yokoyama

  DOI：10.1016/j.tet.2006.01.080

  日期：2006.4

  Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 degrees C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give alpha-ammo-substituted cyclopropylmagnesiums. The reaction of the a-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. (c) 2006 Elsevier Ltd. All rights reserved.
• Cyclopropylation of arylamines at the 2-position with cyclopropylmagnesium carbenoids
  作者：Yukie Yamada、Mirai Mizuno、Shinobu Nagamoto、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2009.09.096

  日期：2009.11

  Direct cyclopropylation of arylamines at the 2-position with 1-chlorocyclopropyl phenyl sulfoxides was achieved. The reaction of N-lithio arylamines with cyclopropylinagnesium carbenoids, which are generated from 1-chlorocyclopropyl phenyl sulfoxides with i-PrMgCl via the sulfoxide-magnesium exchange reaction, is the key of this procedure, This method offers an unprecedented way for the synthesis of arylamines having a cyclopropane ring at the 2-position directly from arylamines. (C) 2009 Elsevier Ltd. All rights reserved.
• Ligands with an NPNPN-framework and their application in chromium catalysed ethene tri-/tetramerization
  作者：N. Peulecke、B. H. Müller、A. Spannenberg、M. Höhne、U. Rosenthal、A. Wöhl、W. Müller、A. Alqahtani、M. Al Hazmi

  DOI：10.1039/c6dt01109h

  日期：——

  Synthesis and characterization of tunable ligands for chromium based selective oligomerization of ethene.

  合成和表征用于铬基选择性乙烯寡聚化的可调配体。