N-(4-Cyano-phenyl)-acetamidine; hydrochloride | 1002107-29-0

• 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-Cyano-phenyl)-acetamidine; hydrochloride
• 英文别名: N'-(4-cyanophenyl)ethanimidamide
• CAS: 1002107-29-0
• 化学式: C₉H₉N₃
• 分子量: 159.191
• InChiKey: KGFNIAGZEZNIKD-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  272.6±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮基乙酰乙酸乙酯 、 N-(4-Cyano-phenyl)-acetamidine; hydrochloride 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 cesium acetate 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以80%的产率得到ethyl 5-cyano-2-methyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  钌（II）催化的咪唑和异氰酸酯与重氮化合物的CH活化：吲哚和3H吲哚的底物控制合成

  摘要：

  吲哚是生物活性分子中常见的重要结构基序。在这项工作中，开发了酰亚胺酰胺和受体-受体重氮化合物之间发散偶联的条件，该条件可在钌催化下提供NH吲哚和3 H-吲哚。α-二氮杂酮酸酯的偶联通过裂解C（N 2）-C（酰基）键提供了NH吲哚，而α-二氮杂丙二酸酯通过C-N键的裂解产生了3个H-吲哚。该反应通过钌催化的CH活化作用构成重氮底物与芳烃的第一个分子间偶联。

  DOI：

  10.1002/anie.201606316
• 作为产物：
  描述：

  乙腈 、 对氨基苯腈 在 盐酸 作用下， 反应 4.5h， 以90%的产率得到N-(4-Cyano-phenyl)-acetamidine; hydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents

  摘要：

  Several compounds of great pharmacological interest contain the triazole and imidazole rings. In order to find new drugs with antileishmanial activity we have synthesized and evaluated new imidazole and triazole compounds carrying either the carbaldehyde or the difluoromethylene functionalities against promastigote forms of Leishmania amazonensis. Among the compounds tested difluoromethylene azoles 4b and 8f have inhibited the parasite growth significantly. Our results show that the introduction of the difluoromethylene moieties has turned the inactive carbaldehydes into active antileishmanial compounds. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.020

文献信息

• Reactivity-Controlled Regioselectivity: A Regiospecific Synthesis of 1,2-Disubstituted Benzimidazoles
  作者：Xiaohu Deng、Neelakandha S. Mani

  DOI：10.1002/ejoc.200901056

  日期：2010.2

  combination of N 1 /N 2 chemoselectivity on the amidine and reactivity-controlled X 1 /X 2 chemoselectivity on the 1,2-dihaloarene. This reaction proves to be fairly general for the regiospecific synthesis of 1,2-substituted benzimidazoles.

  我们在 1,2-分化二卤代芳烃和 N-取代脒之间的串联胺化反应中展示了卓越的区域选择性。这种CuI催化反应的区域化学结果是通过脒的N 1 /N 2 化学选择性和1,2-二卤代芳烃的反应性控制的X 1 /X 2 化学选择性的组合实现的。该反应证明对于 1,2-取代苯并咪唑的区域特异性合成是相当普遍的。
• PROCESS FOR THE PREPARATION OF ETRAVIRINE AND INTERMEDIATES IN THE SYNTHESIS THEREOF
  申请人：MAJER Maja Sepelj

  公开号：US20130123498A1

  公开（公告）日：2013-05-16

  The present invention includes compounds of Formula 1 of the following structure: or salts thereof, wherein X is a halogen or a tosyl group. Processes for preparing the compounds of Formula 1 are disclosed in the patent application. The compounds of Formula 1 are useful as intermediates for preparation of Etravirine. The present invention is also directed toward processes for preparing Etravirine.

  本发明包括以下结构的公式1的化合物：或其盐，其中X是卤素或tosyl基团。专利申请中公开了制备公式1化合物的过程。公式1化合物可用作Etravirine制备的中间体。本发明还涉及制备Etravirine的过程。
• PROCESS FOR THE PREPARATION AND PURIFICATION OF ETRAVIRINE AND INTERMEDIATES THEREOF
  申请人：Krizmanic Irena

  公开号：US20110275812A1

  公开（公告）日：2011-11-10

  In one embodiment the present invention encompasses 4-(2,6-dichloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile (“ETHER”), 4-(4,6-dichloropyrimidin-2-yloxy)-3,5-dimethyl-benzonitrile (“ETHER C-2 isomer”), mixtures and salts thereof of. The present invention encompasses the use of ETHER and salts thereof to prepare Etravirine and Etravirine intermediates, and salts thereof. In another embodiment the present invention encompasses the use of ETHER and salts thereof to prepare debrometravirine (“DEBETV”) and salts thereof. In yet another embodiment the present invention encompasses the use of ETHER and salts thereof to prepare 4-(6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile (“ARCPBN”) and salts thereof. The compound, 4-(2,6-dichloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile “ETHER” of formula (A) wherein n is either 0 or 1 and HA is an acid.
• US8153790B2
  申请人：——

  公开号：US8153790B2

  公开（公告）日：2012-04-10
• Ruthenium(II)‐Catalyzed C−H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate‐Controlled Synthesis of Indoles and 3 <i>H</i> ‐Indoles
  作者：Yunyun Li、Zisong Qi、He Wang、Xifa Yang、Xingwei Li

  DOI：10.1002/anie.201606316

  日期：2016.9.19

  Indoles are an important structural motif that is commonly found in biologically active molecules. In this work, conditions for divergent couplings between imidamides and acceptor–acceptor diazo compounds were developed that afforded NH indoles and 3H‐indoles under ruthenium catalysis. The coupling of α‐diazoketoesters afforded NH indoles by cleavage of the C(N2)−C(acyl) bond whereas α‐diazomalonates

  吲哚是生物活性分子中常见的重要结构基序。在这项工作中，开发了酰亚胺酰胺和受体-受体重氮化合物之间发散偶联的条件，该条件可在钌催化下提供NH吲哚和3 H-吲哚。α-二氮杂酮酸酯的偶联通过裂解C（N 2）-C（酰基）键提供了NH吲哚，而α-二氮杂丙二酸酯通过C-N键的裂解产生了3个H-吲哚。该反应通过钌催化的CH活化作用构成重氮底物与芳烃的第一个分子间偶联。