N-benzyl-2-(dimethylamino)acetamide | 76733-71-6

• 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: N-benzyl-2-(dimethylamino)acetamide
• 英文别名: N(NN-Dimeam)acetyl)benzylamine
• CAS: 76733-71-6
• 化学式: C₁₁H₁₆N₂O
• mdl: MFCD05124157
• 分子量: 192.261
• InChiKey: OXCIYKRGQKBKTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(dimethylamino)acetamide 、 溴代十二烷 生成 (benzylcarbamoyl-methyl)-dodecyl-dimethyl-ammonium; bromide
  参考文献：
  名称：

  Quaternary ammonium compounds

  摘要：

  公开号：

  US02336179A1
• 作为产物：
  描述：

  N,N-二甲基乙醇胺 、 苄胺 在 3-甲基-2-丁酮 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 caesium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以63%的产率得到N-benzyl-2-(dimethylamino)acetamide
  参考文献：
  名称：

  Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

  摘要：

  A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl-2](2) with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.017
• 作为试剂：
  描述：

  2-氯-4,6-二甲氧基-1,3,5-三嗪 、 苄胺 、 3-苯基丙酸 在 N-benzyl-2-(dimethylamino)acetamide 作用下， 以 甲醇 为溶剂， 以16%的产率得到N-苄基-3-苯基丙酰胺
  参考文献：
  名称：

  Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions

  摘要：

  We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.

  DOI：

  10.1021/jo500376m

文献信息

• Pentacycloundecane derived hydroxy acid peptides: A new class of irreversible non-scissile ether bridged type isoster as potential HIV-1 wild type C-SA protease inhibitors
  作者：Rajshekhar Karpoormath、Yasien Sayed、Patrick Govender、Thavendran Govender、Hendrik G. Kruger、Mahmoud E.S. Soliman、Glenn E.M. Maguire

  DOI：10.1016/j.bioorg.2011.08.002

  日期：2012.2

  Novel peptides incorporating the PCU derived hydroxy acid (5-hydroxy-4-oxahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane) were synthesized and their activity against the resistance-prone wild type C-South African (C-SA) HIV-protease is reported. The attachment of peptides and peptoids to the PCU derived hydroxy acid resulted in a series of structurally diverse promising HIV-1 protease inhibitors. Amongst

  合成了包含PCU衍生的羟基酸（5-羟基-4-氧杂六环[5.4.1.0 2,6 .0 3,10 .0 5,9 .0 8,11 ]十二烷）的新型肽，它们对-易发生野生型C-南非（C-SA）HIV蛋白酶的报道。肽和类肽与PCU衍生的羟基酸的附着导致了一系列结构多样的有希望的HIV-1蛋白酶抑制剂。当中的九个新的化合物，16，17，20和23，得到IC 50相对于野生型C-SA HIV-1蛋白酶而言，其值介于0.6至5.0μM之间。为了了解HIV蛋白酶活性位点上PCU部分的结合模式，已经进行了对接研究和分子动力学（MD）模拟。在所有活性化合物中均观察到PCU衍生的羟基醚与活性位点残基ASP25 / ASP25'之间的氢键保守图谱。
• US6506772B1
  申请人：——

  公开号：US6506772B1

  公开（公告）日：2003-01-14
• Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
  作者：Andrew J.A. Watson、Russell J. Wakeham、Aoife C. Maxwell、Jonathan M.J. Williams

  DOI：10.1016/j.tet.2014.04.017

  日期：2014.6

  A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl-2](2) with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation. (C) 2014 Elsevier Ltd. All rights reserved.
• Quaternary ammonium compounds
  申请人：WINTHROP CHEM CO INC

  公开号：US02336179A1

  公开（公告）日：1943-12-07
• Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions
  作者：Masanori Kitamura、Fumitaka Kawasaki、Kouichi Ogawa、Shuichi Nakanishi、Hiroyuki Tanaka、Kohei Yamada、Munetaka Kunishima

  DOI：10.1021/jo500376m

  日期：2014.4.18

  We studied 1,3,5-triazine-based amide-forming reactions that are mediated or catalyzed by various tert-amines. The representative tert-amine was trimethylamine, which has amido, 1,2,3-triazolyl, aryl, and alkyl linkers. It was found that electron-deficient aryl and heteroaryl linkers, particularly 1,2,3-triazolyl linkers, are superior. On the basis of our findings, we synthesized ligand catalysts, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and found that fluorescent-labeling of a targeting protein using the ligand catalysts proceeded in good yields.