Diisopropyl-N-(2-hydroxyaethyl)-phosphoramidat | 14662-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: Diisopropyl-N-(2-hydroxyaethyl)-phosphoramidat
• 英文别名: N-(2-Hydroxy-aethyl)-phosphorsaeureamid-diisopropylester；(2-hydroxy-ethyl)-amidophosphoric acid diisopropyl ester；Phophorsaeure-(2-hydroxy-aethylamid)-diisopropylester；(2-Hydroxy-aethyl)-amidophosphorsaeure-diisopropylester；2-[Di(propan-2-yloxy)phosphorylamino]ethanol
• CAS: 14662-76-1
• 化学式: C₈H₂₀NO₄P
• 分子量: 225.225
• InChiKey: ZGRLMLWRQWYPGX-UHFFFAOYSA-N

物化性质

• 沸点：
  288.3±42.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diisopropyl-N-(2-hydroxyaethyl)-phosphoramidat 在 盐酸 作用下， 生成 乙醇胺磷酸酯
  参考文献：
  名称：

  A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid

  摘要：

  DOI：

  10.1021/ja01118a524
• 作为产物：
  描述：

  氯磷酸二异丙酯 、 C.I.酸性橙108 在 氯仿 、 三乙胺 作用下， 生成 Diisopropyl-N-(2-hydroxyaethyl)-phosphoramidat
  参考文献：
  名称：

  A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid

  摘要：

  DOI：

  10.1021/ja01118a524

文献信息

• Effect of the structure of phosphylating agents on their reaction with ethanolamine, an ambident nucleophile
  作者：R. Greenhalgh、R. M. Heggie、M. A. Weinberger

  DOI：10.1139/v70-223

  日期：1970.5.1

  The reactions of a series of phosphylating agents (RR′P(O)X) with ethanolamine have been examined, and relative yields of the products from the nucleophilic amino and hydroxyl moieties determined. In general the amount of O-phosphylation increased as R and R′ were changed from dimethylamino through alkoxy to methyl and as the leaving group (X) was changed from OP(O)RR′ to CN. The only exceptions occurred when R was dimethylamino and X was Cl. When X was F, only O-phosphylation was observed. Thus, a wide range of essentially continuously varying selectivities was found.The results are discussed in terms of the amount of charge transfer involved in the formation of the transition state which is assumed to be determined by the electrophile. When the charge transfer is small, the contributions to the activation energy of such factors as solvation and ionization potential of the nucleophile are most important, resulting in N-phosphylation. As the amount of charge transfer increases, the energy of bond formation becomes the dominant factor and O-phosphylation is preferred.

  一系列磷酰化试剂（RR′P(O)X）与乙醇胺的反应已经被研究，确定了来自亲核氨基和羟基的产物的相对产率。一般来说，当R和R′从二甲胺基经过烷氧基变化到甲基时，O-磷酰化的量会增加，当离去基团（X）从OP(O)RR′变化为CN时也会增加。唯一的例外是当R为二甲胺基且X为Cl时。当X为F时，只观察到O-磷酰化。因此，发现了一系列基本连续变化的选择性。结果讨论了在形成过渡态时涉及的电荷转移量，该量被认为由亲电试剂决定。当电荷转移量较小时，诸如溶剂化和亲核试剂的电离势等因素对激活能的贡献最为重要，导致N-磷酰化。随着电荷转移量的增加，键合能量成为主导因素，O-磷酰化更为优先。
• THE PHOSPHORYLATION OF 2-METHYL-Δ²-OXAZOLINE
  作者：R. Greenhalgh

