ethyl 2-(diallylamino)-2-oxoacetate | 36342-06-0

• 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: ethyl 2-(diallylamino)-2-oxoacetate
• 英文别名: Acetic acid, (di-2-propenylamino)oxo-, ethyl ester；ethyl 2-[bis(prop-2-enyl)amino]-2-oxoacetate
• CAS: 36342-06-0
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: ZDJOYLZBTPINCT-UHFFFAOYSA-N

物化性质

• 沸点：
  255.1±43.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(diallylamino)-2-oxoacetate 在 氨 、 溶剂黄146 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-(3-methylphenyl)-N,N-bis(prop-2-enyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Practical Synthesis of Functionalized 1,5-Disubstituted 1,2,4-Triazole Derivatives

  摘要：

  A general approach for the synthesis of 1,5-disubstituted-1,2,4-triazole compounds is described. A series of new oxamide-derived amidine reagents can be accessed in excellent yield with minimal purification necessary. Typically, these amidine reagents are stable crystalline solids and in certain cases were found to exist in a cyclic form as determined by NMR spectroscopy. Under optimized conditions, the direct reaction of these prepared reagents with various hydrazine hydrochloride salts efficiently generates the target triazoles. Both aromatic and aliphatic hydrazines react readily with the amidine reagents under very mild reaction conditions, delivering desired 1,5-disubstituted-1,2,4-triazole derivatives in good yields.

  DOI：

  10.1021/jo1017603
• 作为产物：
  描述：

  草酰氯单乙酯 、 二烯丙基胺 以 二氯甲烷 为溶剂， 以98%的产率得到ethyl 2-(diallylamino)-2-oxoacetate
  参考文献：
  名称：

  Practical Synthesis of Functionalized 1,5-Disubstituted 1,2,4-Triazole Derivatives

  摘要：

  A general approach for the synthesis of 1,5-disubstituted-1,2,4-triazole compounds is described. A series of new oxamide-derived amidine reagents can be accessed in excellent yield with minimal purification necessary. Typically, these amidine reagents are stable crystalline solids and in certain cases were found to exist in a cyclic form as determined by NMR spectroscopy. Under optimized conditions, the direct reaction of these prepared reagents with various hydrazine hydrochloride salts efficiently generates the target triazoles. Both aromatic and aliphatic hydrazines react readily with the amidine reagents under very mild reaction conditions, delivering desired 1,5-disubstituted-1,2,4-triazole derivatives in good yields.

  DOI：

  10.1021/jo1017603

文献信息

• Pd/C-Catalyzed Synthesis of Oxamates by Oxidative Cross Double Carbonylation of Amines and Alcohols under Co-catalyst, Base, Dehydrating Agent, and Ligand-Free Conditions
  作者：Sandip T. Gadge、Bhalchandra M. Bhanage

  DOI：10.1021/jo401038e

  日期：2013.7.5

  This work reports a mild, efficient, and ligand-free Pd/C-catalyzed protocol for the oxidative cross double carbonylation of amines and alcohols. Notably, the reaction does not requires any base, co-catalyst, dehydrating agent, or ligand. Pd/C solves the problem of catalyst recovery, and the catalyst was recycled up to six times.

  这项工作报告了一种温和，有效且无配体的Pd / C催化方案，用于胺和醇的氧化交叉双羰基化。值得注意的是，该反应不需要任何碱，助催化剂，脱水剂或配体。Pd / C解决了催化剂回收的问题，并且催化剂循环使用多达六次。
• Bentz,F.; Nischk,G.-E., Angewandte Chemie, 1970, vol. 82, p. 80
  作者：Bentz,F.、Nischk,G.-E.

  DOI：——

  日期：——
• Practical Synthesis of Functionalized 1,5-Disubstituted 1,2,4-Triazole Derivatives
  作者：Yingju Xu、Mark McLaughlin、Emily N. Bolton、Robert A. Reamer

  DOI：10.1021/jo1017603

  日期：2010.12.17

  A general approach for the synthesis of 1,5-disubstituted-1,2,4-triazole compounds is described. A series of new oxamide-derived amidine reagents can be accessed in excellent yield with minimal purification necessary. Typically, these amidine reagents are stable crystalline solids and in certain cases were found to exist in a cyclic form as determined by NMR spectroscopy. Under optimized conditions, the direct reaction of these prepared reagents with various hydrazine hydrochloride salts efficiently generates the target triazoles. Both aromatic and aliphatic hydrazines react readily with the amidine reagents under very mild reaction conditions, delivering desired 1,5-disubstituted-1,2,4-triazole derivatives in good yields.