diethyl (2-(benzylamino)-2-oxoethyl)phosphonate | 183444-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl (2-(benzylamino)-2-oxoethyl)phosphonate
• 英文别名: N-benzyl-2-diethoxyphosphorylacetamide
• CAS: 183444-23-7
• 化学式: C₁₃H₂₀NO₄P
• 分子量: 285.28
• InChiKey: QBIQHYHNTQWBGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-(benzylamino)-2-oxoethyl)phosphonate 在 (1R,4R,7R)-N-(tert-butyl)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2 carboxamide 、 lithium bromide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 44.27h， 生成 N-benzyl-4-methyl-3-phenylpentanamide
  参考文献：
  名称：

  手性纳米粒子/路易斯酸作为α，β-不饱和酰胺不对称1,4-加成芳硼酸的协同催化剂

  摘要：

  已经开发了由手性Rh / Ag纳米粒子和Sc（OTf）3组成的协同催化剂，可有效催化芳基硼酸与α，β-不饱和酰胺的不对称1,4加成反应。由于酰胺底物的低反应性，该反应被认为是最具挑战性的反应之一。在催化剂的低负载量（＜0.5mol％）的存在下，新型催化剂为所需产物提供了优异的对映选择性（＞ 98％  ee）。

  DOI：

  10.1002/anie.201601559
• 作为产物：
  描述：

  二乙基磷乙酸 、 苄胺 在 1-丙基磷酸酐 作用下， 以 乙酸乙酯 为溶剂， 以80%的产率得到diethyl (2-(benzylamino)-2-oxoethyl)phosphonate
  参考文献：
  名称：

  Efficient method to prepare diethylphosphonacetamides

  摘要：

  An efficient and versatile synthetic method is described to synthesize diethylphosphonacetamides in a single step. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.125

文献信息

• A Powerful Hydrogen-Bond-Donating Organocatalyst for the Enantioselective Intramolecular Oxa-Michael Reaction of α,β-Unsaturated Amides and Esters
  作者：Yusuke Kobayashi、Yamato Taniguchi、Noboru Hayama、Tsubasa Inokuma、Yoshiji Takemoto

  DOI：10.1002/anie.201305492

  日期：2013.10.11

  Tuning the organocatalyst: An unprecedented enantioselective intramolecular oxa‐Michael reaction of unactivated α,β‐unsaturated amides and esters catalyzed by a powerful hydrogen‐bond‐donating organocatalyst has been developed. Furthermore, the products obtained from this reaction have been used for the straightforward asymmetric synthesis of several natural products and biologically important compounds

  调节有机催化剂：已开发出前所未有的对映体选择性分子内氧杂-Michael反应，该反应由强大的给氢键有机催化剂催化，未活化的α，β-不饱和酰胺和酯。此外，从该反应获得的产物已经用于几种天然产物和生物学上重要的化合物的直接不对称合成。
• Sulfur-Assisted Propargyl−Allenyl Isomerizations and Electrocyclizations for the Convenient and Efficient Synthesis of Polyfunctionalized Benzenes and Naphthalenes
  作者：Hongwei Zhou、Yanpeng Xing、Jinzhong Yao、Junhui Chen

  DOI：10.1021/ol101479d

  日期：2010.8.20

  A facile and efficient electrocyclization for the synthesis of polyfunctionalized benzene and naphthalene derivatives was reported. As a result of the ready availability of starting materials and simple operation, this type of reaction has potential utility in organic synthesis.
• 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.