diethyl {2-[(1,1-dimethylethyl)amino]-2-oxoethyl}phosphonate | 125506-58-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl {2-[(1,1-dimethylethyl)amino]-2-oxoethyl}phosphonate
• 英文别名: N-tert-butyldiethylphosphonoacetamide；N-tert-butyl-2-diethoxyphosphorylacetamide
• CAS: 125506-58-3
• 化学式: C₁₀H₂₂NO₄P
• 分子量: 251.263
• InChiKey: IGWOJNVPBUJEFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl {2-[(1,1-dimethylethyl)amino]-2-oxoethyl}phosphonate 、 (2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.5h， 以17%的产率得到(3R,4E)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[tert-butylcarbamoyl]-pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  直接和非对映选择性合成四官能化硫醇合成子，用于设计金属肽酶抑制剂。

  摘要：

  已经通过简单的非对映选择性和通用方法以良好的产率制备了具有不同侧链的四官能化的含硫醇的合成子。合成的关键步骤包括串联还原反应和Wittig-Horner反应，这保留了起始原料的立体化学。该方法被推广到不同的侧链，使合成用于设计各种锌金属肽酶抑制剂的合成子变得容易。

  DOI：

  10.1016/s0040-4020(99)00922-9
• 作为产物：
  描述：

  N-tert-butyl-2-bromoacetamide 、 亚磷酸三乙酯 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以81%的产率得到diethyl {2-[(1,1-dimethylethyl)amino]-2-oxoethyl}phosphonate
  参考文献：
  名称：

  Microwave-Enhanced Synthesis of Phosphonoacetamides

  摘要：

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.

  DOI：

  10.1080/00397911.2010.530377

文献信息

• Phosphonates α-lithies agents de transfert fonctionnel. Preparation de phosphonates α-amides et d'amides α, β-insatures, α-substitues
  作者：M.K. Tay、E. About-Jaudet、N. Collignon、P. Savignac

  DOI：10.1016/s0040-4020(01)89078-5

  日期：——

  strategy), or by condensation of an amide enolate with diethylchlorophosphate (second strategy). Acidic hydrolysis of () or () gives α-amidophosphonate () alkylated or not in the α -position. () and () react with aromatic or aliphatic aldehydes to produce α,β-unsatured secondary or tertiary amides ().

  仲或叔α-氨基膦酸酯的锂化阴离子（）或（）可通过α-膦酰基碳负离子与异氰酸酯或氨基甲酸酯之间的反应制备（第一种策略），或通过酰胺烯酸酯与二乙基氯磷酸酯的缩合制备（第二种策略）。（）或（）的酸水解产生α-氨基膦酸酯（）在α位上烷基化或未烷基化。（）和（）与芳族或脂族醛反应生成α，β-不饱和仲或叔酰胺（）。
• Efficient method to prepare diethylphosphonacetamides
  作者：Federico Scaravelli、Sergio Bacchi、Luca Massari、Ornella Curcuruto、Pieter Westerduin、William Maton

  DOI：10.1016/j.tetlet.2010.07.125

  日期：2010.9

  An efficient and versatile synthetic method is described to synthesize diethylphosphonacetamides in a single step. (c) 2010 Elsevier Ltd. All rights reserved.
• TAY, M. K.;ABOUT-JAUDET, E.;COLLIGNON, N.;SAVIGNAC, P., TETRAHEDRON, 45,(1989) N4, C. 4415-4430
  作者：TAY, M. K.、ABOUT-JAUDET, E.、COLLIGNON, N.、SAVIGNAC, P.

  DOI：——

  日期：——
• Straightforward and Diastereoselective Synthesis of Tetrafunctionalized Thiol Synthons for the Design of Metallopeptidase Inhibitors
  作者：Christelle David、Laurent Bischoff、Bernard P Roques、Marie-Claude Fournié-Zaluski

  DOI：10.1016/s0040-4020(99)00922-9

  日期：2000.1

  Tetrafunctionalized thiol-containing synthons with different side-chains have been prepared with good yields by a straightforward diastereoselective and general methodology. The key step of the synthesis consisted of a tandem reduction and Wittig–Horner reaction, which conserved the stereochemistry of the starting material. The method was generalized to different side-chains, allowing synthons for

  已经通过简单的非对映选择性和通用方法以良好的产率制备了具有不同侧链的四官能化的含硫醇的合成子。合成的关键步骤包括串联还原反应和Wittig-Horner反应，这保留了起始原料的立体化学。该方法被推广到不同的侧链，使合成用于设计各种锌金属肽酶抑制剂的合成子变得容易。
• Microwave-Enhanced Synthesis of Phosphonoacetamides
  作者：Nadia Gruber、María C. Mollo、Mariana Zani、Liliana R. Orelli

  DOI：10.1080/00397911.2010.530377

  日期：2012.3.1

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.