(S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol | 1378030-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol
• 英文别名: (S)-2-[2-(diethoxyphosphoryl)acetamide] 2-benzylethanol；2-diethoxyphosphoryl-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]acetamide
• CAS: 1378030-79-5
• 化学式: C₁₅H₂₄NO₅P
• 分子量: 329.333
• InChiKey: CYQOSFKLAHNJNV-AWEZNQCLSA-N

物化性质

• 沸点：
  549.0±50.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol 在 氯化亚砜 、 三乙胺 、 sodium bromide 作用下， 反应 3.25h， 以80%的产率得到(S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylbromopropane
  参考文献：
  名称：

  Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides

  摘要：

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.003
• 作为产物：
  描述：

  methyl (2-chloroacetyl)-L-phenylalaninate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 1.5h， 生成 (S)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol
  参考文献：
  名称：

  通过 Michaelis-Arbuzov 反应合成 α-氨基膦酸酯的有效方法

  摘要：

  摘要 以氨基酯和氯乙酰氯为原料，采用一种高效的方法合成了一系列新的改性α-酰胺基膦酸酯（或β-酮基膦酸酯）。我们已经确定氯乙酰氯是一种合适的试剂，可以为 Arbuzov 反应引入卤素部分。α-氨基膦酸盐分两步（乙酰化、磷酸化）制备。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要

  DOI：

  10.1080/10426507.2011.645173

文献信息

• A novel, rapid and green method of phosphorylation under ultrasound irradiation and catalyst free conditions
  作者：Abdeslem Bouzina、Billel Belhani、Nour-Eddine Aouf、Malika Berredjem

  DOI：10.1039/c5ra06380a

  日期：——

  Phosphorylation of N-acylamines, N-acylaminoesters, N-acylaminoalcohols and N-acylsulfonamides with trialkylphosphite was promoted under ultrasound irradiation using solvent and catalyst free conditions to afford amidophosponates with 75–90% yield in 5–15 min.

  使用超声波辐照在无溶剂和催化剂的条件下促进三烷基磷酸酯对N-酰胺、N-酰氨酯、N-酰氨醇和N-酰磺酰胺的磷酸化反应，产率为75-90%，反应时间为5-15分钟，得到酰胺磷酸酯。
• Synthesis, antimycobacterial and cytotoxic activity of α,β-unsaturated amides and 2,4-disubstituted oxazoline derivatives
  作者：Francisco G. Avalos-Alanís、Eugenio Hernández-Fernández、Pilar Carranza-Rosales、Susana López-Cortina、Jorge Hernández-Fernández、Mario Ordóñez、Nancy E. Guzmán-Delgado、Alejandro Morales-Vargas、Víctor M. Velázquez-Moreno、María G. Santiago-Mauricio

  DOI：10.1016/j.bmcl.2017.01.024

  日期：2017.2

  The synthesis of six α,β,-unsaturated amides and six 2,4-disubstituted oxazolines derivatives and their evaluation against two Mycobacterium tuberculosis strains (sensitive H37Rv and a resistant clinical isolate) is reported. 2,4-Disubstituted oxazolines (S)-3b,d,e were the most active in the sensitive strain with a MIC of 14.2, 13.6 and 10.8μM, respectively, and the compounds (S)-3d,f were the most

  报道了六个α，β，不饱和酰胺和六个2，4-二取代的恶唑啉衍生物的合成及其对两种结核分枝杆菌菌株（敏感的H37Rv和耐药的临床分离株）的评价。2,4-二取代恶唑啉（S）-3b，d，e在敏感菌株中活性最高，MIC分别为14.2、13.6和10.8μM，化合物（S）-3d，f最活跃MIC分别为6.8和7.4μM的抗性菌株。还对α，β-不饱和酰胺（S）-2b和（S）-2d，f以及恶唑啉（S）-3b和（S ）-3d，f（5、15和30μg/ mL）。结果表明这些化合物具有有希望的抗分枝杆菌活性，同时没有肝毒性。
• Efficient Method for The Synthesis of α-Amidophosphonates via the Michaelis-Arbuzov Reaction
  作者：Samia Guezane Lakoud、Malika Berredjem、Nour-Eddine Aouf

  DOI：10.1080/10426507.2011.645173

  日期：2012.6

  from aminoesters and chloroacetyl chloride. We have established that chloroacetyl chloride is a suitable reagent allowing the introduction a halogen moiety for the Arbuzov reaction. The α-amidophosphonates were prepared in two steps (acetylation, phosphorylation). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related

  摘要 以氨基酯和氯乙酰氯为原料，采用一种高效的方法合成了一系列新的改性α-酰胺基膦酸酯（或β-酮基膦酸酯）。我们已经确定氯乙酰氯是一种合适的试剂，可以为 Arbuzov 反应引入卤素部分。α-氨基膦酸盐分两步（乙酰化、磷酸化）制备。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides
  作者：Francisco G. Avalos-Alanís、Eugenio Hernández-Fernández、Rocio Hernández-Romero、Susana López-Cortina、Mario Ordóñez、Oscar García-Barradas、Selene Lagunas-Rivera

  DOI：10.1016/j.tetasy.2013.12.003

  日期：2014.1

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.