diethylamidooxalyl chloride | 87039-68-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethylamidooxalyl chloride
• 英文别名: diethylaminooxalyl chloride；2-(diethylamino)-2-oxoacetyl chloride；ClCOCONEt2；Diaethyl-oxalamoylchlorid；N,N-(diethylamino)(oxo)acetyl chloride；Oxalsaeure-chlorid-diaethylamid；Diaethyloxamidsaeure-chlorid；Acetyl chloride, (diethylamino)oxo-
• CAS: 87039-68-7
• 化学式: C₆H₁₀ClNO₂
• 分子量: 163.604
• InChiKey: QTDZPCPIVFIEHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diethylamidooxalyl chloride 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 2-(2-(2-(diethylamino)-2-oxoacetamido)propan-2-yl)-4-(4-fluorobenzylcarbamoyl)-6-methoxypyrimidin-5-yl benzoate
  参考文献：
  名称：

  Hydroxyl may not be indispensable for raltegravir: Design, synthesis and SAR Studies of raltegravir derivatives as HIV-1 inhibitors

  摘要：

  A series of raltegravir derivatives 20-42 were prepared and systematically evaluated for their anti-HIV activity. The bioassay results showed that most of the compounds possess good to excellent anti-HIV activity. Especially, compounds 25 and 35 with subpicomole IC50 values seemed to be the most potent anti-HIV agents among all of the reported synthesized compounds. These compounds may therefore be considered as new potent anti-HIV agents. The 5-hydroxyl modification of raltegravir derivatives significantly increased the anti-HIV activity, which indicates that the hydroxyl may not be indispensable for raltegravir. The introducing of acyl at 5-position of raltegravir derivatives is favorable for antiviral activity. In addition, a high-throughput cell-based assay method with pseudotyped virus stocks was developed and used to identify HIV inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.015
• 作为产物：
  描述：

  N,N-二乙基草氨酸乙酯 在 氯化亚砜 、 sodium hydroxide 作用下， 反应 9.0h， 生成 diethylamidooxalyl chloride
  参考文献：
  名称：

  设计，合成，结构，和新的含草酰部分的螺环四氢苯甲酸衍生物的杀螨/杀虫活性。

  摘要：

  通过关键中间体3-（2,4,6-三甲基）-2-oxo-1-oxaspiro [4.4] -decyl-3-en-4设计并合成了一系列含有草酰部分的新型螺环四酸衍生物-ol。通过1 H NMR和元素分析或高分辨率质谱（HRMS）鉴定目标化合物。生物测定的结果表明，大多数目标化合物对胭脂红蜘蛛幼虫和卵具有出色的杀螨活性。特别是二异丙基氨基草酰化合物7g和哌啶草酰化合物7h分别是市售Spiromesifen对红蜘蛛卵的活性的1.4倍和2.3倍。而且，大多数目标化合物对鳞翅目害虫表现出杀虫活性。有趣的是，含有烷基氨基取代的草酰部分的化合物在红蜘蛛幼虫和卵之间显示出明显的选择性，因为对7g和7h的红蜘蛛卵的活性是对红蜘蛛幼虫的25倍，而Spiromesifen在这些活性上没有显着差异。这意味着将草酰部分引入螺环四氢苯甲酸可能会导致新的生物活性特征。

  DOI：

  10.1021/jf203722z

文献信息

• Conversion of Hydroxyl Groups in Alcohols to Other Functional Groups with<i>N</i>-Hydroxy-2-thiopyridone, and Its Application to Dialkylamines and Thiols
  作者：Hideo Togo、Misa Fujii、Masataka Yokoyama

  DOI：10.1246/bcsj.64.57

  日期：1991.1

  The radical decarboxylation reaction of N-alkoxyoxalyloxy-2-thiopyridone which was prepared by the reaction of alcohol, oxalyl chloride, and N-hydroxy-2-thiopyridone was studied both in the absence and presence of olefinic compounds. The same reactions with olefinic and acetylenic alcohols gave the corresponding lactone derivatives. On the other hand the unsymmetrical alkyl 2-pyridyl disulfides were obtained by the same reaction with aliphatic thiols.

  对由醇、草酰氯和N-羟基-2-噻吩酮反应制备的N-烷氧基草酰氧基-2-噻吩酮的还原脱羧反应进行了研究，无论是在没有还是有烯烃化合物存在的情况下。同样，与烯醇和炔醇的反应得到了相应的内酯衍生物。另一方面，通过与脂肪族硫醇的相同反应得到了不对称的烷基-2-吡啶基二硫化物。
• Novel Synthesis of 2-Oxo-3-butynoates by Copper-Catalyzed Cross-Coupling Reaction of Terminal Alkynes and Monooxalyl Chloride
  作者：Minjie Guo、Dao Li、Zhaoguo Zhang

  DOI：10.1021/jo0353076

  日期：2003.12.1

  A general and efficient Cu(I)-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride for the synthesis of 2-oxo-3-butynoates and 2-oxo-3-butynoamides was developed. Readily available starting materials, the mild reaction conditions, wide functional group tolerance, and the obviation of stoichiometric organolithium or magnesium reagents combine to highlight this reaction.

  开发了通用有效的末端炔烃和单草酰氯的Cu（I）催化交叉偶联反应，用于合成2-oxo-3-butynoates和2-oxo-3-butynoamides。易于获得的起始原料，温和的反应条件，宽泛的官能团耐受性以及对化学计量的有机锂或镁试剂的避免，共同突出了该反应。
• HIV INTEGRASE INHIBITORS
  申请人：Summa Vincenzo

  公开号：US20090221571A1

  公开（公告）日：2009-09-03

  Pyridopyrimidine carboxamide compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的吡啶基嘧啶羧酰胺化合物是HIV整合酶的抑制剂，也是HIV复制的抑制剂：其中R1、R2、R3、R4、R5和R6在此被定义。这些化合物可用于预防或治疗HIV感染，以及预防、治疗或延缓艾滋病的发作。这些化合物可作为药物本身或作为药学上可接受的盐形式用于对抗HIV感染和艾滋病。这些化合物及其盐可用作药物组合物的成分，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。
• Cleavage of silicon-nitrogen bonds by acid chlorides: an unusual synthetic route to amides
  作者：James R. Bowser、Pamela J. Williams、Kenneth Kurz

  DOI：10.1021/jo00170a050

  日期：1983.11
• Copper-Catalyzed Oxalamide-Directed <i>ortho</i>-C–H Amination of Anilines with Alkylamines
  作者：Peng Wu、Wei Huang、Tai-Jin Cheng、Hai-Xia Lin、Hui Xu、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.0c01632

  日期：2020.7.2

  A copper-catalyzed oxalamide-directed ortho-C-H amination of anilines has been developed by using 1 atm of air as the sole oxidant. The protocol shows excellent functional group tolerance, and some heterocyclic amines including indole, benzothiophene, benzothiazole, quinoline, isoquinoline, and quinoxaline could be compatible in the reaction. The late-stage diversification of medicinal drugs demonstrates the synthetic utility of this protocol.