  DOI：10.1139/v62-146

  日期：1962.5.1

  In common with other acylating agents, diisopropyl phosphorochloridate reacts with 2-methyl-Δ²-oxazoline in aqueous and ethereal media to yield N-phosphoryl derivatives. In both media, phosphorylation is followed by ring opening between positions 1 and 5, as shown by the isolation of diisopropyl N-acetyl-N-2-chloroethylphosphoramidate and diisopropyl N-acetyl-N-2-hydroxyethylphosphoramidate. The latter compound undergoes further rearrangement, being slowly converted to diisopropyl N-2-acetoxyethylphosphoramidate in aqueous bicarbonate solution.Nuclear magnetic resonance studies of 2-methyl-Δ²-oxazoline in aqueous bicarbonate solution (pH 8.5) reveal that it is all transformed to N-acetylethanolamine within 23 hours. This short lifetime allows speculation regarding the origin of 2-acetamidoethyl diisopropyl phosphate isolated from the reaction of the base with diisopropyl phosphorofluoridate.

  与其他酰基化试剂一样，二异丙基磷酸氯酯在水和乙醚介质中与2-甲基-Δ²-噁唑啉反应，生成N-磷酰基衍生物。在两种介质中，磷酰化后在1和5位之间发生环开放，如二异丙基N-乙酰-N-2-氯乙基磷酰胺和二异丙基N-乙酰-N-2-羟乙基磷酰胺的分离所示。后者化合物经过进一步的重排，在碳酸氢盐水溶液中缓慢转化为二异丙基N-2-乙酰氧乙基磷酰胺。在pH 8.5的碳酸氢盐水溶液中，2-甲基-Δ²-噁唑啉的核磁共振研究表明，它在23小时内全部转化为N-乙酰乙醇胺。这种短暂的寿命引起了对2-乙酰氨乙基二异丙基磷酸酯的起源的猜测，它是通过碱与二异丙基磷酰氟反应分离出来的。
• Syntheses and biological evaluation of phosphoryl-containing polyunsaturated fatty acid derivatives as hypolipidemic agents
  作者：Fang Hua、Zhang Yiping、Xie Quanling、Huang Xiaoyan、Hong Zhuan

  DOI：10.1080/10426507.2016.1146275

  日期：2016.8.2

  GRAPHICAL ABSTRACT ABSTRACT A series of novel compounds phosphoryl-containing polyunsaturated fatty acid derivatives n-(diisopropoxy-phosphonamide)-alkyl ester (2a–2o) have been synthesized and evaluated for lowering hypolipidemia activities. Amongst all the synthesized compounds, compound 2d, 2h, and 2m showed significant lowering of triglyceride (TG) by 47.37%, 45.88%, and 45.69%, respectively, in

  图形摘要 摘要 一系列含磷酰基的多不饱和脂肪酸衍生物正-（二异丙氧基-膦酰胺）-烷基酯（2a-2o）的新型化合物已被合成并评估用于降低低血脂活性。在所有合成的化合物中，化合物 2d、2h 和 2m 在氚诱导的小鼠高脂血症中分别显着降低了 47.37%、45.88% 和 45.69% 的甘油三酯 (TG)。此外，化合物 2d 显示出有效的抗高血脂活性，并发现在高脂肪饮食诱导的小鼠高脂血症中，血浆总胆固醇水平 (TC) 降低 53.3%，TG 降低 29.3%。
• 一种多不饱和脂肪酰磷脂衍生物及其制备方 法和应用
  申请人：国家海洋局第三海洋研究所

  公开号：CN104910206B

  公开（公告）日：2017-01-18

  本发明公开了一种多不饱和脂肪酰磷脂衍生物及其制备方法与应用，该衍生物的结构通式如下：其中，m＝5或6；n＝2，3或5；k＝2，3，4，5或6；其是将多不饱脂肪酸和磷酰化醇胺混合均匀，在酯缩合剂的作用下制得。本发明不但具有抑制脂肪吸收，促进脂肪水解的功能，而且还能促进脂肪水解并防止脂肪堆积，同时不影响患者的食欲，可被开发成降低血脂、调节饮食失调、治疗超重或肥胖等营养性疾病的药物。
• A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid
  作者：Robert E. Plapinger、T. Wagner-Jauregg

  DOI：10.1021/ja01118a524

  日期：1953.11