N-[(4-chlorophenyl)diazenyl]-N-methylmethanamine | 7203-90-9

• 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: N-[(4-chlorophenyl)diazenyl]-N-methylmethanamine
• 英文别名: 1-(4-chlorophenyl)-3,3-dimethyltriazene
• CAS: 7203-90-9
• 化学式: C₈H₁₀ClN₃
• 分子量: 183.64
• InChiKey: JZGUQAMYFQKVSO-ZHACJKMWSA-N

物化性质

• 沸点：
  302.33°C (rough estimate)
• 密度：
  1.2295 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[(4-chlorophenyl)diazenyl]-N-methylmethanamine 、 二碳酸二叔丁酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以54%的产率得到N-(t-butoxycarbonyl)-N-methyl(m-chlorobenzyl)amine
  参考文献：
  名称：

  Formation of benzylamines from triazene compounds via a 1,2-proton shift

  摘要：

  A new approach to benzylamines using triazene compounds has been developed that is facilitated by the lithiation of aryltriazenes followed by treatment with an electrophile. The regioselectivity of the reaction can be controlled by means of the substituents in the aryl group. The reaction contains the following steps: intramolecular carbon-carbon bond formation involving lithiation of an alkyl group on a 3-nitrogen atom; a 1,2-proton shift; and the subsequent release of nitrogen gas. Through the use of a deuterated triazene, we were able to determine that the reaction proceeds through a 1,2-proton shift. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.063
• 作为产物：
  描述：

  对氯苯胺 、 二甲胺 在 盐酸 、 sodium nitrite 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.5h， 以100%的产率得到N-[(4-chlorophenyl)diazenyl]-N-methylmethanamine
  参考文献：
  名称：

  1-芳基-3,3-二烷基三氮烯的抗疟活性。

  摘要：

  以100mg / kgbw的腹膜内剂量评估了1-芳基-3，3-二烷基三氮烯对伯氏疟原虫NK-65的抗疟活性。发现其中一些化合物具有有效的抗疟活性。

  DOI：

  10.1016/j.bmc.2007.02.027

文献信息

• FARQUHAR, D.;BENVENUTO, J., J. MED. CHEM., 1984, 27, N 12, 1723-1727
  作者：FARQUHAR, D.、BENVENUTO, J.

  DOI：——

  日期：——
• Antimalarial activity of 1-aryl-3,3-dialkyltriazenes
  作者：Keiji Nishiwaki、Azusa Okamoto、Keizo Matsuo、Yosuke Kawaguchi、Yoshio Hayase、Katsuaki Ohba

  DOI：10.1016/j.bmc.2007.02.027

  日期：2007.4

  The antimalarial activity of 1-aryl-3,3-dialkyltriazenes to Plasmodium berghei NK-65 in infected mice was evaluated at an intraperitoneal dose of 100mg/kgbw. Some of these compounds were found to possess potent antimalarial activity.

  以100mg / kgbw的腹膜内剂量评估了1-芳基-3，3-二烷基三氮烯对伯氏疟原虫NK-65的抗疟活性。发现其中一些化合物具有有效的抗疟活性。
• Formation of benzylamines from triazene compounds via a 1,2-proton shift
  作者：Keiji Nishiwaki、Takashi Ogawa、Kazumi Shigeta、Koichi Takahashi、Keizo Matsuo

  DOI：10.1016/j.tet.2006.04.063

  日期：2006.7

  A new approach to benzylamines using triazene compounds has been developed that is facilitated by the lithiation of aryltriazenes followed by treatment with an electrophile. The regioselectivity of the reaction can be controlled by means of the substituents in the aryl group. The reaction contains the following steps: intramolecular carbon-carbon bond formation involving lithiation of an alkyl group on a 3-nitrogen atom; a 1,2-proton shift; and the subsequent release of nitrogen gas. Through the use of a deuterated triazene, we were able to determine that the reaction proceeds through a 1,2-proton shift. (c) 2006 Elsevier Ltd. All rights reserved.